Standard Article

Intermolecular C–H Insertions of Carbenoids

  1. Huw M. L. Davies1,
  2. Phillip M. Pelphrey2

Published Online: 16 DEC 2011

DOI: 10.1002/0471264180.or075.02

Organic Reactions

Organic Reactions

How to Cite

Davies, H. M. L. and Pelphrey, P. M. 2011. Intermolecular C–H Insertions of Carbenoids. Organic Reactions. 75:2:75–212.

Author Information

  1. 1

    Emory University, Department of Chemistry, Atlanta, Georgia

  2. 2

    Texas Wesleyan University, Department of Chemistry, Fort Worth, Texas

Publication History

  1. Published Online: 16 DEC 2011

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Abstract

The metal-catalyzed reactions of diazo compounds have broad utility in organic synthesis. The resulting high-energy metal carbenoid intermediates are capable of a range of useful transformations, including cyclopropanation, ylide formation, and C-H insertion.

The intermolecular C-H insertion by metal carbenoids is the most versatile reaction to date for stereoselective C-H functionalization. This chapter covers the historical background of C-H insertions and describes how the utilization of new catalysts and more stabilized carbenoids has resulted in major advances in the field. Now that highly diastereoselective and enantioselective C-H functionalization can be achieved, the method can be effectively applied to the synthesis of pharmaceutical agents and natural products. This chapter focuses exclusively on intermolecular C-H insertions of metal carbenoids in sp3-hybridized C-H bonds. The carbenoids can be classified into three major classes: 1, acceptor-substituted carbenoids; 2, acceptor/acceptor-substituted carbenoids; and 3, donor/acceptor-substituted carbenoids

Keywords:

  • Intermolecular C-H insertions;
  • Carbenoids;
  • Hydrocarbons;
  • Activated C-H bonds;
  • Site selectivity;
  • Donors;
  • Acceptors;
  • Aryldiazoacetates;
  • Metal catalysts;
  • Experimental procedures;
  • Mechanisms

