Standard Article

Reduction with Diimide

  1. Daniel J. Pasto1,
  2. Richard T. Taylor2

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or040.02

Organic Reactions

Organic Reactions

How to Cite

Pasto, D. J. and Taylor, R. T. 2004. Reduction with Diimide. Organic Reactions. 40:2:91–155.

Author Information

  1. 1

    University of Notre Dame, Notre Dame, Indiana

  2. 2

    Miami University, Oxford, Ohio

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

The reduction of a double bond in the presence of hydrazine appears to have been first observed in 1905 during the reaction of glyceryl oleate, which produced stearic hydrazide. That hydrazine could act as a reagent for the reduction of a carbon[BOND]carbon double bond was firmly established much later, at which point it was shown that oleic acid could be reduced to stearic acid by treatment with hydrazine, or with hydrazine and sulfur. In 1941 it was reported that vinyl groups in chlorins and porphyrins are selectively reduced to ethyl groups by hydrazine under mild conditions. The synthetic potential of this type of reduction was not recognized until the early 1960s when results from several independent laboratories implicated diimide (HN[DOUBLE BOND]NH) as the actual reducing agent.

Evidence for the existence of diimide (diimine and diazene) was first obtained in 1892 in the decarboxylation of dipotassium azodicarboxylate, which produced equimolar quantities of nitrogen and hydrazine by the proposed disproportionation of diimide. In 1910 it was proposed that diimide was formed in the reaction of benzenesulfonylhydrazide with hot alkali. Following the proposal that diimide is the reactive intermediate in these reduction reactions, numerous experimental and theoretical studies were launched to find other methods for the synthesis of diimide and to determine the structure(s) of the reactive intermediate(s) and the mechanism of the reduction reaction. An excellent review has appeared which covers the literature on the structure and molecular properties, spectral characterization, and gas-phase reactions of diimide. In this chapter only highlights of such areas are covered. Two reviews covering reductions with diimide appeared in 1965, but none since that time. Most organic texts describe diimide reductions, but not in significant detail.

There are three potential structures for diimide: cis- and trans-diimide and 1,1-diimide (aminonitrene).

trans-Diimide can be generated and trapped at low temperature by a gas-phase electric discharge in hydrazine and by the thermal decomposition of metal salts of p-toluenesulfonylhydrazide. Recently, 1,1-diimide has been generated and trapped by the low temperature photochemical decomposition of carbamoyl azide. Although cis-diimide must be formed as a reactive intermediate in many systems, it has not yet been unambiguously characterized.

The diimide system has been subjected to several theoretical studies at many different basis set levels.

The results of stereochemical studies on the reduction of alkenes and alkynes have led to the suggestion that cis-diimide is the reactive hydrogen-transfer reagent. These results support the suggestion that cis-diimide is the active hydrogen-transfer reagent. The fact that cis-diimide has not been observed and that the calculated inversion and rotation barriers are too large to provide a rate of isomerization of trans- to cis-diimide that would be sufficiently high to account for the observed rate of reduction provides for a mechanistic dilemma. In gas-phase reactions isomerization of trans- to cis-diimide has been proposed to be the rate-limiting step. In solution, however, the isomerization in all probability occurs via a catalyzed process, probably involving a rapid protonation–deprotonation sequence. In this chapter the use of the term “diimide” implies cis-diimide as the reducing agent.

The energy barriers for the disproportionation of cis- with cis-, and cis- with trans-diimide are calculated to be 19.3 and 23.8 kcal per mole, considerably smaller than the barriers for hydrogen transfer to a carbon[BOND]carbon double bond. From a practical point of view, this competing disproportionation requires the use of considerable excesses of the diimide precursors in the reduction reactions.

Keywords:

  • reduction;
  • diimide;
  • mechanism;
  • substitution;
  • relative reactivity;
  • stereoselectivity;
  • alkenes;
  • dienes;
  • unsaturated acids;
  • scope;
  • limitations;
  • experimental procedures;
  • method comparisons;
  • alkynes;
  • allenes;
  • carbonyl compounds;
  • imines;
  • hydrazones;
  • azo compounds;
  • substituted compounds

