Standard Article

Hydrogen-Bonding-Mediated Directed Osmium Dihydroxylation

  1. Timothy J. Donohoe,
  2. Carole J. R. Bataille,
  3. Paolo Innocenti

Published Online: 14 MAR 2012

DOI: 10.1002/0471264180.or076.01

Organic Reactions

Organic Reactions

How to Cite

Donohoe, T. J., Bataille, C. J. R. and Innocenti, P. 2012. Hydrogen-Bonding-Mediated Directed Osmium Dihydroxylation. Organic Reactions. 76:1:1–48.

Author Information

  1. University of Oxford, Chemistry Research Laboratory, Department of Chemistry, Oxford, OX1 3TA, UK

Publication History

  1. Published Online: 14 MAR 2012

Chemistry Terms

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Abstract

This chapter focuses on the dihydroxylation of alkenes using osmium tetraoxide that is directed by alcohols and amine derivatives through hydrogen bonding between the substrate and the oxidant. Discussion focuses on the different types of directing groups that are viable. The outcome from directed dehydroxylation of all the major classes of alkenes, including cyclic and acyclic substrates and varied alkene substration patterns, is also addressed. The mechanism section outlines the different reactivity patterns that various ligands can impart onto the osmium oxides together with the importance of chosing a solvent that encourages hydrogen bonding. The influence that the directing group has on syn selectivity is also discussed, in both the context of its position in space and with respect to the alkane, and the relationship between the PKa of the acidic proton and syn selectivity. Osmium tetraoxide has established itself as the reagent of choice for the syn-dihydroxylation of olefins, primarily because of its inertness towards other functional groups and lack of over-oxidation products. Information on research in regard to dihydroxylation is given. Only a few other synthetic methods are known that accomplish the direct addition of a diol unit across an alkene while controlling the stereochemical course of the process. The Woodward modification of the Prevost reaction (adds two oxygen atoms in a syn fashion across an alkane) is discussed in detail in the comparison of methods section.

Keywords:

  • Dihydroxylation;
  • Osmium tetroxide;
  • Mechanisms;
  • Site selectivity;
  • Conformational factors;
  • Hydrogen bonding;
  • Directing group;
  • Amines;
  • Alcohols;
  • Steric effects;
  • Method comparisons;
  • Sodium sulfite;
  • Acidic methanol;
  • Ethylenediamine;
  • Experimental procedures

