Standard Article

Oxidation of Carbonyl Compounds with Organohypervalent Iodine Reagents

  1. Robert M. Moriarty,
  2. Om Prakash

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or054.02

Organic Reactions

Organic Reactions

How to Cite

Moriarty, R. M. and Om Prakash 2004. Oxidation of Carbonyl Compounds with Organohypervalent Iodine Reagents. Organic Reactions. 54:2:273–418.

Author Information

  1. The University of Illinois at Chicago, Department of Chemistry, Chicago, USA

  1. (On sabbatical leave from Kurukshetra University, Kurukshetra, Haryana, 136119 INDIA)

Publication History

  1. Published Online: 15 APR 2004

Chemistry Terms

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Abstract

The search for novel oxidizing agents, especially those that not only transform a broad range of diverse functional groups, but also do so with a high degree of selectivity, remains the focus of intense exploration. In recent years, the use of hypervalent iodine compounds as oxidizing agents has gained attention in synthetic organic chemistry. The α-oxidation of carbonyl compounds by hypervalent iodine oxidants has been most widely investigated and has broad synthetic utility. Although this area has recently been reviewed in various forms and scope, a comprehensive coverage that focuses on synthetic applications is absent and the present chapter addresses this need.

In this chapter the oxidation of carbonyl compounds with hypervalent iodine reagents is discussed. These reagents effect the electrophilic α-oxidation of large numbers of ketones, β-diketones, α,β-unsaturated ketones, and their derivatives such as silyl enol ethers. The discussion is restricted mainly to the reactions of organoiodine(III) reagents; inclusion of other hypervalent iodine reagents such as organoiodine(V) reagents, periodic acid, or purely inorganic iodate reagents is beyond the scope of this chapter. Furthermore, reactions brought about with other oxidizing agents in combination with a catalytic amount of a hypervalent iodine reagent are not considered here. The chapter also excludes discussion of a considerable amount of work based upon the reaction of iodonium ylides, a distinct feature of organoiodine(III) reagents. The common abbreviations and names of the reagents used in this chapter are listed.

A general feature of the reactions of carbonyl compounds described in this chapter is electrophilic attack of the organoiodine(III) reagent at the α-carbon atom of a carbonyl group to yield a presumed tricoordinate iodine(III) intermediate.

The Intermediate reacts further to yield products via various pathways depending upon the reaction conditions. The major processes that occur are summarized. These include oxidation of ketones under basic conditions leading to α-hydroxydimethylacetals, oxidation of α,β-unsaturated ketones leading to α-hydroxy-β-methoxydimethylacetals, oxidation of ketones under neutral conditions, and related oxidation of silyl enol ethers under various conditions leading to α-functionalization, intramolecular participation reactions leading to oxygen-containing heterocyclic compounds including cyclic α-keto ethers and lactones, and rearrangement processes such as 1,2-aryl shifts in alkyl aryl ketones leading to 2-arylalkanoates. All of these reactions are driven by the reduction of iodine(III) to iodine(I) (iodobenzene).

Keywords:

  • hypervalent iodine reagents;
  • mechanisms;
  • pathways;
  • oxidation;
  • basic conditions;
  • neutral conditions;
  • aprotic solvents;
  • silyl enol ethers;
  • intramolecular participation;
  • rearrangement processes;
  • scope;
  • limitations;
  • functionalization;
  • carbonyl compounds;
  • hydroxylation;
  • arylation;
  • acidic conditions;
  • acetoxylation;
  • sulfonoxylation;
  • tosyloxylation;
  • phosphorloxylation;
  • silyl enol ethers;
  • ketene silyl acetals;
  • alkoxylation;
  • carbon-carbon bonds;
  • functionalization;
  • dicarbonyl compounds;
  • intramolecular reactions;
  • oxygen heterocyclic compounds;
  • halogenation;
  • imidylation;
  • ketones;
  • rearrangements;
  • dehydrogenation;
  • comparison of methods;
  • experimental procedures;
  • tabular survey

