Standard Article

The Friedländer Synthesis of Quinolines

  1. Chia-Chung Cheng,
  2. Shou-Jen Yan

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or028.02

Organic Reactions

Organic Reactions

How to Cite

Cheng, C.-C. and Yan, S.-J. 2005. The Friedländer Synthesis of Quinolines. Organic Reactions. 28:2:37–201.

Author Information

  1. Mid-America Cancer Center Program, University of Kansas Medical Center, Kansas City, Kansas

Publication History

  1. Published Online: 15 JUL 2005

Chemistry Terms

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Abstract

Friedländer prepared quinoline in 1882 by the condensation of o-aminobenzaldehyde with acetaldehyde in the presence of sodium hydroxide. This type of reaction has since been extensively explored and, in its most general form, can be defined as an acid- or base-catalyzed condensation followed by a cyclodehydration between an o-amino-substituted aromatic aldehyde, ketone, or derivative thereof with an appropriately substituted aldehyde, ketone, or other carbonyl compound containing a reactive α-methylene group. Some quinolines can also be prepared simply by heating a mixture of the reactants with or without a solvent.

Because both reactants contain a carbonyl group, certain quinolines can be prepared from a single starting compound. Of historic interest is the formation of the dye flavaniline from acetanilide. When acetanilide is heated with zinc chloride, the acetyl group of some molecules migrates to the ortho position, and that of others migrates to the para position. The resulting mixture of o-acetylaniline and p-acetylaniline then undergoes Friedländer condensation to form flavaniline.

Two related quinoline syntheses, the Pfitzinger reaction and the Niementowski reaction, can be considered as extensions of the Friedländer synthesis. The Pfitzinger reaction uses an isatic acid or isatin and the Niementowski reaction uses an anthranilic acid for condensation to form a 4-quinolinecarboxylic acid and a 4-hydroxyquinoline, respectively.

Several other related reactions, such as the Combes quinoline synthesis, the Doebner–Miller quinoline synthesis, and the Skraup quinoline synthesis, use different types of starting compounds. It is of interest that all of the six aforementioned syntheses of quinolines were discovered within a period of 14 years in the latter part of the nineteenth century, undoubtedly reflecting many scientific interests and commercial activities at that time, including the isolation of quinolines from coal tar, the manufacture of dyes, and studies of natural products such as alkaloids.

Keywords:

  • Friedlander synthesis;
  • quinolines;
  • scope;
  • limitations;
  • aminocarbonyl component;
  • active methylene component;
  • experimental procedures;
  • aminobenzaldehdyes;
  • condensations;
  • aminoacetophenone hydrochloride;
  • dimethylacetals;
  • aminobenzophenone;
  • aminoacroleins;
  • amino heterocyclic carbonyls