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Compound Information
Molecular Weight:1.00794
Molecular Formula:H
InChIKey:GPRLSGONYQIRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:JJQXTSDYTYJQHK-HSUXUTPPSA-N
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Compound Information
Molecular Weight:706.9369
Molecular Formula:C40H54O9Si
InChIKey:XDUSUQYUUCUBBP-NLMPTFBQSA-N
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Compound Information
Molecular Weight:432.842
Molecular Formula:C16H28Cl3NO4Si
InChIKey:VESCVCDNIJPYNO-YNEHKIRRSA-N
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Compound Information
Molecular Weight:104.061
Molecular Formula:HNaO3S
InChIKey:DWAQJAXMDSEUJJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:183.2475
Molecular Formula:C10H17NO2
InChIKey:MZELDYOEBRPZKZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.33
Molecular Formula:C4H8O4Os
InChIKey:SOHKQZBXBBNRDV-NSHFDXEUSA-N
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Compound Information
Molecular Weight:326.33
Molecular Formula:C4H8O5Os
InChIKey:MRADSIUIVLBKHL-VVGVNYDESA-N
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Compound Information
Molecular Weight:304.189
Molecular Formula:C10H10F6N2O2
InChIKey:FRMLBZALLHNKDU-OLQVQODUSA-N
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Compound Information
Molecular Weight:244.3703
Molecular Formula:C14H28O3
InChIKey:DMHAQTOJPHMMLC-RDBSUJKOSA-N
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Compound Information
Molecular Weight:139.1949
Molecular Formula:C8H13NO
InChIKey:ZYVQVLHBHMJVEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.2386
Molecular Formula:C9H18O
InChIKey:AGJGJUGBPXOLEG-SOFGYWHQSA-N
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Compound Information
Molecular Weight:336.3796
Molecular Formula:C18H24O6
InChIKey:MLOGXROZZLAZPM-RCCFBDPRSA-N
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Compound Information
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:FDJKLIVKKYFLSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.3362
Molecular Formula:C14H24O7
InChIKey:HTTJXHDTBPJXFZ-RYMFRWLXSA-N
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Compound Information
Molecular Weight:359.352
Molecular Formula:C14H17NO8S
InChIKey:FVAHCIKCKOLSSU-ZBBUEOHVSA-N
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Compound Information
Molecular Weight:495.586
Molecular Formula:C24H33NO8S
InChIKey:QCMGATIZZNFISY-QWQGWLCTSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:NWVFBFHOQGKOIF-OLQVQODUSA-N
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Compound Information
Molecular Weight:202.2906
Molecular Formula:C11H22O3
InChIKey:YSTPDJIYAXVONL-ZYUZMQFOSA-N
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Compound Information
Molecular Weight:236.2191
Molecular Formula:C9H16O7
InChIKey:RRIDDKBZJHLFOJ-INWNABHMSA-N
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Compound Information
Molecular Weight:276.545
Molecular Formula:C8H12Cl3NO3
InChIKey:KRYBNVMQGMFFKJ-NGJCXOISSA-N
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Compound Information
Molecular Weight:213.1544
Molecular Formula:C7H10F3NO3
InChIKey:CKBOYJNWEHDCLV-MROZADKFSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:UPYRGSJVTFXYAC-MDZDMXLPSA-N
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Compound Information
Molecular Weight:376.618
Molecular Formula:C12H16Cl3NO6
InChIKey:YZSUOKAZQLUDSG-QXEWZRGKSA-N
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Compound Information
Molecular Weight:126.043
Molecular Formula:Na2O3S
InChIKey:GEHJYWRUCIMESM-UHFFFAOYSA-L
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:IGRLIBJHDBWKNA-SYDPRGILSA-N
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Compound Information
Molecular Weight:400.768
Molecular Formula:C17H28Cl3NO3
InChIKey:KMGCSOBAVVCGEL-YUOYJMCBSA-N
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Compound Information
Molecular Weight:285.359
Molecular Formula:C13H19NO4S
InChIKey:FMBNUECTYVNCAZ-FRRDWIJNSA-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:335.461
Molecular Formula:C18H25NO3S
InChIKey:WAIPUHDWYJQEHJ-BPQIPLTHSA-N
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Compound Information
Molecular Weight:316.3899
Molecular Formula:C16H28O6
InChIKey:PMVBTSZBFBXAKP-QLFBSQMISA-N
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Compound Information
Molecular Weight:258.2677
Molecular Formula:C12H18O6
InChIKey:SZEKSHIKGKBHIR-TUAOUCFPSA-N
