Standard Article

The Catalyzed α-Hydroxyalkylation and α-Aminoalkylation of Activated Olefins (The Morita—Baylis—Hillman Reaction)

  1. Engelbert Ciganek

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or051.02

Organic Reactions

Organic Reactions

How to Cite

Ciganek, E. 2004. The Catalyzed α-Hydroxyalkylation and α-Aminoalkylation of Activated Olefins (The Morita—Baylis—Hillman Reaction). Organic Reactions. 51:2:201–350.

Author Information

  1. Kennett Square, Pennsylvania

Publication History

  1. Published Online: 15 APR 2004

Chemistry Terms

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Abstract

In a patent application published in 1972, Baylis and Hillman reported the reaction of acetaldehyde with ethyl acrylate and acrylonitrile in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane to give the α-hydroxyethylated products in good yields. No structure proof was given. The assignment eventually was shown to be correct, but since the initial disclosure was not followed by a journal publication, this remarkably simple, atom-efficient, and useful reaction was ignored for a number of years, and it has been only fairly recently that its potential has begun to be explored. The transformation is now commonly referred to as the Baylis–Hillman reaction. This is unfortunate because credit for its invention clearly belongs to Morita, who five years earlier, in patents and a brief paper reported the same reaction with the exception that tertiary phosphines were used as the catalysts; he also proposed the currently accepted mechanism. Baylis and Hillman made reference to Morita's work in their patent application. It is true that tertiary amines in general are cheaper, less toxic, and more readily removed than tertiary phosphines. However, the latter sometimes give higher yields in shorter reaction times, and there are a number of examples where they are the only useful catalysts.

The DABCO-catalyzed reaction is slow, and reaction times at room temperature of days or even weeks are common. Attempts to remedy this situation by use of other amine catalysts, change of reaction temperature, high pressure, or microwave irradiation have been partially successful. Activated olefins other than acrylonitrile and acrylic esters that have now been shown to undergo the reaction include α,β-unsaturated aldehydes and ketones, vinyl sulfoxides, vinyl sulfones, vinylsulfonates, and vinylphosphonates. β-Substituted activated olefins do not normally react. Among electrophiles other than aldehydes, unactivated ketones undergo the Morita–Baylis–Hillman reaction only under high pressure, but activation such as in α-halo ketones, α-keto esters, α-keto lactones, and nonenolizable α-diketones often produces very reactive substrates. Imines also can be employed, provided they carry a sufficiently electronegative group on nitrogen.

This chapter covers catalyzed α-hydroxyalkylations and α-aminoalkylations of activated olefins. Transition metal catalyzed reactions of this type, are also included even though they proceed by a different mechanism. Transformations that require stoichiometric amounts of reagents or more than one step are summarized in the section on Comparison With Other Methods but are not included in the Tabular Survey. The Morita–Baylis–Hillman reaction has been reviewed before.

Keywords:

  • catalysts;
  • hydroxyalklyation;
  • aminoalkylation;
  • activated olefin;
  • acrylates;
  • allenic esters;
  • acrylamides;
  • acrylonitrile;
  • acrolein;
  • unsaturated ketones;
  • vinyl sulfoxides;
  • vinyl sulfones;
  • vinylsulfonates;
  • vinylphosphonates;
  • substituted activated olefins;
  • electrophile;
  • intramolecular reactions;
  • side reactions;
  • aldehydes;
  • diketones;
  • keto esters;
  • keto lactones;
  • imines;
  • iminium salts;
  • Aldol and Michael reactions;
  • Morita-Baylis-Hillman reaction;
  • comparison of methods;
  • synthetic utility;
  • experimental conditions;
  • experimental procedures;
  • tabular survey