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.135
Molecular Formula:C3H6O4S
InChIKey:ZYKVCFGIFGTEPR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:35.0458
Molecular Formula:H5NO
InChIKey:VHUUQVKOLVNVRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:JDXYSCUOABNLIR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2527
Molecular Formula:C15H10N2O
InChIKey:YJSPDKPPDSKBQZ-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:212.2902
Molecular Formula:C14H16N2
InChIKey:WITFUKGYXJRVRQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:XYIBRDXRRQCHLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2472
Molecular Formula:C13H12N2O
InChIKey:RBVDBXWGUKZVBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.333
Molecular Formula:C15H12N2O2S
InChIKey:NDRCNBOULJLYJP-UHFFFAOYSA-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:160.1247
Molecular Formula:C6H8O5
InChIKey:ZOKLUHBZBGHBAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.1561
Molecular Formula:C9H6N2O2
InChIKey:ZXVRNZRQQRBDLX-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2958
Molecular Formula:C16H14N2
InChIKey:YLLXQMXKVVPUMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.2383
Molecular Formula:C12H13N
InChIKey:VFCWSYWYYWLKGY-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:154.594
Molecular Formula:C8H7ClO
InChIKey:BUZYGTVTZYSBCU-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:213.1922
Molecular Formula:C11H7N3O2
InChIKey:KWHWFTSHDPJOTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.1671
Molecular Formula:C7H11NO3
InChIKey:DQYGBMLEVQLDQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.1776
Molecular Formula:C11H7NO4
InChIKey:YHUVMHKAHWKQBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1827
Molecular Formula:C10H8N2O2
InChIKey:CZWHVUCAESEVTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:IQQDNMHUOLMLNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.045
Molecular Formula:C8H7BrO
InChIKey:LIGACIXOYTUXAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.3129
Molecular Formula:C16H17N
InChIKey:XTDCLHQPQCFOJB-TXEJJXNPSA-N
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Compound Information
Molecular Weight:157.2117
Molecular Formula:C11H11N
InChIKey:FBOFHVFMPNNIKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:FXWFZIRWWNPPOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.2692
Molecular Formula:C15H12N2
InChIKey:CIHDZAQRRFHMLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.524
Molecular Formula:C3H5ClO
InChIKey:BULLHNJGPPOUOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.3077
Molecular Formula:C17H15N
InChIKey:CEGOBACMMLDFSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1519
Molecular Formula:C7H10O4
InChIKey:OYQVQWIASIXXRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:ZPKRDBXIPFYPTF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:MGZQQKMLEDHPMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:289.2402
Molecular Formula:C14H11NO6
InChIKey:YQUXTBIUEYCWPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.238
Molecular Formula:C9H9NO2S
InChIKey:BBNNLJMGPASZPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:AJKVQEKCUACUMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.1412
Molecular Formula:C6H9NO2
InChIKey:QKDFXHZLODLGER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:LOAUVZALPPNFOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:Not Available
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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:109.1259
Molecular Formula:C6H7NO
InChIKey:IGJQUJNPMOYEJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:HUUPVABNAQUEJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.1788
Molecular Formula:C11H7NO2
InChIKey:FZYGATLKLHAMAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.1959
Molecular Formula:C11H9N
InChIKey:ZOWDOAFSVSVRJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.264
Molecular Formula:C16H11NO2
InChIKey:JIPUGCBCIYYRSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.29
Molecular Formula:C17H13NO3
InChIKey:IDOPUTCYAPROSF-QGOAFFKASA-N
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Compound Information
Molecular Weight:185.2218
Molecular Formula:C12H11NO
InChIKey:OKDWGFQXJYJNIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:UJBOOUHRTQVGRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.219
Molecular Formula:C4H5NOS2
InChIKey:JKLZCQWVERBDEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:OILAIQUEIWYQPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3157
Molecular Formula:C15H20O6
InChIKey:BNHRUAKQHCIHOS-HUUCEWRRSA-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:250.2521
Molecular Formula:C15H10N2O2
InChIKey:DGUYOGQXNQODRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:FSEXLNMNADBYJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1038
Molecular Formula:C4H6N2
InChIKey:CSIFGMFVGDBOQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.498
Molecular Formula:C2H3ClO
InChIKey:QSKPIOLLBIHNAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.108
Molecular Formula:C8H6BrNO2S
InChIKey:KSKSEVVFIOHIAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.0614
Molecular Formula:C3H3NO2
InChIKey:MLIREBYILWEBDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:MJUHIAWSJRKXSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:FWNRRWJFOZIGQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:WNHRJTQJYZFVCZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:NLGDIRPNWGZGLI-MDZDMXLPSA-N
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Compound Information