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.965
Molecular Formula:CHArO2
InChIKey:QFPDXXKZGYMSLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.3602
Molecular Formula:C11H20O3Si
InChIKey:PFGZATNDBDRWHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.1871
Molecular Formula:C12H11O4P
InChIKey:Not Available
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:RBMWDBHKRZTOMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.1816
Molecular Formula:C10H13O4P
InChIKey:RJLHEGRODLLJFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:MCIIDRLDHRQKPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.942
Molecular Formula:C3H2Ar2O3
InChIKey:UJEGGAUFZPSFPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:BUZYGTVTZYSBCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.429
Molecular Formula:C18H22O5S
InChIKey:AYXDDWBZCHWXDJ-RDTXWAMCSA-N
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Compound Information
Molecular Weight:452.304
Molecular Formula:C16H21IO5S
InChIKey:GALXPSZVMHCBND-MLGOLLRUSA-N
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Compound Information
Molecular Weight:136.947
Molecular Formula:C2H3Ar2NO
InChIKey:ZJUTYNFQSUCPFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:442.4615
Molecular Formula:C30H18O4
InChIKey:PHJGSPFWJMKOIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:SBZXBUIDTXKZTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1553
Molecular Formula:C6H15O3P
InChIKey:BDZBKCUKTQZUTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.3927
Molecular Formula:C19H24O2
InChIKey:YEWSFUFGMDJFFG-QAGGRKNESA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:BEKNOGMQVKBMQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.2381
Molecular Formula:C15H10O3
InChIKey:HVQAJTFOCKOKIN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.118
Molecular Formula:C4H8ArOS
InChIKey:KTYJRWGYGYIKJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.264
Molecular Formula:C10H12O5S
InChIKey:CXCJKSOSQLMDDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:DULCUDSUACXJJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.2796
Molecular Formula:C13H17NO2
InChIKey:FUFXUDYTHVEYBS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:SBQNJPMENLLVNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:281.1123
Molecular Formula:C12H10I
InChIKey:OZLBDYMWFAHSOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.932
Molecular Formula:C2H2Ar2O2
InChIKey:RJDZQQPKCQHWKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.334
Molecular Formula:C15H14O4S
InChIKey:QDSBRLMOWFYBGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.238
Molecular Formula:C9H10O4S
InChIKey:PGKMWTAFZUKYBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.955
Molecular Formula:ArHO
InChIKey:WGTVBBMGNNJOKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:430.0392
Molecular Formula:C10H5F6IO4
InChIKey:PEZNEXFPRSOYPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:369.1749
Molecular Formula:C15H15IO3
InChIKey:CPKUMQYSOYVPSB-UHFFFAOYSA-M
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:NTIZESTWPVYFNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.1834
Molecular Formula:C10H10O5
InChIKey:NBZHIYIFEZPJML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.2461
Molecular Formula:C15H11O2
InChIKey:SMKGKJNRNQTQBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3016
Molecular Formula:C15H18O3
InChIKey:JLKRDWNOCHSCKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:470.1949
Molecular Formula:C18H16IO5P
InChIKey:QUAVIMICLVDXIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:MGKPCLNUSDGXGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3556
Molecular Formula:C12H18O2Si
InChIKey:OBSDFVRTHOESNN-BENRWUELSA-N
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Compound Information
Molecular Weight:427.2545
Molecular Formula:C21H16IO2
InChIKey:KERIKOVYQFJVQY-CTNGQTDRSA-N
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Compound Information
Molecular Weight:388.5402
Molecular Formula:C24H36O4
InChIKey:FXAUDDYLUQUASD-GIDXXXHDSA-N
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Compound Information
Molecular Weight:235.345
Molecular Formula:C13H17NOS
InChIKey:FASGPVPLRRSHIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.3347
Molecular Formula:C21H14O2
InChIKey:FEKIAHWXEOWQJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.3235
Molecular Formula:C9H18O2Si
InChIKey:QFTZNDXGRJJETP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:271.3541
Molecular Formula:C17H21NO2
InChIKey:YRDXHIRGZLDDMU-ZACQAIPSSA-N
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Compound Information
Molecular Weight:140.067
Molecular Formula:C3H2ArNOS
InChIKey:VNEFQWKBVCBTKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2969