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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:184.2753
Molecular Formula:C11H20O2
InChIKey:NRVPMFHPHGBQLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.816
Molecular Formula:C14H27ClO2
InChIKey:ZRDKEGOCDGXXTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.4027
Molecular Formula:C12H24O3Si
InChIKey:QOKSTPAXPRLTHJ-BQYQJAHWSA-N
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Compound Information
Molecular Weight:340.5836
Molecular Formula:C22H44O2
InChIKey:OJLCPVMTNVZTMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:269.3383
Molecular Formula:C17H19NO2
InChIKey:NHOGTKAKJAXBLQ-CVEARBPZSA-N
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Compound Information
Molecular Weight:328.202
Molecular Formula:C14H18BrNO3
InChIKey:SHQYTANSTMUDNS-FRRDWIJNSA-N
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Compound Information
Molecular Weight:467.5556
Molecular Formula:C30H29NO4
InChIKey:KVOLRKBIXNHPNV-PUHABZHSSA-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:206.71
Molecular Formula:C10H19ClO2
InChIKey:NSGLAUWLFIRCHX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.763
Molecular Formula:C12H23ClO2
InChIKey:GTKQAXQUIOBEBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.2609
Molecular Formula:C6H14Si
InChIKey:KDQBKCRYCZJUAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1121
Molecular Formula:C5H6N2O4
InChIKey:UFAZHCVBGMSJHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:382.5234
Molecular Formula:C19H30O6Si
InChIKey:QFIIMWKHMFYRGY-RHIXDFSFSA-N
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Compound Information
Molecular Weight:173.2527
Molecular Formula:C9H19NO2
InChIKey:KIBNOUXOGRLBQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.1222
Molecular Formula:C4H10
InChIKey:NNPPMTNAJDCUHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2265
Molecular Formula:C11H14O4
InChIKey:CVGKRYANFUXZSV-SNVBAGLBSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:DTLRDIWEWLSXID-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:JMMZCWZIJXAGKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:QDMVBHCMOQVJTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.2796
Molecular Formula:C13H17NO2
InChIKey:IDFZQTFWJZUVDF-RYUDHWBXSA-N
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Compound Information
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:BPDOOLBDMQEYSL-OLZOCXBDSA-N
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Compound Information
Molecular Weight:159.609
Molecular Formula:CuO4S
InChIKey:ARUVKPQLZAKDPS-UHFFFAOYSA-L
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Compound Information
Molecular Weight:128.2874
Molecular Formula:C7H16Si
InChIKey:VPVXTYYXTKCTPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.127
Molecular Formula:C13H9BrN2O2
InChIKey:HVTMBWDJTNTDLA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.3236
Molecular Formula:C17H18O2
InChIKey:UOYZKGDHEXAIDE-GNXJLENFSA-N
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Compound Information
Molecular Weight:239.3107
Molecular Formula:C13H21NO3
InChIKey:WXKJZYNPICHKHB-OKLGRODASA-N
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Compound Information
Molecular Weight:298.4931
Molecular Formula:C16H30O3Si
InChIKey:ZOLKUQHPBACEQU-IVOOMUPKSA-N
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Compound Information
Molecular Weight:106.594
Molecular Formula:C5H11Cl
InChIKey:SQCZQTSHSZLZIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.2592
Molecular Formula:C14H14O3
InChIKey:COLZRWHDMATJTL-CYBMUJFWSA-N
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Compound Information
Molecular Weight:367.4382
Molecular Formula:C22H25NO4
InChIKey:BJFPSWMJANGPBP-YRPNKDGESA-N
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Compound Information
Molecular Weight:270.323
Molecular Formula:C17H18O3
InChIKey:GQWJOPZVVNVCAY-CVEARBPZSA-N
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Compound Information
Molecular Weight:901.022
Molecular Formula:C21H12AgBF18N8O4
InChIKey:FHEZJIGOZWKNRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:UUDHDPMXVFYWQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3501
Molecular Formula:C10H20O2Si
InChIKey:NFDMGUMNWMCTBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:HMMHDMNHBCSFFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.763
Molecular Formula:C12H23ClO2
InChIKey:RSQIRRTYOPSHQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:VUOGVGBBHBPFGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.4412
Molecular Formula:C16H34
InChIKey:DCAYPVUWAIABOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:KPBWNINPDIFOLJ-LLVKDONJSA-N
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Compound Information
Molecular Weight:199.2469
Molecular Formula:C10H17NO3
InChIKey:ROUYFJUVMYHXFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:IDSOAAMERORDNF-CQSZACIVSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:YYZUSRORWSJGET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:Not Available
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:ZIEQEHQHRQIHQB-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:200.3178
Molecular Formula:C12H24O2
InChIKey:SNNMLOUDFGQPSI-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:356.0701
Molecular Formula:C8H22O2Rh2
InChIKey:HDHWOFLAGAXEMG-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:100.2019
Molecular Formula:C7H16
InChIKey:BZHMBWZPUJHVEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:SJTYSQUKMOHFHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:ODBPUDIQDAAIJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:ABKUJXGRDNEJLQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:347.246