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:UAEPNZWRGJTJPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.037
Molecular Formula:C8H10Br2O2S
InChIKey:GVCCYCIGPUUNOH-RYVOCIFZSA-N
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Compound Information
Molecular Weight:177.2258
Molecular Formula:C8H15NO3
InChIKey:Not Available
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Compound Information
Molecular Weight:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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Molecular Weight:183.1183
Molecular Formula:C7H5NO5
InChIKey:LWOWNIPZHGWKNR-DUXPYHPUSA-N
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Compound Information
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:BOVQCIDBZXNFEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.088
Molecular Formula:C4H6O4
InChIKey:KDYFGRWQOYBRFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:SRXBXRUSSXXHKB-OLQVQODUSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:RRKODOZNUZCUBN-CCAGOZQPSA-N
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Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:FERIUCNNQQJTOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:KHFWLADMBPVICJ-OLQVQODUSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:LRHPLDYGYMQRHN-UHFFFAOYSA-N
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Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:WSWCOQWTEOXDQX-MQQKCMAXSA-N
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Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:XXNKHBFCIGOWEC-KNVOCYPGSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:YFRMDUCSDQJTKP-SNAWJCMRSA-N
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Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:UHYCVZPDIIKYRO-PHDIDXHHSA-N
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Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:OPKSUXHYTUKXGR-ALCCZGGFSA-N
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Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:JMMZCWZIJXAGKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.1937
Molecular Formula:C8H13NO3
InChIKey:PDJDHXDKFNTNOK-SNAWJCMRSA-N
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Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:SUGCEFZIYJHZAA-OLQVQODUSA-N
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Compound Information
Molecular Weight:185.061
Molecular Formula:C8H9Br
InChIKey:URFPRAHGGBYNPW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.2287
Molecular Formula:C8H16O2
InChIKey:Not Available
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Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:SBZXBUIDTXKZTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.0987
Molecular Formula:C5H6O4
InChIKey:LVHBHZANLOWSRM-UHFFFAOYSA-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:110.1968
Molecular Formula:C8H14
InChIKey:GPRLTFBKWDERLU-OCAPTIKFSA-N
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Compound Information
Molecular Weight:60.095
Molecular Formula:C3H8O
InChIKey:BDERNNFJNOPAEC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:KTZVZZJJVJQZHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:OFBQJSOFQDEBGM-UHFFFAOYSA-N
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Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:LKNKAJUDGBRRBI-KNVOCYPGSA-N
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Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:CGKPQMCLTLUAOW-UHFFFAOYSA-N
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Molecular Weight:181.103
Molecular Formula:C8H14Cl2
InChIKey:CXYRLCVPPVQCSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:FWZUNOYOVVKUNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:Not Available
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Molecular Weight:130.0987
Molecular Formula:C5H6O4
InChIKey:PSALGRFLQMWHPH-IUYQGCFVSA-N
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Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:HIZVCIIORGCREW-UHFFFAOYSA-N
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Molecular Weight:185.061
Molecular Formula:C8H9Br
InChIKey:WMPPDTMATNBGJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.166
Molecular Formula:C7H10O
InChIKey:Not Available
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Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:ATQUFXWBVZUTKO-UHFFFAOYSA-N
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Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:NTIZESTWPVYFNL-UHFFFAOYSA-N
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Molecular Weight:182.2
Molecular Formula:C7H6N2O2S
InChIKey:NRCAMRMJWDLFBZ-SYDPRGILSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:DKLGHTDQIGTELY-QYNIQEEDSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:SDJHPPZKZZWAKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:AOLWVFLQJQUFMW-QYNIQEEDSA-N
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Compound Information
Molecular Weight:128.1259
Molecular Formula:C6H8O3
InChIKey:HDRUBHQNIALXHQ-OLQVQODUSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:92.1333
Molecular Formula:C4H10O2
InChIKey:Not Available
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Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:BUDQDWGNQVEFAC-UHFFFAOYSA-N
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Molecular Weight:151.1626
Molecular Formula:C8H9NO2
InChIKey:RESTWAHJFMZUIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:DMEGYFMYUHOHGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:SHEFDRYFQPAXGP-KVFPUHGPSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:CTMHWPIWNRWQEG-UHFFFAOYSA-N
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Molecular Weight:122.992
Molecular Formula:C3H7Br
InChIKey:CYNYIHKIEHGYOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.0829
Molecular Formula:C5H4O4
InChIKey:VRICAAGEANIOQC-IUYQGCFVSA-N