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:CQEYYJKEWSMYFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.35
Molecular Formula:C20H23LiN2O2
InChIKey:JJWIMFIAYUMNAK-VJAUXQICSA-N
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Compound Information
Molecular Weight:290.3111
Molecular Formula:C16H18O5
InChIKey:QGJFPKHRCHOLFZ-ABLWVSNPSA-N
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Compound Information
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:UDSUCEZOEPVETD-HFLPBZFISA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.231
Molecular Formula:C10H16O5
InChIKey:MDBWODYZTISSKP-HTQZYQBOSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:NBBJYMSMWIIQGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.307
Molecular Formula:C11H15NO2S
InChIKey:LTLUFWJKMDDMIJ-XFXZXTDPSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:QRMVLKSYNCXYKV-FNORWQNLSA-N
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Compound Information
Molecular Weight:289.2833
Molecular Formula:C15H15NO5
InChIKey:GSMGDWVEWHQGEG-SKDRFNHKSA-N
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Compound Information
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:QKKVAZVSTINTRA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:YXXJWGRPRXGYLA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.4498
Molecular Formula:C20H30O4
InChIKey:INFAORRZXMTJSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:UYVXCTUUBBNTTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2203
Molecular Formula:C9H16O5
InChIKey:PXVMFUIMDOJSQF-HTQZYQBOSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:REFRKUNIVJSIMQ-VXNVDRBHSA-N
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Compound Information
Molecular Weight:202.2045
Molecular Formula:C9H14O5
InChIKey:OQOCQBJWOCRPQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:HGBOYTHUEUWSSQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:YHRYIGKHZVPXAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.1941
Molecular Formula:C11H9NO3
InChIKey:HAFHCXUQAOHMMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.006
Molecular Formula:C5H6Cl2O2
InChIKey:DWBXLPVFYFOPIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1491
Molecular Formula:C9H7FO2
InChIKey:QVQUMFLLXDVPJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.3065
Molecular Formula:C17H16O4
InChIKey:YDMCUZANYFQNIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:WXZUVXFBEAOGOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.4504
Molecular Formula:C20H30O3
InChIKey:OYYLUHLGYVIQNX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:WPGCVJMESABHTO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:315.3621
Molecular Formula:C15H25NO6
InChIKey:MDGJAPMWSVGXHY-GHMZBOCLSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:WFJNXICXEHGDLB-UHFFFAOYSA-N
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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:284.3065
Molecular Formula:C17H16O4
InChIKey:CNVIBLGYVAYGCH-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:250.2903
Molecular Formula:C14H18O4
InChIKey:IISXOVNDNFDDEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.2897
Molecular Formula:C14H21OP
InChIKey:NKAHLKJKYXHCFT-MRXNPFEDSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:SJNALLRHIVGIBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.1743
Molecular Formula:C11H8CrO5
InChIKey:GXZQPDZDIYKRBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.2806
Molecular Formula:C16H14O3
InChIKey:OGTJZBXJYPDZPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.271
Molecular Formula:C16H13FO3
InChIKey:WVYOASAMCXOSAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:QZPSOSOOLFHYRR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:OEQRZPWMXXJEKU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:ISXSCDLOGDJUNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1249
Molecular Formula:C3H10N2
InChIKey:XFNJVJPLKCPIBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.388
Molecular Formula:C2HCl3O
InChIKey:HFFLGKNGCAIQMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:GQHTUMJGOHRCHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:KSMVZQYAVGTKIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2378
Molecular Formula:C12H14O3
InChIKey:KOCVRYUTPIQIEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:RXNOQIWGGFWNOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2372
Molecular Formula:C12H14O4
InChIKey:NFFIYJOSRGRDPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:297.3484
Molecular Formula:C18H19NO3
InChIKey:OOEHXKKZNWMDOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:HFGYAXCVTHXUQC-PHDIDXHHSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZTQSAGDEMFDKMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:ICMBTQSRUNSRKI-ZETCQYMHSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:DCVYJILSQVNHOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:30.026
Molecular Formula:CH2O
InChIKey:Not Available
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Compound Information
Molecular Weight:1152.23
Molecular Formula:C72H62P4Ru
InChIKey:SORUBCSKZRCDPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2372
Molecular Formula:C12H14O4
InChIKey:ZMEQVFFDSOLGBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:311.397
Molecular Formula:C15H21NO4S
InChIKey:VCFNMRSJAGQNCL-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:44.0526
Molecular Formula:C2H4O
InChIKey:IKHGUXGNUITLKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:NCJGJDNWSHATQH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:Not Available
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:VZGOKIHNKHAORQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:FCJJZKCJURDYNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.3285