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Compound Information
Molecular Weight:404.628
Molecular Formula:C13H16Cl3NO7
InChIKey:TZUCLYAZKUZKMX-YTWAJWBKSA-N
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Compound Information
Molecular Weight:378.4593
Molecular Formula:C21H30O6
InChIKey:SFDRDZAPYAVCQU-ACRUOGEOSA-N
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Compound Information
Molecular Weight:256.557
Molecular Formula:C9H12Cl3NO
InChIKey:YUNGPNFLLOOMQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:469.548
Molecular Formula:C22H31NO8S
InChIKey:PYRVIUAQQQVNBN-KJJMTIBFSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:ABZZOPIABWYXSN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.1628
Molecular Formula:C5H13NO
InChIKey:HMVFITKXZCNKSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.2772
Molecular Formula:C13H18O8
InChIKey:OTFIJXTWPQTDSF-MPZDIEGVSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:LRUBQXAKGXQBHA-FBXFSONDSA-N
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Compound Information
Molecular Weight:346.592
Molecular Formula:C11H14Cl3NO5
InChIKey:OMPOHCUVYINEEH-AYMMMOKOSA-N
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Compound Information
Molecular Weight:504.6985
Molecular Formula:C30H48O6
InChIKey:YKXMRIYGNPDEBJ-HJOGWXRNSA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:VRVSHOSUSHYQIQ-KXQHVCLCSA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:IZSANPWSFUSNMY-RFZPGFLSSA-N
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Compound Information
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:BTDLLJGRGRQELA-GJMOJQLCSA-N
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:PWBFTKWRAXFTLR-FXQIFTODSA-N
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Compound Information
Molecular Weight:187.259
Molecular Formula:C8H13NO2S
InChIKey:HRKPDBJMECLXCQ-CSMHCCOUSA-N
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Compound Information
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:SEEZWQHMVPAIBQ-NEPJUHHUSA-N
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Compound Information
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:QDTNILDFGVIQNQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.651
Molecular Formula:C12H20Cl3NO3
InChIKey:QESPUNPOQSBWJF-QCBRBAQYSA-N
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Compound Information
Molecular Weight:308.4895
Molecular Formula:C20H24OSi
InChIKey:KVYLWLIDFWYWJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:763.139
Molecular Formula:C36H66O11SSi2
InChIKey:VQOWYXDBJVUFET-NZCKOERASA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:VTDKJKUKALZPAM-FPFOFBBKSA-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:404.4966
Molecular Formula:C23H32O6
InChIKey:IABSYWJWIJHHAI-DCCLSMNISA-N
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Compound Information
Molecular Weight:256.557
Molecular Formula:C9H12Cl3NO
InChIKey:RYQBMHTYJIITDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.571
Molecular Formula:C9H14Cl3NO3
InChIKey:ZLHKASXVYQJHIK-QYNIQEEDSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:Not Available
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Compound Information
Molecular Weight:205.049
Molecular Formula:C7H9BrO2
InChIKey:VPNVRQSCXRUHNP-NKWVEPMBSA-N
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Compound Information
Molecular Weight:253.3804
Molecular Formula:C15H27NO2
InChIKey:ZJSIDQOOAXJARP-XSCHDIRWSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:WEIMJSIRDZDHAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2533
Molecular Formula:C9H20O3
InChIKey:DPVQZMWZCACCBA-IWSPIJDZSA-N
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Compound Information
Molecular Weight:512.5327
Molecular Formula:C31H29O5P
InChIKey:COYHTYLJOKPOAT-WZKMZYQSSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:DSWQLIBPWWTIIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:CWOYCUJWPHFCLB-DSYKOEDSSA-N
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Compound Information
Molecular Weight:286.3209
Molecular Formula:C14H22O6
InChIKey:CPCFTIMNOFZSGA-QSWPVVRKSA-N
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Compound Information
Molecular Weight:242.53
Molecular Formula:C8H10Cl3NO
InChIKey:XMYWNYUVLYYMMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:418.816
Molecular Formula:C15H26Cl3NO4Si
InChIKey:KOGDAUQVBYTDSF-QJPTWQEYSA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:ZHMPXIDAUXCKIQ-JKUQZMGJSA-N