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Compound Information
Molecular Weight:183.045
Molecular Formula:C8H7Br
InChIKey:YMOONIIMQBGTDU-SREVYHEPSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:WWUVJRULCWHUSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:Not Available
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:Not Available
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Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:QSAWQNUELGIYBC-OLQVQODUSA-N
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Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:KWSARSUDWPZTFF-CSMHCCOUSA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:UYIGPXCIFJZRJL-RQJHMYQMSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:CTLSARLLLBZBRV-OLQVQODUSA-N
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Molecular Weight:30.069
Molecular Formula:C2H6
InChIKey:OTMSDBZUPAUEDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.1259
Molecular Formula:C6H8O3
InChIKey:RQPLOKGXDBKIMG-GUCUJZIJSA-N
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Compound Information
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:QMMOXUPEWRXHJS-HYXAFXHYSA-N
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Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:RIICRLQIUAAOOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:OKJQSUPURXTNME-UHFFFAOYSA-N
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Molecular Weight:176.2067
Molecular Formula:C8H14O4
InChIKey:Not Available
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Molecular Weight:98.0999
Molecular Formula:C5H6O2
InChIKey:KELINLLZZFLEQJ-SYDPRGILSA-N
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Molecular Weight:179.087
Molecular Formula:C8H12Cl2
InChIKey:LUWLLVYQLSHGGK-WAYWQWQTSA-N
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Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:ZFFMLCVRJBZUDZ-UHFFFAOYSA-N
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Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:MNEHGPASSFGNGC-OCAPTIKFSA-N
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Compound Information
Molecular Weight:116.138
Molecular Formula:C4H4O2S
InChIKey:YNTZSHZRQQLDNQ-ZXZARUISSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:Not Available
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Molecular Weight:136.214
Molecular Formula:C8H8S
InChIKey:GMPDOIGGGXSAPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:GWYPDXLJACEENP-UHFFFAOYSA-N
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Molecular Weight:116.0722
Molecular Formula:C4H4O4
InChIKey:VZCYOOQTPOCHFL-UPHRSURJSA-N
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Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:Not Available
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Molecular Weight:170.1626
Molecular Formula:C8H10O4
InChIKey:ILUAAIDVFMVTAU-OLQVQODUSA-N
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Compound Information
Molecular Weight:20.0276
Molecular Formula:H2O
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:183.045
Molecular Formula:C8H7Br
InChIKey:WGGLDBIZIQMEGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.1342
Molecular Formula:C7H7NO5
InChIKey:YOYKRMULSQTSIS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:YBSKNHJJHGWNAS-CRCLSJGQSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:AJQVASAUQUTVJK-YUMQZZPRSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:YKRVEGFRYRZTEY-KVSKUHBBSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:YULMNMJFAZWLLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.0944
Molecular Formula:C3H8O2
InChIKey:XNWFRZJHXBZDAG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:DHXVGJBLRPWPCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:Not Available
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Compound Information
Molecular Weight:98.0569
Molecular Formula:C4H2O3
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:YWAKXRMUMFPDSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.23
Molecular Formula:C8H10S
InChIKey:AEHWKBXBXYNPCX-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:86.1718
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:ZNQVEEAIQZEUHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:IWDGMFDVSXRQHQ-KVFPUHGPSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:WJTCGQSWYFHTAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:IJJCLEUIIWDFDI-KVFPUHGPSA-N
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Compound Information
Molecular Weight:96.1666
Molecular Formula:C7H10
InChIKey:Not Available
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Compound Information
Molecular Weight:150.305
Molecular Formula:C6H14S2
InChIKey:ALVPFGSHPUPROW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:YKYONYBAUNKHLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.602
Molecular Formula:C8H9Cl
InChIKey:VWRYIVVPJBZDNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:MHLPKAGDPWUOOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:SJYNFBVQFBRSIB-KNVOCYPGSA-N
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Compound Information
Molecular Weight:62.0678
Molecular Formula:C2H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:LPIQUOYDBNQMRZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:QWTDNUCVQCZILF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:NNGVLPJYESSKNP-ALCCZGGFSA-N
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Compound Information
Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:ZSWFCLXCOIISFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.216
Molecular Formula:C7H8N2O2S
InChIKey:CUXXAKSMSKUBDW-SYDPRGILSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:XXROGKLTLUQVRX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:RIRARCHMRDHZAR-RNFRBKRXSA-N
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Compound Information