Molecular Weight:247.2912
Molecular Formula:C17H13NO
InChIKey:DLKVUJVTIFJMTE-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:232.325
Molecular Formula:C11H8N2S2
InChIKey:SMVBAROABQBGCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:BDVKAMAALQXGLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.1461
Molecular Formula:C8H7NO3
InChIKey:KAPAJCPOBXIQRP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:GTDQGKWDWVUKTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:LCNMLKMSZJKXEY-AEIGPULVSA-N
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Compound Information
Molecular Weight:170.1674
Molecular Formula:C10H6N2O
InChIKey:WNRMLIGSXULUPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.657
Molecular Formula:C8H6ClNO2S
InChIKey:HAQGVGPNKGGSMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZEXFAVZTIZXHFA-ONEGZZNKSA-N
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Compound Information
Molecular Weight:206.2426
Molecular Formula:C14H10N2
InChIKey:KTDMTKZWKXFJHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.228
Molecular Formula:C8H9NOS
InChIKey:QFTUPSZZEJQOJX-UHFFFAOYSA-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:201.2212
Molecular Formula:C12H11NO2
InChIKey:QPMSEXVWDWSUNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2392
Molecular Formula:C11H12N4O
InChIKey:NWRMZPPJWLOAFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:KCKZIWSINLBROE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2915
Molecular Formula:C14H17N
InChIKey:XQGPXSFBKUTAGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:363.229
Molecular Formula:C15H11BrN2O2S
InChIKey:SJYLDDPWIKAOJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.3356
Molecular Formula:C16H19NO
InChIKey:JEKSYKVSGLVGKR-MVOHADHWSA-O
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Compound Information
Molecular Weight:242.2732
Molecular Formula:C14H14N2O2
InChIKey:DPNXOZFTZHIWAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:269.2554
Molecular Formula:C14H11N3O3
InChIKey:TWFSBXPDFLNZCX-BENRWUELSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:KIECIMHLAZKJQX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:FZERHIULMFGESH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:256.3013
Molecular Formula:C18H12N2
InChIKey:WPTCSQBWLUUYDV-UHFFFAOYSA-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:104.0615
Molecular Formula:C3H4O4
InChIKey:OFOBLEOULBTSOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:GTPZHMGXKZIHKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.2799
Molecular Formula:C16H13NO2
InChIKey:LQXGLEIJLFJYBE-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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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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:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:Not Available
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Compound Information
Molecular Weight:221.2539
Molecular Formula:C15H11NO
InChIKey:ORXSOQFSAQHWSR-UHFFFAOYSA-N
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:VEPYQCZRVLNDBC-KNVOCYPGSA-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:199.2054
Molecular Formula:C12H9NO2
InChIKey:OGYVBKHUIVJORN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:291.3438
Molecular Formula:C19H17NO2
InChIKey:NKTJXKSVVDCPJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.1467
Molecular Formula:C8H7NO2
InChIKey:IQYKXFGRHNUSPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:HXUIDZOMTRMIOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.1146
Molecular Formula:C5H7NO2
InChIKey:ZIUSEGSNTOUIPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:NXMFJCRMSDRXLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.709
Molecular Formula:C16H10ClNO2
InChIKey:UPAURWPZIYNCDE-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:245.3184
Molecular Formula:C18H15N
InChIKey:HIGDNPPZNMGDPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:QSJXEFYPDANLFS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.2839
Molecular Formula:C15H14N2O2
InChIKey:QRHCDLFYOBJDPA-CAOOACKPSA-N
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Compound Information
Molecular Weight:170.2105
Molecular Formula:C11H10N2
InChIKey:MVYNJRWXFSDRQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1298
Molecular Formula:C5H8N2O
InChIKey:MATJPVGBSAQWAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:CATSNJVOTSVZJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2319
Molecular Formula:C13H10N2
InChIKey:KFGUXZDBKCPVFY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:BNDRWEVUODOUDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:JDXYSCUOABNLIR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.1947
Molecular Formula:C11H9NO2
InChIKey:WXYKQNAKEPRCGF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2426
Molecular Formula:C14H10N2
InChIKey:YQZGQXPHGLAEHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.3917
Molecular Formula:C22H18N2
InChIKey:RWOUETIZGZHNKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:CLBGBMTXSMVRAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2637
Molecular Formula:C13H14N2
InChIKey:KSLDFJCPPSPBDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.2206
Molecular Formula:C12H11NO3
InChIKey:BQOSHNXSCBVHRZ-UKTHLTGXSA-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:168.1946
Molecular Formula:C11H8N2
InChIKey:FYIDOXAVHGPMLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.2539
Molecular Formula:C15H11NO
InChIKey:RCZOGESGQUHUFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2212