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Compound Information
Molecular Weight:190.107
Molecular Formula:Na2O5S2
InChIKey:LDTLADDKFLAYJA-UHFFFAOYSA-L
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Compound Information
Molecular Weight:142.218
Molecular Formula:C8H19Al
InChIKey:AZWXAPCAJCYGIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2045
Molecular Formula:C9H14O5
InChIKey:SOBLFJXPOUTECV-XLPZGREQSA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:VQWAZBMRMSMLPG-CRCLSJGQSA-N
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Compound Information
Molecular Weight:388.79
Molecular Formula:C14H24Cl3NO3Si
InChIKey:BSVOUTUISUXETR-MNOVXSKESA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:IUGYQRQAERSCNH-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:199.2038
Molecular Formula:C9H13NO4
InChIKey:JQLFODPEIMBALS-ANLVUFKYSA-N
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Compound Information
Molecular Weight:302.3633
Molecular Formula:C15H26O6
InChIKey:CXUZNXINUJALNZ-RBSFLKMASA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:YDRSQRPHLBEPTP-OLQVQODUSA-N
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Compound Information
Molecular Weight:240.1923
Molecular Formula:C11H13O4P
InChIKey:LNTOUAVPLDMCOV-XZBSXTPXSA-N
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Compound Information
Molecular Weight:111.1848
Molecular Formula:C7H13N
InChIKey:SBYHFKPVCBCYGV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:OOEPVZSVTNDRRX-BDAKNGLRSA-N
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Compound Information
Molecular Weight:222.1926
Molecular Formula:C8H14O7
InChIKey:DCXMXXNUXSBWDI-ZWGHOWJVSA-N
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Compound Information
Molecular Weight:606.5703
Molecular Formula:C26H38O16
InChIKey:MQDROXROKAOHHY-DCIGHTRJSA-N
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Compound Information
Molecular Weight:326.3432
Molecular Formula:C19H18O5
InChIKey:FRJJTGQOODAMLX-YCEFEEMOSA-N
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Compound Information
Molecular Weight:307.451
Molecular Formula:C17H25NO2S
InChIKey:GKJYTPDMKNFZBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.1235
Molecular Formula:C6H8O7
InChIKey:KRKNYBCHXYNGOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.3285
Molecular Formula:C19H16O3
InChIKey:NRCDSMSTCBEDAT-KUHUBIRLSA-N
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Compound Information
Molecular Weight:225.037
Molecular Formula:C6H9BrO4
InChIKey:AGYFAAMKMRARQB-BGPJRJDNSA-N
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Compound Information
Molecular Weight:193.1663
Molecular Formula:C8H10F3NO
InChIKey:BRUZPHLIKWLQMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:344.5185
Molecular Formula:C17H32O5Si
InChIKey:HPMCJILMTVJJEO-MGPQQGTHSA-N
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Compound Information
Molecular Weight:134.1305
Molecular Formula:C5H10O4
InChIKey:KZVAAIRBJJYZOW-UOWFLXDJSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:GLZPCOQZEFWAFX-JXMROGBWSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:ORRPKMFHDILRKR-LPEHRKFASA-N
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Compound Information
Molecular Weight:402.917
Molecular Formula:C10H10Cl6N2O2
InChIKey:UBJYMEJMUAQBGQ-OLQVQODUSA-N
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Compound Information
Molecular Weight:395.5668
Molecular Formula:C23H29NO3Si
InChIKey:IOXMSQQYOOSDRT-UZUQRXQVSA-N
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Compound Information
Molecular Weight:544.687
Molecular Formula:C24H36O10SSi
InChIKey:JCZMOKCGWVEDJC-JLMDMGSGSA-N
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Compound Information
Molecular Weight:298.636
Molecular Formula:C12H18Cl3NO
InChIKey:ZBEHNKYBJHWDRQ-BDAKNGLRSA-N
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Compound Information
Molecular Weight:325.2809
Molecular Formula:C13H18F3NO5
InChIKey:FUYAVYPNGRGWNX-HOSYDEDBSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:BVOSSZSHBZQJOI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.2386
Molecular Formula:C9H18O
InChIKey:PNLIZTGZMGUPNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:349.41
Molecular Formula:C7H13NO3Os
InChIKey:SPZMZTQZNTZTEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.023
Molecular Formula:C6H7BrO2
InChIKey:KLPGXZKAVBGFGF-NTSWFWBYSA-N
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Compound Information