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:KWYHDKDOAIKMQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:UIERETOOQGIECD-ONEGZZNKSA-N
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:DKMROQRQHGEIOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:GHVNFZFCNZKVNT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:FNOOZJAPZFHNCW-RQJHMYQMSA-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:128.212
Molecular Formula:C8H16O
InChIKey:MFVJXTZKDXQYDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.11
Molecular Formula:C6H6O3
InChIKey:JOJNGMNGLCNAMS-GUCUJZIJSA-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:114.0993
Molecular Formula:C5H6O3
InChIKey:HALJZYJCZSWUGL-CRCLSJGQSA-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:140.61
Molecular Formula:C8H9Cl
InChIKey:GPOFSFLJOIAMSA-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:149.1467
Molecular Formula:C8H7NO2
InChIKey:YFZHODLXYNDBSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:GDOPTJXRTPNYNR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WCASXYBKJHWFMY-NSCUHMNNSA-N
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Compound Information
Molecular Weight:148.1535
Molecular Formula:C6H10O4
InChIKey:Not Available
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Compound Information
Molecular Weight:130.0987
Molecular Formula:C5H8O4
InChIKey:WXUAQHNMJWJLTG-UHFFFAOYSA-L
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Compound Information
Molecular Weight:118.154
Molecular Formula:C4H6O2S
InChIKey:IIBZFEQTESDEJY-ZXZARUISSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:Not Available
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:YNQLUTRBYVCPMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:332.053
Molecular Formula:C8H12Br2O2S
InChIKey:RFFHTJJMSBLMPU-RYVOCIFZSA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:VRAVGRTWSITEDR-UMRXKNAASA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:VIQRCOQXIHFJND-OCAPTIKFSA-N
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:BYPTYAZTGAQPGR-OLQVQODUSA-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:80.1277
Molecular Formula:C6H8
InChIKey:AIGOAHIDIXDVAT-VMAMZZGPSA-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:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-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:124.1372
Molecular Formula:C7H8O2
InChIKey:HYYSOJRIVSFYTG-RQJHMYQMSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:OCMAMJALARSQKS-RNLVFQAGSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:HEIQYFOEXLSSCE-RZVDLVGDSA-N
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:SSTJIHZNVIHGPJ-UMRXKNAASA-N
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:UATLJEJMCNCMGA-KNVOCYPGSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:DBUJFULDVAZULB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:WKPCMVVDNLHTCP-UCUVTLDDSA-N
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Compound Information
Molecular Weight:116.1942
Molecular Formula:C7H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:YZLCEXRVQZNGEK-OLQVQODUSA-N
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Compound Information
Molecular Weight:146.274
Molecular Formula:C6H10S2
InChIKey:PFRGXCVKLLPLIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:RGSFGYAAUTVSQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:SHOJXDKTYKFBRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.2085
Molecular Formula:C8H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:28.0532
Molecular Formula:C2H4
InChIKey:Not Available
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Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:CGBYBGVMDAPUIH-ARJAWSKDSA-N
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Compound Information
Molecular Weight:61.0831
Molecular Formula:C2H7NO
InChIKey:HZAXFHJVJLSVMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.2085
Molecular Formula:C8H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:UMRZSTCPUPJPOJ-KNVOCYPGSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:KEXYAVHJBNJUCG-GJMOJQLCSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:XKPWDSUJWUMCPD-KNVOCYPGSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:MPTIIWHIYWEJQR-UCUVTLDDSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:BDJSZICOAPUZNY-WAYWQWQTSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:RNFXAEBUWFIOQW-SYDPRGILSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:WWZKQHOCKIZLMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.0728
Molecular Formula:C4H4O3
InChIKey:Not Available
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:DHEXQYPNAZKWFS-DUXPYHPUSA-N
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Compound Information
Molecular Weight:63.545
Molecular Formula:Cu
InChIKey:JPVYNHNXODAKFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:30.0293
Molecular Formula:H2N2
InChIKey:RAABOESOVLLHRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YYPNJNDODFVZLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:RRHGJUQNOFWUDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:GRPFSWFCSGHVIB-OCAPTIKFSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:120.1004
Molecular Formula:C4H6O4
InChIKey:Not Available
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Compound Information
Molecular Weight:32.0416
Molecular Formula:H2N2
InChIKey:Not Available
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Compound Information
Molecular Weight:116.0722
Molecular Formula:C4H4O4
InChIKey:VZCYOOQTPOCHFL-OWOJBTEDSA-N
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Compound Information
Molecular Weight:130.0987
Molecular Formula:C5H6O4
InChIKey:LVHBHZANLOWSRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:QMMOXUPEWRXHJS-HWKANZROSA-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:78.1118
Molecular Formula:C6H6
InChIKey:VMQPMGHYRISRHO-VMAMZZGPSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UVJHQYIOXKWHFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:AHUADBUKFJZUTM-OLQVQODUSA-N