Molecular Formula:C12H11NO2
InChIKey:BAWCSYLGYDUKMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.1947
Molecular Formula:C11H9NO2
InChIKey:YFNDTCZARIEYNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:287.3105
Molecular Formula:C16H17NO4
InChIKey:VZHHMXOSTRYKCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:SLPUTJFVMJPMKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.245
Molecular Formula:C5H7NOS2
InChIKey:UPCYEFFISUGBRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.11
Molecular Formula:C6H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:WRQNANDWMGAFTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:SIKTVUHUQZNEPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1732
Molecular Formula:C9H8N2
InChIKey:GDJDODGBGRBEAN-TWGQIWQCSA-N
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Compound Information
Molecular Weight:261.2747
Molecular Formula:C17H11NO2
InChIKey:IQQAKYHPGYGTMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:SMWDFEZZVXVKRB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2512
Molecular Formula:C12H14N2O3
InChIKey:QZJNARADSLDZSV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.2161
Molecular Formula:C13H9NO2
InChIKey:FVRSZDRUQOAXGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.62
Molecular Formula:C9H9ClO2
InChIKey:MCRINSAETDOKDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:RZXMPPFPUUCRFN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YRKCREAYFQTBPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.351
Molecular Formula:C12H10N2S2
InChIKey:AQBHGKBUMYCQHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.2668
Molecular Formula:C15H12N2O4
InChIKey:RQHKVRJVDANATC-LZYBPNLTSA-N
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Compound Information
Molecular Weight:249.264
Molecular Formula:C16H11NO2
InChIKey:VXTYWQBVPQPTIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:GPRYKVSEZCQIHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2426
Molecular Formula:C14H10N2
InChIKey:TYVWGQYBWPFUKK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:DEDGUGJNLNLJSR-VURMDHGXSA-N
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Compound Information
Molecular Weight:318.778
Molecular Formula:C15H11ClN2O2S
InChIKey:QEHKDISMEUPIRR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.1708
Molecular Formula:C9H7N3O2
InChIKey:MRHKUOCXBIXEAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:273.2839
Molecular Formula:C15H15NO4
InChIKey:ICMBEQVDQPLOFB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:WLJVXDMOQOGPHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:FDPIMTJIUBPUKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:MAOBFOXLCJIFLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:OJVAMHKKJGICOG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.301
Molecular Formula:C15H17NO2
InChIKey:ODIGAONSIRFEDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:OWMJAQBUFVTERI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.0621
Molecular Formula:C3H4O3
InChIKey:LCTONWCANYUPML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.334
Molecular Formula:C15H12N2S
InChIKey:JIEIOYRQYUXNBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.1846
Molecular Formula:C10H9NO
InChIKey:APLVPBUBDFWWAD-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:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.2732
Molecular Formula:C14H14N2O2
InChIKey:PPMUTDCSFJUILM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.1846
Molecular Formula:C10H9NO
InChIKey:OMQWBTOTNRMKAK-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:141.1247
Molecular Formula:C6H7NO3
InChIKey:XGTZSVQFCSDHEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.164
Molecular Formula:C15H10BrN3
InChIKey:CXIKNGKRVYHVQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:CVBUKMMMRLOKQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.176
Molecular Formula:C8H10N2O4
InChIKey:MTUIWNVBJJHEQM-WAYWQWQTSA-N
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Compound Information
Molecular Weight:263.2906
Molecular Formula:C17H13NO2
InChIKey:UVIFCFBKDKJCFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2958
Molecular Formula:C16H14N2
InChIKey:BLXVPIDGZNQNGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:104.0648
Molecular Formula:C2H4N2O3
InChIKey:FYFYCAVDUPOEOO-HNQUOIGGSA-N
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Compound Information
Molecular Weight:143.1852
Molecular Formula:C10H9N
InChIKey:DTBDAFLSBDGPEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:Not Available
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Compound Information
Molecular Weight:230.264
Molecular Formula:C16H10N2
InChIKey:QHGZYCJXIVNYPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3221
Molecular Formula:C20H12N2O
InChIKey:RQXRPNUNRMIDMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:TYEYBOSBBBHJIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.2579
Molecular Formula:C14H13NO3
InChIKey:XMLJGUKMNZWJEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:NVPCGXUWUBHZBD-NSCUHMNNSA-N
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Compound Information
Molecular Weight:233.3077
Molecular Formula:C17H15N
InChIKey:DSMQRYGYUXRHRQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2206
Molecular Formula:C12H10N2O
InChIKey:FQSFHLUMNCPFJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-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:285.318
Molecular Formula:C15H11NO3S
InChIKey:KAFSOJAHZZSPFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1094
Molecular Formula:C6H6O4
InChIKey:VHILMKFSCRWWIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.227
Molecular Formula:C8H9NO3S
InChIKey:LKYNWTGTRVZBPA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.045
Molecular Formula:Na2S
InChIKey:GRVFOGOEDUUMBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:DCZFGQYXRKMVFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2045
Molecular Formula:C9H14O5
InChIKey:ZSANYRMTSBBUCA-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:165.1461
Molecular Formula:C8H7NO3
InChIKey:ARKIFHPFTHVKDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.0767
Molecular Formula:C3H5NO3
InChIKey:QCDJOJKIHZQJGX-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:226.2307
Molecular Formula:C13H10N2O2
InChIKey:VDYZZOFUDCMYHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:PAYRUJLWNCNPSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2117
Molecular Formula:C11H11N
InChIKey:WLWBKLRAHBGNIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:381.4281
Molecular Formula:C27H15N3
InChIKey:OYXPENCJHPYWHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.2555
Molecular Formula:C14H13NO7
InChIKey:HKAYCZZMQFSIFK-YHYXMXQVSA-N
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Compound Information
Molecular Weight:183.249
Molecular Formula:C13H13N
InChIKey:RXBYRTSOWREATF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.248
Molecular Formula:C10H9NO3S
InChIKey:DNFIRSKJJVJGLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.058
Molecular Formula:C8H7BrN2O
InChIKey:RMXWWJQHIWXRIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.1555
Molecular Formula:C9H5N3O
InChIKey:LSWOATMFSGNETB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:143.1852
Molecular Formula:C10H9N
InChIKey:SMUQFGGVLNAIOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:SHQSVMDWKBRBGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2637
Molecular Formula:C13H14N2
InChIKey:IDSANSILHACZQK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.2478
Molecular Formula:C13H13NO2
InChIKey:DUBPJEDOCJXVKG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:DYRDKSSFIWVSNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.3205
Molecular Formula:C17H15N3O
InChIKey:NHTNJVCDDAACQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.3544
Molecular Formula:C20H16N2
InChIKey:UQQWIVZGTAMRDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.1675
Molecular Formula:C10H7NO3
InChIKey:XOQQVKDBGLYPGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2426
Molecular Formula:C14H10N2
InChIKey:XAVCWNGDMHAGKP-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:373.4459
Molecular Formula:C27H19NO
InChIKey:PEFSRJQBFDQUDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2915
Molecular Formula:C14H17N
InChIKey:GMTGCIAJHZEUNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.212
Molecular Formula:C8H7NO2S
InChIKey:ZFCFFNGBCVAUDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SUSQOBVLVYHIEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2472
Molecular Formula:C13H12N2O
InChIKey:KBJYSSJAVZUXTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.0728
Molecular Formula:C4H4O3
InChIKey:JCGNDDUYTRNOFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2915
Molecular Formula:C14H17N
InChIKey:DWDMKPMAMRQPAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.129
Molecular Formula:C8H5NO5
InChIKey:NRZWECORTTWSEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.1739
Molecular Formula:C9H9NO
InChIKey:OZXSEERUQXBNLB-WTDSWWLTSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:GTDQGKWDWVUKTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:MAOBFOXLCJIFLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.1739
Molecular Formula:C9H9NO
InChIKey:ZSZKASWGDFWFOQ-HWKANZROSA-N
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Compound Information
Molecular Weight:137.135
Molecular Formula:C3H6O4S
InChIKey:ZYKVCFGIFGTEPR-UHFFFAOYSA-M
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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:233.2646
Molecular Formula:C16H11NO
InChIKey:FBFLIZGARFAIRP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:TVKMRMXVNWHKTF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.3496
Molecular Formula:C18H19NO
InChIKey:UICNNPDZLGFJRO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:311.766
Molecular Formula:C17H14ClN3O
InChIKey:LIOWYHNSKFLUIT-RGVLZGJSSA-N
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Compound Information
Molecular Weight:307.3432
Molecular Formula:C19H17NO3
InChIKey:QWBMQDLOOLTKOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.4556
Molecular Formula:C25H22N2
InChIKey:PCHPNTZMYFVIEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.3172
Molecular Formula:C18H15NO2
InChIKey:IWUNBLHFLWOSBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.2983
Molecular Formula:C18H12N2O5
InChIKey:GMGQCIKXHVVHCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.684
Molecular Formula:C9H9ClO3S
InChIKey:BRDBHPZILGTBFY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.162
Molecular Formula:C8H9NO3
InChIKey:KLVJSCPAICGHBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.3432
Molecular Formula:C19H17NO3
InChIKey:IOZQKLROTNQIOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.36
Molecular Formula:C16H14N2O2S
InChIKey:SRVSOPAGFZARNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:327.397
Molecular Formula:C18H17NO3S
InChIKey:QQIZJRDUQSHBRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:422.902
Molecular Formula:C19H15ClO5S2
InChIKey:VUJGSGFLRXLZIG-UHFFFAOYSA-N
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