Molecular Weight:290.571
Molecular Formula:C9H14Cl3NO3
InChIKey:KQVOMODCEAEWHR-GKROBHDKSA-N
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Compound Information
Molecular Weight:134.1305
Molecular Formula:C5H10O4
InChIKey:DNVIZCLYSNCBKS-VERZDPOYSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:IXRKVYPZVKLYJV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:366.753
Molecular Formula:C17H26Cl3NO
InChIKey:ZUEUURZYMKXMND-SDNWHVSQSA-N
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Compound Information
Molecular Weight:274.207
Molecular Formula:C11H15O6P
InChIKey:ITRDJKVXZGVVHU-YYFWFECFSA-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:330.635
Molecular Formula:C12H18Cl3NO3
InChIKey:YLMNWWPLRYJBSQ-DGPDRUAKSA-N
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Compound Information
Molecular Weight:678.92
Molecular Formula:C26H40N2O5OsSi
InChIKey:UINIDEMVSFIRDH-MGMMIZOZSA-N
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Compound Information
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:MVHTVXFDPMHZNE-ZXFHETKHSA-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:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:311.2543
Molecular Formula:C12H16F3NO5
InChIKey:ZJRCARGHZNQTLN-KXUCPTDWSA-N
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Compound Information
Molecular Weight:332.651
Molecular Formula:C12H20Cl3NO3
InChIKey:SKGCKIPKAWDPKV-UYXSQOIJSA-N
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Compound Information
Molecular Weight:488.4823
Molecular Formula:C22H32O12
InChIKey:HZRVKSLVRMZCGD-NBWOUMIXSA-N
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Compound Information
Molecular Weight:316.3038
Molecular Formula:C14H20O8
InChIKey:MCRKABDCFOWPHD-LVEBTZEWSA-N
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Compound Information
Molecular Weight:740.9515
Molecular Formula:C40H56O11Si
InChIKey:KAADDHNXDSWUSN-KSEIOZTKSA-N
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Compound Information
Molecular Weight:89.1362
Molecular Formula:C4H11NO
InChIKey:UEEJHVSXFDXPFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.545
Molecular Formula:C8H12Cl3NO3
InChIKey:CLMMVHLVUMUKEF-NGJCXOISSA-N
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Compound Information
Molecular Weight:494.912
Molecular Formula:C21H30Cl3NO4Si
InChIKey:BHBLZSJTJRCZRB-BZSNNMDCSA-N
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Compound Information
Molecular Weight:95.121
Molecular Formula:CH5NO2S
InChIKey:HNQIVZYLYMDVSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:721.83
Molecular Formula:C27H37N3O8Os
InChIKey:TZGHDGSBWVTXPY-UTDGTWKHSA-N
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Compound Information
Molecular Weight:344.357
Molecular Formula:C16H24O8
InChIKey:VWKLDHUVYDVYOF-LQKXBSAESA-N
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Compound Information
Molecular Weight:244.3703
Molecular Formula:C14H28O3
InChIKey:JHOIBGMZFSTDQN-HRFIDBLHSA-N
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Compound Information
Molecular Weight:314.374
Molecular Formula:C16H26O6
InChIKey:LDVZNDOJCLLZFM-HZPDHXFCSA-N
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Compound Information
Molecular Weight:166.9122
Molecular Formula:C2H3AgO2
InChIKey:CQLFBEKRDQMJLZ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:GAWOXNZNAZBOET-KXQHVCLCSA-N
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Compound Information
Molecular Weight:207.1929
Molecular Formula:C9H12F3NO
InChIKey:OCMPYMWRYHCKFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:325.337
Molecular Formula:C14H15NO6S
InChIKey:DSGARXOOJDIRJJ-KTYPHDMWSA-N
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Compound Information
Molecular Weight:179.1397
Molecular Formula:C7H8F3NO
InChIKey:YBLARTYDUQXAPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:370.4819
Molecular Formula:C23H30O4
InChIKey:KVPIPZBCEOKHQX-PTRTWWQBSA-N
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Compound Information
Molecular Weight:309.424
Molecular Formula:C16H23NO3S
InChIKey:BJDJBDKFDIRWNX-HOTGVXAUSA-N
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Compound Information
Molecular Weight:494.912
Molecular Formula:C21H30Cl3NO4Si
InChIKey:FCEOSBHSHNFAIT-KURKYZTESA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:CDOSHBSSFJOMGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.0339
Molecular Formula:KMnO4
InChIKey:VZJVWSHVAAUDKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.181