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Compound Information
Molecular Weight:116.1547
Molecular Formula:C6H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:61.0581
Molecular Formula:C2H4O2
InChIKey:Not Available
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Compound Information
Molecular Weight:33.048
Molecular Formula:CH4O
InChIKey:Not Available
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Compound Information
Molecular Weight:100.1948
Molecular Formula:C7H12
InChIKey:Not Available
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:JFNLZVQOOSMTJK-KNVOCYPGSA-N
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Compound Information
Molecular Weight:98.1825
Molecular Formula:C7H12
InChIKey:Not Available
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:RIRARCHMRDHZAR-KNVOCYPGSA-N
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Compound Information
Molecular Weight:183.045
Molecular Formula:C8H7Br
InChIKey:YMOONIIMQBGTDU-VOTSOKGWSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:HEIQYFOEXLSSCE-RZVDLVGDSA-N
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Compound Information
Molecular Weight:47.0746
Molecular Formula:C2H6O
InChIKey:Not Available
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:DNZZPKYSGRTNGK-PQZOIKATSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:Not Available
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Compound Information
Molecular Weight:114.225
Molecular Formula:C8H16
InChIKey:Not Available
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:OCMAMJALARSQKS-JIGDXULJSA-N
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Compound Information
Molecular Weight:128.2085
Molecular Formula:C8H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:62.0601
Molecular Formula:C2H4O2
InChIKey:Not Available
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:AGYFZLKAMGTDRK-SOKYHKBVSA-N
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Compound Information
Molecular Weight:182.604
Molecular Formula:C9H7ClO2
InChIKey:GXLIFJYFGMHYDY-UTCJRWHESA-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:150.2606
Molecular Formula:C11H18
InChIKey:XGGMOGVCOVLFGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.2285
Molecular Formula:C8H18
InChIKey:UWNADWZGEHDQAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:VUWMEDZMVLUYQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2237
Molecular Formula:C12H12
InChIKey:JOUWPBDYKVWGGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.352
Molecular Formula:C14H16O4S
InChIKey:Not Available
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Compound Information
Molecular Weight:210.2711
Molecular Formula:C15H14O
InChIKey:MYSWSYIZGBJZFN-NWQDQBDJSA-N
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Compound Information
Molecular Weight:156.2186
Molecular Formula:C9H14O2
InChIKey:Not Available
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:GYNNXHKOJHMOHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.2392
Molecular Formula:C9H18
InChIKey:POCNHGFJLGYFIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:MCIIDRLDHRQKPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:FRPZMMHWLSIFAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:ZLCSFXXPPANWQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:WCMSFBRREKZZFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:LDRWCUVIIYASKR-DTORHVGOSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:BESIOWGPXPAVOS-UPHRSURJSA-N
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Compound Information
Molecular Weight:238.2796
Molecular Formula:C13H18O4
InChIKey:XXYNRGOETHAVTI-NSHDSACASA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:DSNYFFJTZPIKFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:OEWLMENOMYPGDY-KXNHARMFSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-UPHRSURJSA-N
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Compound Information
Molecular Weight:194.3562
Molecular Formula:C14H26
InChIKey:SQXVLOWLOJUUGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:NGSMAXPULGPQNT-PRLRHMMRSA-N
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Compound Information
Molecular Weight:256.96
Molecular Formula:C10H18Sn
InChIKey:OGSMSQSDBBCTNY-NOTWHITJSA-N
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Compound Information
Molecular Weight:186.2927
Molecular Formula:C14H18
InChIKey:NQGKKPHSLSIBRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.3297
Molecular Formula:C13H24
InChIKey:PDZIHQLAPPHQKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.241
Molecular Formula:C9H10S
InChIKey:Not Available
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Compound Information
Molecular Weight:152.2729
Molecular Formula:C11H18
InChIKey:Not Available
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Compound Information
Molecular Weight:166.3031
Molecular Formula:C12H22
InChIKey:VTPJFHQPYSSSCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:VKXPWBQDIDSWCA-JGVFFNPUSA-N
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Compound Information
Molecular Weight:140.2658
Molecular Formula:C10H20
InChIKey:XTVMZZBLCLWBPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:WBYWAXJHAXSJNI-SREVYHEPSA-N
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Compound Information
Molecular Weight:162.2713
Molecular Formula:C12H18
InChIKey:JYICFGQGKUQFQQ-DTIDVZRVSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2765
Molecular Formula:C11H20
InChIKey:UWBJPUXTTHBACI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.2392
Molecular Formula:C9H18
InChIKey:GPTJTTCOVDDHER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.3031
Molecular Formula:C12H22
InChIKey:HYPABJGVBDSCIT-UPHRSURJSA-N
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Compound Information
Molecular Weight:133.1903
Molecular Formula:C9H11N
InChIKey:LQFLWKPCQITJIH-UHFFFAOYSA-N
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