Standard Article

The Reimer–Tiemann Reaction

  1. Hans Wynberg,
  2. Egbert W. Meijer

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or028.01

Organic Reactions

Organic Reactions

How to Cite

Wynberg, H. and Meijer, E. W. 2005. The Reimer–Tiemann Reaction. Organic Reactions. 28:1:1–36.

Author Information

  1. The University, Groningen, The Netherlands

Publication History

  1. Published Online: 15 JUL 2005

Chemistry Terms

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Abstract

The Reimer–Tiemann reaction owes its name to two young German chemists, Karl Reimer and Ferdinand Tiemann. In 1876 they isolated and identified hydroxyaldehydes as the principal reaction products of phenol and chloroform in alkaline medium. The scope of this reaction was enlarged in 1884 by von Auwers, who discovered the chlorine-containing cyclohexadienones as by-products in the formylation of alkylphenols. The ring-expansion products, namely, chloropyridines, were first noted by Ciamician when he subjected pyrroles to Reimer–Tiemann reaction conditions. Nearly half a century passed before Woodward recognized that the conversion of an alkylphenol to a substituted cyclohexadienone could lead to the synthesis of terpenes and steroids containing an angular methyl group. Although the method failed as a preparatively useful approach to the synthesis of steroids, an A/B trans-fused hexahydrophenanthrene was prepared using a Reimer–Tiemann reaction. The reaction was last reviewed some 20 years ago.

It is convenient to divide the Reimer–Tiemann reaction into a normal and abnormal transformation depending on the reaction products. A normal Reimer–Tiemann reaction is one in which a phenol (or electron-rich aromatic such as pyrrole) yields one or more aldehydes on treatment with chloroform and alkali. The abnormal Reimer–Tiemann reaction product can be subdivided further into cyclohexadienones and ring-expansion products:

  1. When ortho- or para-substituted phenols are subjected to the Reimer–Tiemann reaction conditions, 2,2- or 4,4-disubstituted cyclohexadienones may be obtained in addition to the normal products. Several alkylphenols, alkylnaphthols, and tetralols have been converted into cyclohexadienones, whereas some alkylpyrroles are converted to pyrrolines in this manner.

  2. A variety of five-membered rings yield ring-expansion products when subjected to the Reimer–Tiemann reaction conditions. These products are formed in addition to the normal products.

In addition to aromatic aldehydes, cyclohexadienones, pyrrolines, and ring-expansion products, a variety of other products have been noted, isolated, and identified in a few cases. All these by-products are discussed.

Keywords:

  • Reimer-Tiemann reaction;
  • dihalocarbene reaction;
  • phenoxide anions;
  • scope;
  • limitations;
  • phenols;
  • alkylphenols;
  • naphthols;
  • halophenols;
  • pyrimidines;
  • substituted phenols;
  • pyrroles;
  • hydroxyphenols;
  • alkoxyphenols;
  • heterocyclic phenols;
  • experimental procedures