Molecular Formula:C8H12F3NO3
InChIKey:JWLFJEOWKKZFLI-NGJCXOISSA-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:247.2881
Molecular Formula:C11H21NO5
InChIKey:YRVXAZBFLWGCSO-HLTSFMKQSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:WWLAVOQIMXATHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:429.5814
Molecular Formula:C23H31NO5Si
InChIKey:PJQLXAGYFZEYEX-PDIWNELESA-N
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Compound Information
Molecular Weight:228.504
Molecular Formula:C7H8Cl3NO
InChIKey:FEIYSQNVUBQDMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.53
Molecular Formula:C8H10Cl3NO
InChIKey:FVOHBENPTIIWPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.518
Molecular Formula:C7H10Cl3NO3
InChIKey:NJFYVFSIVDARHW-MROZADKFSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:AAUZPDAUBFXASQ-UWVGGRQHSA-N
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Compound Information
Molecular Weight:481.559
Molecular Formula:C23H31NO8S
InChIKey:PDVOPQXQBBAWNJ-QCBQRGATSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:KWLYWDDDUFOSOY-SPJNRGJMSA-N
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Compound Information
Molecular Weight:378.5332
Molecular Formula:C17H34O7Si
InChIKey:HLIXRKQKMDOIAH-IKOXMDCHSA-N
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Compound Information
Molecular Weight:466.857
Molecular Formula:C16H30Cl3NO6Si
InChIKey:YKFAAVIEHWHXOE-NJMOYASZSA-N
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Compound Information
Molecular Weight:362.591
Molecular Formula:C11H14Cl3NO6
InChIKey:JFDRVAQBBCPSGL-XHNCKOQMSA-N
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Compound Information
Molecular Weight:286.54
Molecular Formula:C9H10Cl3NO3
InChIKey:WELZVQMAPCKCAY-RITPCOANSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:MEIRRNXMZYDVDW-MQQKCMAXSA-N
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Compound Information
Molecular Weight:221.274
Molecular Formula:C8H15NO4S
InChIKey:ZKSHDMDADDCVIA-JAJWTYFOSA-N
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Compound Information
Molecular Weight:434.654
Molecular Formula:C14H18Cl3NO8
InChIKey:PJTBACPWYYHGFO-WHOHXGKFSA-N
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Compound Information
Molecular Weight:260.3713
Molecular Formula:C17H24O2
InChIKey:DLRMRQMTMPSNDS-HOFZKYPUSA-N
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Compound Information
Molecular Weight:239.064
Molecular Formula:C7H11BrO4
InChIKey:GVCDFTBFBPWEEX-ZTYPAOSTSA-N
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Compound Information
Molecular Weight:422.804
Molecular Formula:C14H26Cl3NO5Si
InChIKey:OZBYOFSZUBKMJO-ZRUFSTJUSA-N
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Compound Information
Molecular Weight:213.8918
Molecular Formula:INaO4
InChIKey:JQWHASGSAFIOCM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:445.5479
Molecular Formula:C21H30F3NO4Si
InChIKey:QZBMYXADLLCPBI-BZSNNMDCSA-N
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Compound Information
Molecular Weight:314.374
Molecular Formula:C16H26O6
InChIKey:QJCRDZYWTXAZDN-ZBFHGGJFSA-N
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Compound Information
Molecular Weight:60.1182
Molecular Formula:C3H9N
InChIKey:GETQZCLCWQTVFV-UHFFFAOYSA-O
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Compound Information
Molecular Weight:666.8007
Molecular Formula:C44H42O6
InChIKey:LKNNCZGQSCNZAY-GLGKVNTQSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:UCRUYCZYIBQXMV-LDCOFTPGSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:XEKOWRVHYACXOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:PBVCXULABJAIMG-ZJUUUORDSA-N
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Compound Information
Molecular Weight:263.235
Molecular Formula:C7H12F3NO4S
InChIKey:QRGITHXHKPNOIO-NGJCXOISSA-N
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Compound Information
Molecular Weight:521.005
Molecular Formula:C14H16Cl6N2O6
InChIKey:KEAQFUYANUCZOP-FIRGSJFUSA-N
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Compound Information
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:KWYHDKDOAIKMQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.0983
Molecular Formula:C2H8N2
InChIKey:PIICEJLVQHRZGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:528.926
Molecular Formula:C21H32Cl3NO6Si
InChIKey:XEWFTSDLFAPYLU-FPSMNIFISA-N
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Compound Information
Molecular Weight:213.2735