Molecular Formula:C8H16O2Si
InChIKey:FTXCTXYJXIABGR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:240.2524
Molecular Formula:C12H16O5
InChIKey:ALJLBTXSMIHRPF-GHMZBOCLSA-N
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Compound Information
Molecular Weight:346.3142
Molecular Formula:C18H19O5P
InChIKey:OLDODCGSYVHLKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1421
Molecular Formula:C9H6O3
InChIKey:DCMHKQKYWBSFKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1427
Molecular Formula:C9H6O2
InChIKey:OTAFHZMPRISVEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:FFNOWYSCJOKVCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:CRZQGDNQQAALAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.4122
Molecular Formula:C13H24O5Si
InChIKey:CNLJXOMJNNRSAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2387
Molecular Formula:C15H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:GXHFUVWIGNLZSC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.0233
Molecular Formula:C2HF3O2
InChIKey:DTQVDTLACAAQTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2818
Molecular Formula:C16H14O
InChIKey:CVZWTVDMZYGOSX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:297.413
Molecular Formula:C15H23NO3S
InChIKey:GZWNEILFIDWMOI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:Not Available
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Compound Information
Molecular Weight:286.4085
Molecular Formula:C19H26O2
InChIKey:AEMFNILZOJDQLW-QAGGRKNESA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:GHXKGEZOEBTGNZ-LLVKDONJSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:VQICTJVVFZCQCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:SMHXGVJSDWUGKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.3505
Molecular Formula:C21H16O2
InChIKey:HAKUEQCXTHCYOP-PGMHBOJBSA-N
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Compound Information
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:DIELDZAPFMXAHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.4776
Molecular Formula:C21H32O2
InChIKey:ORNBQBCIOKFOEO-QGVNFLHTSA-N
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Compound Information
Molecular Weight:281.3474
Molecular Formula:C15H23NO4
InChIKey:QVMNDCYDRSQEMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.9953
Molecular Formula:NNaO2
InChIKey:LPXPTNMVRIOKMN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:316.4345
Molecular Formula:C20H28O3
InChIKey:JYMVNNNTLDUEBG-PFIYWFKMSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:ZONYXWQDUYMKFB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:BGAXCPSNMHVHJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.4345
Molecular Formula:C20H28O3
InChIKey:GXOLMLOJBNSABS-XOJMLDNQSA-N
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Compound Information
Molecular Weight:302.3649
Molecular Formula:C18H22O4
InChIKey:JNVNUYOLMPAPCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:VHZDVXUZAAWPFF-JKSUJKDBSA-N
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Compound Information
Molecular Weight:208.2106
Molecular Formula:C11H12O4
InChIKey:ROMWRJNZSHFGEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:FKMCADCEOYUAFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2552
Molecular Formula:C15H12O
InChIKey:DQFBYFPFKXHELB-VAWYXSNFSA-N
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Compound Information
Molecular Weight:96.1034
Molecular Formula:C4H9NaO
InChIKey:MFRIHAYPQRLWNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:253.178
Molecular Formula:C9H9ArO4S
InChIKey:GFZMNOWEIQYSEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2387
Molecular Formula:C15H10O2
InChIKey:VHBFFQKBGNRLFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:ZBFFNPODXBJBPW-VIFPVBQESA-N
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Compound Information
Molecular Weight:62.134
Molecular Formula:C2H6S
InChIKey:QMMFVYPAHWMCMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.3296
Molecular Formula:C11H16OSi
InChIKey:AFFPCIMDERUIST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.124
Molecular Formula:C7H12ArNO
InChIKey:KIEMJUFGBOKSLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:LFSAPCRASZRSKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:392.1261
Molecular Formula:C13H14IO4P
InChIKey:NCPZLJHLIGVSKG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.2374
Molecular Formula:C9H17NO
InChIKey:JWUXJYZVKZKLTJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2225
Molecular Formula:C12H12O2
InChIKey:CBOWXFXOSFDESG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:317.3795
Molecular Formula:C18H23NO4
InChIKey:DJZOUOMUIDCPIF-IKGGRYGDSA-N
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Compound Information