Molecular Formula:C13H24O2
InChIKey:FWLDHHJLVGRRHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:JECYIVDZYGGHOH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.3279
Molecular Formula:C13H24O3
InChIKey:IQEWHTMQTSAPLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.2264
Molecular Formula:C11H13NO2
InChIKey:VDHMFBVEJUXEOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.1949
Molecular Formula:C8H13NO
InChIKey:MKKHZSTVOVZMCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:KMRMUZKLFIEVAO-IUCAKERBSA-N
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Compound Information
Molecular Weight:272.271
Molecular Formula:C16H13FO3
InChIKey:MWHLVHPXNAONGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:MLUCVPSAIODCQM-NSCUHMNNSA-N
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Compound Information
Molecular Weight:269.36
Molecular Formula:C13H19NO3S
InChIKey:QYWKUFBZHFLMBU-KWBADKCTSA-N
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Compound Information
Molecular Weight:259.2988
Molecular Formula:C12H21NO5
InChIKey:JUBPNAGDMOAOGG-BDAKNGLRSA-N
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Compound Information
Molecular Weight:290.3972
Molecular Formula:C18H26O3
InChIKey:BLSISORVVATUDG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.2729
Molecular Formula:C11H19NO4
InChIKey:PNJXYVJNOCLJLJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3071
Molecular Formula:C17H16O3
InChIKey:MHXWSGZCQVSALU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.4028
Molecular Formula:C20H24O3
InChIKey:YUTTXDJZXIOSHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2111
Molecular Formula:C11H11NO
InChIKey:KWHCFQDPVYYUNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.573
Molecular Formula:C12H11Cl3O3
InChIKey:PLNNCFQATSQGRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:LNMQRPPRQDGUDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:OCIFJWVZZUDMRL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:JWKATEVIPLVOBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:BHJLNKFYANWDOM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.3278
Molecular Formula:C13H23NO
InChIKey:XTZREJZBFIXMJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:YSGPYVWACGYQDJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:322.2785
Molecular Formula:C17H13F3O3
InChIKey:WEHVUALOMZWYPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:LBBCKLBUFAQQQA-DJWKRKHSSA-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:114.1424
Molecular Formula:C6H10O2
InChIKey:PNXMTCDJUBJHQJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.498
Molecular Formula:C2H3ClO
InChIKey:WETWJCDKMRHUPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:HOLIWIAOUNQYRC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1648
Molecular Formula:C6H15Al
InChIKey:VOITXYVAKOUIBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.1195
Molecular Formula:C7H5NO3
InChIKey:BXRFQSNOROATLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:CCXCDGPNZOAAKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:YMHOPFPBSLGXDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.451
Molecular Formula:C5H5Cl3O2
InChIKey:JYNDMWZEMQAWTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:FTZILAQGHINQQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.1791
Molecular Formula:C8H12O3
InChIKey:IXJXPZXXBAKDSU-RNFRBKRXSA-N
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Compound Information
Molecular Weight:297.3484
Molecular Formula:C18H19NO3
InChIKey:DTTXEQHDFHHDME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:Not Available
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:IYAOYVAFBKAUBZ-UTCJRWHESA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:ANISOHQJBAQUQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:QDTMXXIXRPMTJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:OMIGHNLMNHATMP-UHFFFAOYSA-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:100.1158
Molecular Formula:C5H8O2
InChIKey:JIGUQPWFLRLWPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.1566
Molecular Formula:C10H7F3O2
InChIKey:PLJJYOFLDJQAHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:CFVWNXQPGQOHRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.1821
Molecular Formula:C10H8N2O3
InChIKey:KSSHQPCVMZULSQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.0872
Molecular Formula:C5H5F3O2
InChIKey:VBHXIMACZBQHPX-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:133.117
Molecular Formula:C7H12LiNO
InChIKey:SDALWGHOVDXNDQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:RYHBNJHYFVUHQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:OJNXPAPLAAGFBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:QJDSREBWOROHEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.4284
Molecular Formula:C18H33P
InChIKey:WLPUWLXVBWGYMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:QKOWNVUYUQGDCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:325.2369
Molecular Formula:C14H11CrNO5
InChIKey:ZXAUCTKZQWGUBH-RQLHABPXSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:IGFYQTMEAMWUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:RAVPYDHJNSDTQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:CTJCQZRLMPBOEU-QWHCGFSZSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:RYEMNFJHCBZHAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:MJJURONWODRKDU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-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:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-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:144.1684
Molecular Formula:C7H12O3