Molecular Formula:C11H19NO3
InChIKey:WMSAKHSFKKKXPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.345
Molecular Formula:C13H17NO2S
InChIKey:UIXHIGQCEVVUAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:778.9802
Molecular Formula:C48H54N6O4
InChIKey:YUCBLVFHJWOYDN-HCSLULSMSA-N
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Compound Information
Molecular Weight:452.83
Molecular Formula:C15H28Cl3NO6Si
InChIKey:PFQGGMMLDHNLDX-PZWNZHSQSA-N
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Compound Information
Molecular Weight:228.504
Molecular Formula:C7H8Cl3NO
InChIKey:XKHXURGGOJEQNQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:363.4049
Molecular Formula:C19H25NO6
InChIKey:MAYXMRWIIGOAGB-BZUAXINKSA-N
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Compound Information
Molecular Weight:130.2312
Molecular Formula:C7H18N2
InChIKey:DMQSHEKGGUOYJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.451
Molecular Formula:C20H30O2
InChIKey:VGIPTEZZZVOSOA-VHUCWBOISA-N
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Compound Information
Molecular Weight:304.2329
Molecular Formula:C12H17O7P
InChIKey:LZOZRXVSJUWAKG-QWZVGXRLSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.544
Molecular Formula:C8H12Cl3NO4
InChIKey:KVMLNJUSVBLBHX-KZLJYQGOSA-N
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Compound Information
Molecular Weight:256.557
Molecular Formula:C9H12Cl3NO
InChIKey:SQTUITRGXIONNT-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:332.3032
Molecular Formula:C14H20O9
InChIKey:ULWHEXUWXLOVPV-RQJABVFESA-N
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Compound Information
Molecular Weight:274.2671
Molecular Formula:C12H18O7
InChIKey:IHGKPANOXKCONC-IJLUTSLNSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:FBAPOIPDUVYEKZ-SOFGYWHQSA-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:384.562
Molecular Formula:C18H28O5SSi
InChIKey:YDGVCIIXXHHJPY-BBWFWOEESA-N
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Compound Information
Molecular Weight:540.776
Molecular Formula:C21H24Cl3NO9
InChIKey:RADXJUNBQFWCQR-SPOLIRPYSA-N
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Compound Information
Molecular Weight:330.635
Molecular Formula:C12H18Cl3NO3
InChIKey:GMULAUIRIGUVBV-SNZBGZMYSA-N
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Compound Information
Molecular Weight:422.2771
Molecular Formula:C14H16F6N2O6
InChIKey:BHEFWFSKJSHYGH-FIRGSJFUSA-N
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Compound Information
Molecular Weight:46.0254
Molecular Formula:CH2O2
InChIKey:BDAGIHXWWSANSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.2411
Molecular Formula:C11H16O6
InChIKey:ICRGFXAHKXBCFQ-JGPRNRPPSA-N
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Compound Information
Molecular Weight:360.618
Molecular Formula:C12H16Cl3NO5
InChIKey:WQOKBMZJNWTBLA-KXUCPTDWSA-N
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Compound Information
Molecular Weight:320.554
Molecular Formula:C9H12Cl3NO5
InChIKey:CJEOGDMCIMZGIT-BGPJRJDNSA-N
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Compound Information
Molecular Weight:244.503
Molecular Formula:C7H8Cl3NO2
InChIKey:CVRAKTDGPVZXDX-CRCLSJGQSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.3556
Molecular Formula:C14H26O
InChIKey:SFLDMIAWWFMKJZ-ACCUITESSA-N
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Compound Information
Molecular Weight:632.786
Molecular Formula:C44H40O4
InChIKey:KBYIBVQHTVVRSF-ODIZAFFMSA-N
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Compound Information
Molecular Weight:75.1097
Molecular Formula:C3H9NO
InChIKey:Not Available
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Compound Information
Molecular Weight:258.53
Molecular Formula:C8H10Cl3NO2
InChIKey:IOAMVAJQWYVSPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:351.3957
Molecular Formula:C21H21NO4
InChIKey:HJAUMQYSIPKKDM-LWYYNNOASA-N
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Compound Information
Molecular Weight:233.2185
Molecular Formula:C9H15NO6
InChIKey:CMEJUZHCJMKVJM-NGESMGFYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:TXPJSTNMZHBTRF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.374
Molecular Formula:C16H26O6
InChIKey:HEODUNZSUWVQSY-PKNBQFBNSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:DBZFJCXQJLIGCS-CMDGGOBGSA-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:464.68
Molecular Formula:C15H20Cl3NO9