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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:303.267
Molecular Formula:C16H24Cl2O
InChIKey:LJEFTNVYDZZYTA-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:110.1106
Molecular Formula:C6H6O2
InChIKey:YCIMNLLNPGFGHC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:DSXKMMAQDSAZAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1506
Molecular Formula:C7H8N2O2
InChIKey:KIHAIKJZUMYBSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:Not Available
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Compound Information
Molecular Weight:269.2521
Molecular Formula:C15H11NO4
InChIKey:JSRALSBEQIBCSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1017
Molecular Formula:C6H5FO
InChIKey:HFHFGHLXUCOHLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:BAKYASSDAXQKKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1017
Molecular Formula:C6H5FO
InChIKey:SJTBRFHBXDZMPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.2744
Molecular Formula:C14H15NO2
InChIKey:GQMMTOXATFUFOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.1302
Molecular Formula:C8H6O5
InChIKey:WVDGHGISNBRCAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2338
Molecular Formula:C13H12O
InChIKey:HJSPWKGEPDZNLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:KNQVIRRXVOTGGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.189
Molecular Formula:C6H6N2O2S
InChIKey:FXFOKYOZJILGHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:XLIMLVMYIYSMIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1405
Molecular Formula:C6H8N2O
InChIKey:UQFHLJKWYIJISA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:IXWOUPGDGMCKGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:JKOQLKOTRQTLOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:241.242
Molecular Formula:C14H11NO3
InChIKey:YAXJIGOPALNVBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.1675
Molecular Formula:C10H7NO3
InChIKey:APVGWZCNIAHMDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:VXSCPERJHPWROZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:205.081
Molecular Formula:C9H10Cl2O
InChIKey:OVJHGAXYMVWABG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1133
Molecular Formula:C5H6N2O2
InChIKey:SHVCSCWHWMSGTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:XPYRAGGZLQXCBO-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:140.567
Molecular Formula:C7H5ClO
InChIKey:PTXQLRMMKQTSDX-AATRIKPKSA-N
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Compound Information
Molecular Weight:153.1817
Molecular Formula:C7H11N3O
InChIKey:KREIGOYUONNOJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:DOHOPUBZLWVZMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.0969
Molecular Formula:C5H4N2O3
InChIKey:OHAMXGZMZZWRCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.108
Molecular Formula:C10H12Cl2O
InChIKey:SROIDXDTTVPRNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:FSNWAMYECSEIEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:WZUODJNEIXSNEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:KUFFULVDNCHOFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.1895
Molecular Formula:C12H8O4
InChIKey:LPRBZICETYEWOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.625
Molecular Formula:C11H7ClO2
InChIKey:WDZQQLVXLJIHFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:FZHSPPYCNDYIKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:XBYOCRCRHQJSIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:LIADJWREMDHKHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:Not Available
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:PFNMQJSEHLYYLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:CLFRCXCBWIQVRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.0862
Molecular Formula:C4H4N2O3
InChIKey:HNYOPLTXPVRDBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1118
Molecular Formula:C7H5FO2
InChIKey:NWDHTEIVMDYWQJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:JODRRPJMQDFCBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.017
Molecular Formula:C7H5BrO2
InChIKey:OCBOCCOUCDGNKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1739
Molecular Formula:C9H10O3
InChIKey:YXAGWJLMBDENHX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:PETRWTHZSKVLRE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:KAESVJOAVNADME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.1568
Molecular Formula:C9H8O5
InChIKey:QXYHEHLDBWYGKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:QNZWAJZEJAOVPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:KMNWXQCQWZYMEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:CTRCOIVJCBPCPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1133
Molecular Formula:C5H6N2O2
InChIKey:BPSGVKFIQZZFNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.098
Molecular Formula:C10H11BrO
InChIKey:XNPHONZZCGCBTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.118
Molecular Formula:C11H12Cl2O
InChIKey:SFPYMARLVCBPNZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.556
Molecular Formula:C6H5ClO
InChIKey:ISPYQTSUDJAMAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:TUAMRELNJMMDMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1106
Molecular Formula:C6H6O2
InChIKey:Not Available
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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:181.1918
Molecular Formula:C8H11N3O2