InChIKey:NDWUBGAGUCISDV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:DBPFRRFGLYGEJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.3165
Molecular Formula:C12H27P
InChIKey:TUQOTMZNTHZOKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1467
Molecular Formula:C8H11P
InChIKey:HASCQPSFPAKVEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.2264
Molecular Formula:C11H13NO2
InChIKey:MCUSVUGKVLTTBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:331.577
Molecular Formula:C11H13Cl3O5
InChIKey:XZTMWJJEBMUFBN-MLWJPKLSSA-N
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Compound Information
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:IQGFRCLYBUQZED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2091
Molecular Formula:C12H11F3O3
InChIKey:NHSRCNKRFCNDGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:ZMCZESBVMOWZIA-SNVBAGLBSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:PDCIMZYXJDXUIL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:OTINXZDMBYPTCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:143.1852
Molecular Formula:C10H9N
InChIKey:RJTHVQJBBSFMAH-PLNGDYQASA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:VLCAYQIMSMPEBW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.3163
Molecular Formula:C15H20O5
InChIKey:XBGJVJUOHGIWKF-TZMCWYRMSA-N
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Compound Information
Molecular Weight:236.2637
Molecular Formula:C13H16O4
InChIKey:SRNMCKBEETZALF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:NWVVVBRKAWDGAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.128
Molecular Formula:C12H12Cl2O3
InChIKey:PKVPQMXENZTNPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:OYMWCVFOKIBYIS-VURMDHGXSA-N
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Compound Information
Molecular Weight:112.1729
Molecular Formula:C6H12N2
InChIKey:IMNIMPAHZVJRPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1491
Molecular Formula:C9H7FO2
InChIKey:DLCLLGYYNXJCMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:ZMCZESBVMOWZIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:IYAOYVAFBKAUBZ-ZZXKWVIFSA-N
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Compound Information
Molecular Weight:173.2111
Molecular Formula:C11H11NO
InChIKey:KWHCFQDPVYYUNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:VLCAYQIMSMPEBW-RXMQYKEDSA-N
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Compound Information
Molecular Weight:204.2203
Molecular Formula:C9H16O5
InChIKey:PXVMFUIMDOJSQF-SFYZADRCSA-N
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Compound Information
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:IVLICPVPXWEGCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.3163
Molecular Formula:C15H20O5
InChIKey:XBGJVJUOHGIWKF-OCCSQVGLSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:CTJCQZRLMPBOEU-CHWSQXEVSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:REFRKUNIVJSIMQ-APPZFPTMSA-N
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Compound Information
Molecular Weight:216.231
Molecular Formula:C10H16O5
InChIKey:MDBWODYZTISSKP-SFYZADRCSA-N
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Compound Information
Molecular Weight:259.2988
Molecular Formula:C12H21NO5
InChIKey:JUBPNAGDMOAOGG-RKDXNWHRSA-N
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Compound Information
Molecular Weight:289.2833
Molecular Formula:C15H15NO5
InChIKey:GSMGDWVEWHQGEG-BXKDBHETSA-N
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Compound Information
Molecular Weight:315.3621
Molecular Formula:C15H25NO6
InChIKey:MDGJAPMWSVGXHY-MNOVXSKESA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:RYEMNFJHCBZHAR-SECBINFHSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:HFGYAXCVTHXUQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:ICMBTQSRUNSRKI-UHFFFAOYSA-N
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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:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:455.402
Molecular Formula:C19H17CrNO7S
InChIKey:XQCDIUKHSRLCFK-AMAREMMUSA-N
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Compound Information
Molecular Weight:162.1837
Molecular Formula:C7H14O4
InChIKey:RDQZKGXBASSFED-LWOQYNTDSA-N
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Compound Information
Molecular Weight:56.0633
Molecular Formula:C3H4O
InChIKey:TVDSBUOJIPERQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:118.1742
Molecular Formula:C6H14O2
InChIKey:DHKHKXVYLBGOIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.2625
Molecular Formula:C13H15NO4
InChIKey:RMEOBFUQPIRRCR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.3981
Molecular Formula:C15H30O
InChIKey:XGQJZNCFDLXSIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.177
Molecular Formula:C6H6S
InChIKey:RMVRSNDYEFQCLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.504
Molecular Formula:C7H9Cl3O3
InChIKey:RBPDBOIBTGQVMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:AYSSQBKSBWLOAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:FPYUJUBAXZAQNL-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:212.265
Molecular Formula:C10H12O3S
InChIKey:SSABBQQTYHZSBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:PQEFHYQZCYQJTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:Not Available
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Compound Information
Molecular Weight:239.2246
Molecular Formula:C11H13NO5
InChIKey:JZPIWEQHPIEJHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:ZWLUXSQADUDCSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2485
Molecular Formula:C13H14O3
InChIKey:ZPRGUSJYYIEKBY-CMDGGOBGSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:GPJOKVDICCIMEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.381