InChIKey:LNSVUPNOQYJLRX-NJMOYASZSA-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:260.2405
Molecular Formula:C11H16O7
InChIKey:AGTSQJAVJCFOSJ-MXWKQRLJSA-N
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Compound Information
Molecular Weight:318.625
Molecular Formula:C11H18Cl3NO3
InChIKey:WILMTFIIYXXYAM-XSSZXYGBSA-N
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Compound Information
Molecular Weight:301.52
Molecular Formula:C14H27NO2SSi
InChIKey:DORDWMZKAQOYNW-AGIUHOORSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:PSBABBDEUFNFKJ-YFKPBYRVSA-N
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Compound Information
Molecular Weight:715.719
Molecular Formula:C31H41NO16S
InChIKey:AYJXKFITBRZMQZ-RNEGTYQJSA-N
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Compound Information
Molecular Weight:296.621
Molecular Formula:C12H16Cl3NO
InChIKey:PCJWTDNPZWBEKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2533
Molecular Formula:C9H20O3
InChIKey:XUMVHVIMLGBULT-SFYZADRCSA-N
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Compound Information
Molecular Weight:252.3493
Molecular Formula:C15H24O3
InChIKey:CIZWYOSBCQWFQY-QLFBSQMISA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:HSZAOCQIVDVCSS-UWVGGRQHSA-N
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Compound Information
Molecular Weight:335.535
Molecular Formula:C14H29NO4SSi
InChIKey:PZQVONWORHBJHY-IEECTRCBSA-N
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Compound Information
Molecular Weight:102.1781
Molecular Formula:C5H14N2
InChIKey:VGIVLIHKENZQHQ-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:302.3633
Molecular Formula:C15H26O6
InChIKey:RLOAPXMZGSEIMK-FICVDOATSA-N
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Compound Information
Molecular Weight:207.43
Molecular Formula:Cl3Ru
InChIKey:RVSOQSOUWJXKOX-UHFFFAOYSA-K
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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:142.2386
Molecular Formula:C9H18O
InChIKey:HZYRZLVSSYYSDP-SREVYHEPSA-N
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Compound Information
Molecular Weight:397.4196
Molecular Formula:C19H27NO8
InChIKey:NZEKTUNQJFWENQ-OLMNGRFOSA-N
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Compound Information
Molecular Weight:298.636
Molecular Formula:C12H18Cl3NO
InChIKey:WFLZMDOXSDOVDO-NXEZZACHSA-N
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Compound Information
Molecular Weight:219.3657
Molecular Formula:C15H25N
InChIKey:ZOXCSZIWGYKIPP-CABCVRRESA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:PCZLKMKSZJBMQF-SRVKXCTJSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:ZYFOXJIPDLNGDK-IUCAKERBSA-N
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Compound Information
Molecular Weight:258.53
Molecular Formula:C8H10Cl3NO2
InChIKey:DNISEUQNZRMJNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.3713
Molecular Formula:C17H24O2
InChIKey:FPORRLNDIKOZSF-VAWYXSNFSA-N
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Compound Information
Molecular Weight:329.244
Molecular Formula:C6FeK3N6
InChIKey:BYGOPQKDHGXNCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.279
Molecular Formula:C13H18O5
InChIKey:BSEAGNYRUYZOTA-JHJVBQTASA-N
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Compound Information
Molecular Weight:117.1463
Molecular Formula:C5H11NO2
InChIKey:LFTLOKWAGJYHHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.23
Molecular Formula:O4Os
InChIKey:Not Available
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Compound Information
Molecular Weight:229.22
Molecular Formula:C7H10F3NO2S
InChIKey:DXEDEYWYXZRFQL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:374.645
Molecular Formula:C13H18Cl3NO5
InChIKey:WUQBSJRFZSODSR-OUAUKWLOSA-N
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Compound Information
Molecular Weight:462.6188
Molecular Formula:C27H42O6
InChIKey:OKQOYVRGBHDCIE-PWRODBHTSA-N
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Compound Information
Molecular Weight:244.503
Molecular Formula:C7H8Cl3NO2
InChIKey:QCKBPPFUPWUFBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.24
Molecular Formula:H2O4Os
InChIKey:SCGAMWZSARVLOE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:491.4118
Molecular Formula:C21H24F3NO9
InChIKey:OGIIPCWSNFOQBY-SPOLIRPYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:CNTQWODJJQFZLR-NTSWFWBYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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