InChIKey:OAYMAMBOGIWBFB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:QHPQWRBYOIRBIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.017
Molecular Formula:C7H5BrO2
InChIKey:UOTMHAOCAJROQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:KJCVRFUGPWSIIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1308
Molecular Formula:C8H6O4
InChIKey:NXZBZWZORYEIJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.2557
Molecular Formula:C11H15N3O2
InChIKey:DUSWZCFKWDXOKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ZRUOTKQBVMWMDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.055
Molecular Formula:C8H8Cl2O
InChIKey:MJRRCEHODULPAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.545
Molecular Formula:C5H4ClN
InChIKey:Not Available
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:LHGVFZTZFXWLCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.556
Molecular Formula:C6H5ClO
InChIKey:WXNZTHHGJRFXKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:FQNZXGZKHKUKRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:SCWNNOCLLOHZIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:TUVJXIJXRIXXMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.169
Molecular Formula:C4H6N2S
InChIKey:SBQPDLGIWJRKBS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1308
Molecular Formula:C8H6O4
InChIKey:UTCFOFWMEPQCSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1017
Molecular Formula:C6H5FO
InChIKey:RHMPLDJJXGPMEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:YXVFYQXJAXKLAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:CJRTYYDFXSSBBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:PXIKRTCSSLJURC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:ZVCQQLGWGRTXGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.179
Molecular Formula:C5H6N2OS
InChIKey:XYSWAIBGBOZMSN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3505
Molecular Formula:C15H24O
InChIKey:Not Available
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Compound Information
Molecular Weight:93.1038
Molecular Formula:C6H5O
InChIKey:FABJBXYZKYBFAM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1112
Molecular Formula:C6H6O
InChIKey:ISWSIDIOOBJBQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:VGSOCYWCRMXQAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.017
Molecular Formula:C7H5BrO2
InChIKey:HXTWKHXDFATMSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1405
Molecular Formula:C6H8N2O
InChIKey:WHEQVHAIRSPYDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.017
Molecular Formula:C7H5BrO2
InChIKey:MKKSTJKBKNCMRV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:255.108
Molecular Formula:C11H11BrO2
InChIKey:FBBQMMFVJJINNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1794
Molecular Formula:C11H8O3
InChIKey:ALKYHXVLJMQRLQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:OVYWMEWYEJLIER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.1846
Molecular Formula:C10H9NO
InChIKey:LUOZEWPJSYBORW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.1467
Molecular Formula:C8H8O4
InChIKey:LBKFGYZQBSGRHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.021
Molecular Formula:C7H6Cl2O
InChIKey:CJMZXIRJUSCLOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:YCOXTKKNXUZSKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.028
Molecular Formula:C7H6Cl2O
InChIKey:JFCMAIACBGBZRX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.3285
Molecular Formula:C19H16O3
InChIKey:BSNNCWZXRJKCBZ-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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:99.924
Molecular Formula:CH2Cl2O
InChIKey:QZRGJVDKQVDBDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:UMKXSOXZAXIOPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1506
Molecular Formula:C7H8N2O2
InChIKey:SYQKIBHUNFXIDV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.2184
Molecular Formula:C9H13N3O2
InChIKey:YMIMSTFOLJPCFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:YSHWKKGQACCKOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.1574
Molecular Formula:C9H8O4
InChIKey:FKOWPXKNFXHWCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.18
Molecular Formula:C11H8O2
InChIKey:OITQDWKMIPXGFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:XCRPPAPDRUBKRJ-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:166.1308
Molecular Formula:C8H6O4
InChIKey:YBIDDVOKTAHFOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1234
Molecular Formula:C6H6N2O3
InChIKey:VOXFLZILKSTBGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.3228
Molecular Formula:C20H14O4
InChIKey:KJFMBFZCATUALV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:Not Available
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:WTHUWXPBPNTSHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:HDHQZCHIXUUSMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.615
Molecular Formula:C10H7ClO
InChIKey:FPBMWSBRLLFCEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.1947
Molecular Formula:C11H9NO2
InChIKey:ZWZHEKQLINGDOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:KBHBGCGYQBSXRO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:Not Available
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:MVTWVXYIKIVAOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.1733
Molecular Formula:C9H10O4
InChIKey:KCDXJAYRVLXPFO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.021
Molecular Formula:C7H6Cl2O
InChIKey:CJMZXIRJUSCLOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:IWDCLRJOBJJRNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1234