Molecular Formula:C15H20O5S
InChIKey:PXLDIIJRCNPKGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.1885
Molecular Formula:C9H11NO3
InChIKey:JHVANAPGWSZENE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:KUCOHFSKRZZVRO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:VCYUPWAOEBCJLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2045
Molecular Formula:C9H14O5
InChIKey:NSUFXJREWSCJGN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.84
Molecular Formula:C3Cl4F2O
InChIKey:MXYOKVCIXGJEFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:370.5234
Molecular Formula:C21H38O5
InChIKey:JCSAIUWGEBTGMX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2179
Molecular Formula:C13H10O
InChIKey:RWCCWEUUXYIKHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.2213
Molecular Formula:C12H12O4
InChIKey:LLRQAVMSQWZVOG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-DAXSKMNVSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:FXLOVSHXALFLKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.335
Molecular Formula:C15H14O2S
InChIKey:RELSQPIJAMGUEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.347
Molecular Formula:C12H26N2O2
InChIKey:KVPOKOJWBKBPNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:QKLCQKPAECHXCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.187
Molecular Formula:C9H18LiN
InChIKey:ANYSGBYRTLOUPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:GNFRWNFFSVUEEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:DTUQWGWMVIHBKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.722
Molecular Formula:C6H15ClSi
InChIKey:BCNZYOJHNLTNEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.267
Molecular Formula:C10H12OS
InChIKey:YKVYOBIJIBNJSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2378
Molecular Formula:C12H14O3
InChIKey:UCBSJMZGFLPCCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.358
Molecular Formula:C9H14SSi
InChIKey:VJMQFIRIMMSSRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:131.1729
Molecular Formula:C6H13NO2
InChIKey:VSFJOMFYABROHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.1931
Molecular Formula:C8H13NO4
InChIKey:UOQKTPJWYASECT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:DWZKIUVIKLWHDJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:YGHRJJRRZDOVPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:133.1027
Molecular Formula:C4H7NO4
InChIKey:PVOVDKWDSQCJAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:439.3968
Molecular Formula:C22H19F6N3
InChIKey:GHDDFGGGNBCPGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.0526
Molecular Formula:C4NO4
InChIKey:PMECZTORDHBLDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.06
Molecular Formula:C4H3F3O3
InChIKey:XGLLQDIWQRQROJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.3108
Molecular Formula:C13H22O5
InChIKey:IZPSKHDHLZETNJ-CMDGGOBGSA-N
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Compound Information
Molecular Weight:288.2149
Molecular Formula:C9H22O6P2
InChIKey:STJWVOQLJPNAQL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.7338
Molecular Formula:C4NiO4
InChIKey:AWDHUGLHGCVIEG-UHFFFAOYSA-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:151.1195
Molecular Formula:C7H5NO3
InChIKey:ZETIVVHRRQLWFW-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:284.4342
Molecular Formula:C17H32O3
InChIKey:RSBOFIGSCSSBQJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.1567
Molecular Formula:C10H14O5V
InChIKey:JFHJZWAQYMGNBE-XHTSQIMGSA-L
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Compound Information
Molecular Weight:60.0843
Molecular Formula:O2Si
InChIKey:VYPSYNLAJGMNEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.345
Molecular Formula:C13H18O3S
InChIKey:QUZBUULEUTXSTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2673
Molecular Formula:C11H20O3
InChIKey:PRLHSEHOSFGKNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.393
Molecular Formula:C16H20O4S
InChIKey:FEMBSEFNGPOWLF-JLHYYAGUSA-N
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Compound Information
Molecular Weight:208.1919
Molecular Formula:C8H17O4P
InChIKey:KMJCWEYBVMRBAX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.1626
Molecular Formula:C8H10O4
InChIKey:UECSRZXCAQKDHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.213
Molecular Formula:C8H8O2S
InChIKey:UJTPZISIAWDGFF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2393
Molecular Formula:C15H10O
InChIKey:YMNKUHIVVMFOFO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.4621
Molecular Formula:C16H36FN
InChIKey:FPGGTKZVZWFYPV-UHFFFAOYSA-M
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:GTFGWLIGRMYDJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:OESYTWLVWKQIHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2264
Molecular Formula:C11H17P
InChIKey:IBCOCCUYWHQQQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.3285
Molecular Formula:C19H16O3
InChIKey:HGHHPPNNCKTKON-RVDMUPIBSA-N
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Compound Information
Molecular Weight:128.1916
Molecular Formula:C7H13NO
InChIKey:SIMWBLBMZJOMID-UHFFFAOYSA-O
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Compound Information
Molecular Weight:210.155
Molecular Formula:C8H20BrN
InChIKey:HWCKGOZZJDHMNC-UHFFFAOYSA-M
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:KUIZKZHDMPERHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.0954
Molecular Formula:C4H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:311.3765
Molecular Formula:C22H17NO
InChIKey:UDMVPZWJLNEKTJ-LTGZKZEYSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.392
Molecular Formula:C16H20O5S
InChIKey:SVXATBFETFOZKY-UHFFFAOYSA-N
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