Molecular Weight:392.209
Molecular Formula:C13H13IO4S
InChIKey:LRIUKPUCKCECPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:URLKBWYHVLBVBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.3241
Molecular Formula:C9H18OSi
InChIKey:SBEMOANGDSSPJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1204
Molecular Formula:C4H10O3
InChIKey:Not Available
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Compound Information
Molecular Weight:220.0567
Molecular Formula:C6CrO6
InChIKey:BTCPMXRIGSIGKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:NZZIMKJIVMHWJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.661
Molecular Formula:C10H13ClO3
InChIKey:CSUSWMYLSSMMDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:392.466
Molecular Formula:C20H24O6S
InChIKey:PREGKWNGRQMODU-MOXGXCLJSA-N
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:223.2252
Molecular Formula:C11H13NO4
InChIKey:YYULIDQKQKXJTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.0078
Molecular Formula:C6H5IO
InChIKey:Not Available
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Compound Information
Molecular Weight:254.2806
Molecular Formula:C16H14O3
InChIKey:BXCMWUUBPKZMDL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.4144
Molecular Formula:C24H20O2
InChIKey:HBJFDIOGYAKPFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.993
Molecular Formula:C2H3ArO
InChIKey:RYFPNOHYACPFTJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:VLKZOEOYAKHREP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:FHSAZOGISLHXPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:WZPYRYLJVNIBPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.992
Molecular Formula:C2H3ArO2
InChIKey:SNTTWLBHGRZWBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.355
Molecular Formula:C14H18O4S
InChIKey:HEBHNYQPRCQXTO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.3657
Molecular Formula:C13H18O3Si
InChIKey:VJLJBKXIFWDLNS-JLHYYAGUSA-N
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Compound Information
Molecular Weight:344.28
Molecular Formula:C15H16CrO6
InChIKey:ZAGNACOJYBZMIC-RQLHABPXSA-N
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Compound Information
Molecular Weight:172.34
Molecular Formula:C9H20OSi
InChIKey:PEHJULPJEVIIFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:442.266
Molecular Formula:C10H14F3IO4SSi
InChIKey:JXUVXOPAIYMOEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.1681
Molecular Formula:C10H8O4
InChIKey:LCDDKARXTUFJBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:GZVKEXBZZPWPBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.5454
Molecular Formula:C23H38O4
InChIKey:UDBHVRXYZJQGAW-CPDXTSBQSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:HVAMZGADVCBITI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.3325
Molecular Formula:C18H18O5
InChIKey:SKTAHPCCLORHHM-XBXARRHUSA-N
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Compound Information
Molecular Weight:262.2855
Molecular Formula:C18H15P
InChIKey:RIOQSEWOXXDEQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:473.3229
Molecular Formula:C23H22IO3
InChIKey:OWMMNPKQUGSOOO-VXKWHMMOSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.328
Molecular Formula:C13H16O5S
InChIKey:WVLIEBBSJBKUIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:348.4764
Molecular Formula:C21H32O4
InChIKey:JNHJGXQUDOYJAK-IYRCEVNGSA-N
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Compound Information
Molecular Weight:264.0173
Molecular Formula:C7H5IO3
InChIKey:AZJIXRYFAZOEMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:376.4004
Molecular Formula:C20H24O7
InChIKey:ZJKLOIKGUBBPNN-RBUKOAKNSA-N
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Compound Information
Molecular Weight:316.113
Molecular Formula:C7H9IO4S
InChIKey:WSUYPCBSGVAXNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.0762
Molecular Formula:C8H11IO2
InChIKey:SSTLWHMWDMWENH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:XHLHPRDBBAGVEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:322.0964
Molecular Formula:C10H11IO4
InChIKey:ZBIKORITPGTTGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.2347
Molecular Formula:C12H17O4P
InChIKey:HPEVTTNSIPGLEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.357
Molecular Formula:C9H14OSSi
InChIKey:GUPNOGNXUZRKJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.3166
Molecular Formula:C18H16O5
InChIKey:VSFZYCDPDWSYSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.3746
Molecular Formula:C16H25NO3
InChIKey:AMRZRFHNKPWEJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.3937
Molecular Formula:C24H21O6P
InChIKey:QSUXRAUUWRZSLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.3505
Molecular Formula:C21H16O2
InChIKey:SJMBKGWSQZFQRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.095
Molecular Formula:C3H8O
InChIKey:KFZMGEQAYNKOFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:JECYUBVRTQDVAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:AETKQQBRKSELEL-ZHACJKMWSA-N
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Compound Information
Molecular Weight:217.3068
Molecular Formula:C14H19NO
InChIKey:BIBARRYXKABQKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:365.2712
Molecular Formula:C18H22I
InChIKey:FGLZFXDJHLJUIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2485
Molecular Formula:C13H14O3
InChIKey:WUGVHYXLVLVPQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:LKTNAAYQZJAXCJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3172
Molecular Formula:C18H16O4
InChIKey:XILDZLMUGHIEKU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1739
Molecular Formula:C9H10O3
InChIKey:ITATYELQCJRCCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:CVBUKMMMRLOKQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.9952
Molecular Formula:H3O4P
InChIKey:NBIIXXVUZAFLBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ZWVHTXAYIKBMEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.5355
Molecular Formula:C15H25NO2Si2
InChIKey:ICLKYJOIYSSMFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.3177
Molecular Formula:C10H15NOSi
InChIKey:DUZISRJGZUUGJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2387
Molecular Formula:C15H10O2
InChIKey:NFBAXHOPROOJAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:348.287
Molecular Formula:C17H17O6P
InChIKey:ZEHLMHSANOBBHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.1183
Molecular Formula:C7H9O3P
InChIKey:KLFXGMZYFVBYAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:JEHHTJLQIHUCHN-HOCLYGCPSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.297
Molecular Formula:C16H16O2
InChIKey:PYPHPZOQIVEWHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.1505
Molecular Formula:C8H9F3O3
InChIKey:QGURUXBGLNKCPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.3507
Molecular Formula:C10H20OSi
InChIKey:IERTVMWHAUJPFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.184
Molecular Formula:C10H10O4
InChIKey:RCJLRLJUQFPODR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:RXAMIWOJDOJSTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.4144
Molecular Formula:C24H20O2
InChIKey:UDYCIDRROWQUHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.2366
Molecular Formula:C12H14O5
InChIKey:NHACGUARTMEQMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.3484
Molecular Formula:C18H20O5
InChIKey:DUWPDRCKCBMXIF-IAGOWNOFSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2704
Molecular Formula:C7H14O2Si
InChIKey:ROCZJWMPGISRQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:59.09
Molecular Formula:CHNS
InChIKey:GRHBQAYDJPGGLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.164
Molecular Formula:C5H5NOS
InChIKey:MOMFXATYAINJML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.237
Molecular Formula:C7H5F3O4S2
InChIKey:RATWEOPUFDQARS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:WPYMKLBDIGXBTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:BQQLUQRZQOODGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.232
Molecular Formula:C7H11NO3S
InChIKey:MGZFKDLPJBTOCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.2812
Molecular Formula:C16H14O2
InChIKey:SXXKUCVHZMMFIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:39.0123
Molecular Formula:H2NNa
InChIKey:ODZPKZBBUMBTMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:344.27
Molecular Formula:C20H17ArOP
InChIKey:JFFIEPLALIJFGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:504.3574
Molecular Formula:C24H25IO4
InChIKey:DHPKLROATGUWMV-GOTSBHOMSA-N
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Compound Information
Molecular Weight:55.971
Molecular Formula:ArH2N
InChIKey:RFPBURUTGOEBNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.2122
Molecular Formula:C13H10CrO4
InChIKey:BLQJRMOUXIIZHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:GHHYTRRAKDEMCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.44
Molecular Formula:C16H26O5S
InChIKey:IKZFNCFBJLKKDU-MLGOLLRUSA-N
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Compound Information
Molecular Weight:212.63
Molecular Formula:C10H9ClO3
InChIKey:FTUYTARZCNUSDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.254
Molecular Formula:C15H12O3
InChIKey:YEDFEBOUHSBQBT-GJZGRUSLSA-N
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Compound Information
Molecular Weight:170.593
Molecular Formula:C8H7ClO2
InChIKey:DMDCUPKBRHFLKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1483
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2161