Molecular Formula:C6H6N2O3
InChIKey:LRVSBYJDLSIFGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:PKDVWOVKDPEBQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:WBIZZNFQJPOKDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:CHNYVNOFAWYUEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:YGSDEFSMJLZEOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:JWAZRIHNYRIHIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.017
Molecular Formula:C7H5BrO2
InChIKey:LQTXMBDCLHZDAM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.1947
Molecular Formula:C11H9NO2
InChIKey:BESILXADEIWIQV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:JDWWIEFMFPWBST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.2456
Molecular Formula:C10H15N3O
InChIKey:MONLCVZETJZNSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.1302
Molecular Formula:C8H6O5
InChIKey:BCEQKAQCUWUNML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:MGSRCZKZVOBKFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:CHWNEIVBYREQRF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:QVNGLKIFRNFPQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:ZRNGCROWVVZCLT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.556
Molecular Formula:C6H5ClO
InChIKey:HORNXRXVQWOLPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.0868
Molecular Formula:C4H4N2O2
InChIKey:ISAKRJDGNUQOIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:FRMMUYMRVFIPSC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.1568
Molecular Formula:C9H8O5
InChIKey:OIHYUJVAHOIZNC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:OMXBWJYYNNGFIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:315.278
Molecular Formula:C17H24Cl2O
InChIKey:XJTSBNYPOAHHRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.18
Molecular Formula:C11H8O2
InChIKey:PLCQXZXTFCITAJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:ZMOMCILMBYEGLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.021
Molecular Formula:C7H6Cl2O
InChIKey:QTQDJVCIRFEATI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:YSNKZJBCZRIRQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:KLIDCXVFHGNTTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:FUGKCSRLAQKUHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.1928
Molecular Formula:C11H8N2O3
InChIKey:RBRXTBFLLNKIFY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.1403
Molecular Formula:C9H6O6
InChIKey:JDCDHJDPNCNNKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.017
Molecular Formula:C7H5BrO2
InChIKey:STBGLXMINLWCNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:JJVNINGBHGBWJH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1118
Molecular Formula:C7H5FO2
InChIKey:GBJJCODOZGPTBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:DGXAGETVRDOQFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1207
Molecular Formula:C7H6O3
InChIKey:IJFXRHURBJZNAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:XBGRTOBXVRCNTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:RECUKUPTGUEGMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.007
Molecular Formula:C6H5BrO
InChIKey:GZFGOTFRPZRKDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.3329
Molecular Formula:C21H14O5
InChIKey:DLKSZUYLFMDPBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:Not Available
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:XZXRAQXNXSBHGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:ADWNVCAUNIBNLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1106
Molecular Formula:C6H6O2
InChIKey:QIGBRXMKCJKVMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:SMQUZDBALVYZAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1739
Molecular Formula:C9H10O3
InChIKey:NDGVJTXAOLGFKK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:IPPQNXSAJZOTJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:XXTRGLCPRZQPHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1308
Molecular Formula:C8H6O4
InChIKey:YOEUNKPREOJHBW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:143.164
Molecular Formula:C5H5NO2S
InChIKey:IEEKUCZFESYYPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:HWJJTWWMMHEEAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1308
Molecular Formula:C8H6O4
InChIKey:AYZFTYFURGCPEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.18
Molecular Formula:C11H8O2
InChIKey:NTCCNERMXRIPTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.154
Molecular Formula:C4H5NOS
InChIKey:ZMEVDFFLOPFGCR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:MIVVOBJNDVJIFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.206
Molecular Formula:C6H8N2OS
InChIKey:OCOHPSHRDKBGOZ-UHFFFAOYSA-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:140.1118
Molecular Formula:C7H5FO2
InChIKey:ONRPXRPUBXXCCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.0963
Molecular Formula:C5H4N2O4
InChIKey:IOZLDDRCFVAFDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.007
Molecular Formula:C6H5BrO
InChIKey:Not Available
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Compound Information
Molecular Weight:248.0179
Molecular Formula:C7H5IO2
InChIKey:UPUMRAVJDXWXMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.216
Molecular Formula:C7H8N2O2S
InChIKey:BFRBZGHADWDLCV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.18
Molecular Formula:C11H8O2
InChIKey:BFAUDJHQXKMZFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.1387
Molecular Formula:C6H7N3O2
InChIKey:PNPAUTSOHWSEGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:YYWTTXQJHPXJIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:ZSKGQVFRTSEPJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1094
Molecular Formula:C6H5NO2
InChIKey:ICDSWZBXIZCMHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.0078
Molecular Formula:C6H5IO
InChIKey:FXTKWBZFNQHAAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ILEIUTCVWLYZOM-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:142.179
Molecular Formula:C5H6N2OS
InChIKey:HWGBHCRJGXAGEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.917
Molecular Formula:CCl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:28.0101
Molecular Formula:CO
InChIKey:UGFAIRIUMAVXCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:MWOOGOJBHIARFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.2285
Molecular Formula:C10H13N3O3
InChIKey:IHUAUWFPKUZLNT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1827
Molecular Formula:C10H8N2O2
InChIKey:WTDXDRUHQKVYKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:GDEHXPCZWFXRKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.011
Molecular Formula:C7H4Cl2O2
InChIKey:WWFRBIPLCLSKNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2173
Molecular Formula:C13H10O2
InChIKey:NAUBSKHQFFCEMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.001
Molecular Formula:C6H4Cl2O
InChIKey:VPOMSPZBQMDLTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:PWFKERWVXUISSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:NKTOLZVEWDHZMU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:QOPODVCTNOEUPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.1846
Molecular Formula:C10H9NO
InChIKey:Not Available
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:LLVQQQQUKUEOOW-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:125.1286
Molecular Formula:C5H7N3O
InChIKey:Not Available
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Compound Information
Molecular Weight:140.1118
Molecular Formula:C7H5FO2
InChIKey:FDUBQNUDZOGOFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.007
Molecular Formula:C6H5BrO
InChIKey:MNOJRWOWILAHAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.1403
Molecular Formula:C9H6O6
InChIKey:GUHCCUCTOINTAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1118
Molecular Formula:C7H5FO2
InChIKey:QSBHJTCAPWOIIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.108
Molecular Formula:C10H12Cl2O
InChIKey:YJKMETCJDBNRPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:LUIMJXRWZCXGCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:USROEJBTXWQSKM-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:205.081
Molecular Formula:C9H10Cl2O
InChIKey:PKAIGMXSFCHJKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:BPRYUXCVCCNUFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:RLSSMJSEOOYNOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:NMPPTQWNUWOQDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:HGNLFMRNEFPDHZ-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:98.916
Molecular Formula:CCl2O
InChIKey:Not Available
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Compound Information
Molecular Weight:94.1112
Molecular Formula:C6H6O
InChIKey:ISWSIDIOOBJBQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.028
Molecular Formula:C7H6Cl2O
InChIKey:JFCMAIACBGBZRX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.021
Molecular Formula:C7H5Cl2O
InChIKey:BCIUVXAZEFKBES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.021
Molecular Formula:C7H6Cl2O
InChIKey:CJMZXIRJUSCLOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.021
Molecular Formula:C7H6Cl2O
InChIKey:CJMZXIRJUSCLOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:SMQUZDBALVYZAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:KAESVJOAVNADME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:PMOWTIHVNWZYFI-AATRIKPKSA-N
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Compound Information
Molecular Weight:224.2115
Molecular Formula:C14H8O3
InChIKey:GCDBEYOJCZLKMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:245.145
Molecular Formula:C12H14Cl2O
InChIKey:NGUAQXBQYDKBAX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.184
Molecular Formula:C10H9NO2
InChIKey:TUWARWGEOHQXCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.1568
Molecular Formula:C9H7NO3
InChIKey:AVBUASQLAQAKAM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.604
Molecular Formula:C9H6ClN
InChIKey:FLORQCMDMHHIHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.081
Molecular Formula:C9H10Cl2O
InChIKey:UVJDEXDQIXWVCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.055
Molecular Formula:C9H6BrN
InChIKey:ZGIKWINFUGEQEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.155
Molecular Formula:C13H13Cl2N
InChIKey:XDHXFLMZALFNSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.63
Molecular Formula:C10H8ClNO
InChIKey:LKUYYPIALQJFEW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.1189
Molecular Formula:C7H5NO4
InChIKey:Not Available
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Compound Information
Molecular Weight:147.1739
Molecular Formula:C9H9NO
InChIKey:FSOPPXYMWZOKRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.124
Molecular Formula:C13H10Cl2O
InChIKey:OPJMXAXCOLJJHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.014
Molecular Formula:C11H11BrCl2O
InChIKey:KUEJGHLTNFMPHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SIKJAQJRHWYJAI-UHFFFAOYSA-N
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