Molecular Formula:C10H14O3
InChIKey:GHHYTRRAKDEMCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:CJNZAXGUTKBIHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:KPMKEVXVVHNIEY-RITPCOANSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:OZXHQHMTASSNBO-GJMOJQLCSA-N
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Compound Information
Molecular Weight:344.28
Molecular Formula:C15H16CrO6
InChIKey:ZAGNACOJYBZMIC-LUXIIRHWSA-N
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Compound Information
Molecular Weight:240.254
Molecular Formula:C15H12O3
InChIKey:YEDFEBOUHSBQBT-CABCVRRESA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2545
Molecular Formula:C7H12O2Si
InChIKey:Not Available
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Compound Information
Molecular Weight:162.997
Molecular Formula:ClCuO4
InChIKey:JTJVHKYOUOUOSL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:386.6535
Molecular Formula:C27H46O
InChIKey:PESKGJQREUXSRR-DMDXHKHNSA-N
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Compound Information
Molecular Weight:430.2051
Molecular Formula:C13H11F13O
InChIKey:VMOGNGJUZQWNAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:146.1427
Molecular Formula:C9H6O2
InChIKey:UHKAJLSKXBADFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:240.254
Molecular Formula:C15H12O3
InChIKey:OABFIJGAEVKMJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:322.3545
Molecular Formula:C20H18O4
InChIKey:UCSHIKBOKJMPQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:496.2541
Molecular Formula:C22H13IN2O4
InChIKey:OTVCFPYTBBQYAN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:OOVQCULARLASPF-DHZHZOJOSA-N
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Compound Information
Molecular Weight:190.1953
Molecular Formula:C11H10O3
InChIKey:NHIOAYPFYQRMFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.4611
Molecular Formula:C21H30O3
InChIKey:NKZLRJOJLCHNQR-NGFSFWIMSA-N
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Compound Information
Molecular Weight:278.39
Molecular Formula:C14H14O2S2
InChIKey:NANUPJPNOIZIPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.0318
Molecular Formula:C7H7F2I
InChIKey:ROJCSEAEQFJFGO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:SKCYVGUCBRYGTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.3235
Molecular Formula:C9H18O2Si
InChIKey:HRGSBMSQUFOZMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:354.1398
Molecular Formula:C14H11IO3
InChIKey:WWJSLXDTAVJVGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.4253
Molecular Formula:C14H24OSi
InChIKey:SDONODYDYLFMSG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:AIZCLPNQLZSCJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:210.2711
Molecular Formula:C15H14O
InChIKey:RDBAEHHVVNBKBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:DRLVMOAWNVOSPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:361.455
Molecular Formula:C19H23NO4S
InChIKey:ZZOGWLAXXKRQDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:222.273
Molecular Formula:P2S5
InChIKey:HWVAJUNEPOKXLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:NTPLXRHDUXRPNE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:580.5379
Molecular Formula:C29H41IO4
InChIKey:KXOKPTIVOMLOPC-FCWLDKDCSA-N
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Compound Information
Molecular Weight:361.1771
Molecular Formula:C16H12INO
InChIKey:LYPULBOGMMPRAG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.5102
Molecular Formula:C14H24O2Si2
InChIKey:SKIVMAWYJZAJHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2387
Molecular Formula:C15H10O2
InChIKey:OMUOMODZGKSORV-GXDHUFHOSA-N
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Compound Information
Molecular Weight:202.2491
Molecular Formula:C13H14O2
InChIKey:ICHMJHUCIOLELS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:470.1
Molecular Formula:C9H6F7IO4S
InChIKey:LAJPRPZAFDMWNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:404.6581
Molecular Formula:C24H40O3Si
InChIKey:KFTMRBPJHRYVOI-MIFDARQQSA-N
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Compound Information
Molecular Weight:244.716
Molecular Formula:C15H13ClO
InChIKey:KWONVZJFNURCKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:KGPCYWGHIZJCBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:285.3377
Molecular Formula:C17H19NO3
InChIKey:NSCPZUQVAKCWQG-QEJWPVCOSA-N
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Compound Information
Molecular Weight:544.341
Molecular Formula:C18H9Cl9
InChIKey:JDRHDKQKXPHNFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.811
Molecular Formula:C6H5BF5I
InChIKey:LRCLNEVSERJYJM-UHFFFAOYSA-N
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