Molecular Formula:C18H19BrO2
InChIKey:ZLVUSIOQCOQRSV-MRXNPFEDSA-N
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Compound Information
Molecular Weight:186.2912
Molecular Formula:C11H22O2
InChIKey:KXQSCRLVFVDYQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.2631
Molecular Formula:C13H16O5
InChIKey:ISQIDFDTEUNGCN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:WTQUBDWSROKVEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.4772
Molecular Formula:C18H36O2
InChIKey:XIRNKXNNONJFQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.3648
Molecular Formula:C18H21NO2
InChIKey:DNRNSIJBSCBESJ-IAGOWNOFSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:CRZQGDNQQAALAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.2817
Molecular Formula:C10H22
InChIKey:DIOQZVSQGTUSAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:RGXWDWUGBIJHDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.583
Molecular Formula:C7H7Cl
InChIKey:Not Available
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Compound Information
Molecular Weight:574.301
Molecular Formula:C27H26Br2O4
InChIKey:AKZKBWFUDUOCPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:LQBZMLRJLRSDNW-ONEGZZNKSA-N
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Compound Information
Molecular Weight:96.106
Molecular Formula:CH4O3S
InChIKey:AFVFQIVMOAPDHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.762
Molecular Formula:C10H14CuO4
InChIKey:QYJPSWYYEKYVEJ-FDGPNNRMSA-L
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Compound Information
Molecular Weight:265.2619
Molecular Formula:C13H15NO5
InChIKey:SUDRWPLQOVWPGG-NEPJUHHUSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:UCQSHXPLTBHNLH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:OXMIDRBAFOEOQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.3869
Molecular Formula:C20H22O3
InChIKey:KIORSFXMPBGCJF-MOPGFXCFSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:ZFFMLCVRJBZUDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:JGHZJRVDZXSNKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:DUVBLOGROFWTDX-SNVBAGLBSA-N
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Compound Information
Molecular Weight:238.2796
Molecular Formula:C13H18O4
InChIKey:PHAMSSONVHXAAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:348.234
Molecular Formula:C17H18BrNO2
InChIKey:DLGZXSONAYGASX-MRXNPFEDSA-N
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Compound Information
Molecular Weight:264.4338
Molecular Formula:C12H28O4Si
InChIKey:ZUEKXCXHTXJYAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:313.187
Molecular Formula:C14H17BrO3
InChIKey:ISNLZFSINIBNAC-QITAHTHBSA-N
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Compound Information
Molecular Weight:255.068
Molecular Formula:C9H7BrN2O2
InChIKey:KAWBXRZMMASSLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2747
Molecular Formula:C11H19NO
InChIKey:IQSAPMJJUOSLOX-XXQWGACESA-N
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Compound Information
Molecular Weight:587.821
Molecular Formula:C35H45NO5Si
InChIKey:XMXAFKSVPWHAFU-UPHHSBJESA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:TVQGDYNRXLTQAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.5836
Molecular Formula:C22H44O2
InChIKey:XALTWFFDSODZHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:Not Available
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Compound Information
Molecular Weight:238.2796
Molecular Formula:C13H18O4
InChIKey:FNMYSNAXRXSTSC-GFCCVEGCSA-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:88.1482
Molecular Formula:C5H12O
InChIKey:CXBDYQVECUFKRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.1696
Molecular Formula:C9H7N3O4
InChIKey:UELGUGFAWDJOEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.203
Molecular Formula:C14H19BrO2
InChIKey:FUWKYDSJBQHYQA-GFCCVEGCSA-N
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Compound Information
Molecular Weight:174.2374
Molecular Formula:C9H18O3
InChIKey:GIRSHSVIZQASRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:RDOXTESZEPMUJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.3383
Molecular Formula:C17H20O4
InChIKey:BSDVNPLGXXWQCO-MRXNPFEDSA-N
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Compound Information
Molecular Weight:234.763
Molecular Formula:C12H23ClO2
InChIKey:FAPMBNKAEJVBLA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.682
Molecular Formula:C12H13ClO4
InChIKey:RLNNNKFPXSLQAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:MMLWYWOIAWZEFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:326.186
Molecular Formula:C14H16BrNO3
InChIKey:DXEUCTNIZHTWFG-OLZOCXBDSA-N
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Compound Information
Molecular Weight:324.233
Molecular Formula:C10H7F3N2O5S
InChIKey:ZQFRBKMXRWZIFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.3327
Molecular Formula:C15H21NO2
InChIKey:WJZNCJIOIACDBR-KBPBESRZSA-N
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Compound Information
Molecular Weight:434.6426
Molecular Formula:C27H34O3Si
InChIKey:KIGYOLZWCCCPTM-NWANREDQSA-N
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Compound Information
Molecular Weight:228.3709
Molecular Formula:C14H28O2
InChIKey:LHZUQCRRESCECT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.683
Molecular Formula:C9H17ClO2
InChIKey:MWXJXXQGWBPRSH-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:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:KPDQCPSAUOZDEW-CYBMUJFWSA-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:621.015
Molecular Formula:C15H3BF18N6
InChIKey:HVFPYJSKQLPQIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.51
Molecular Formula:C4H6O4Pd
InChIKey:YJVFFLUZDVXJQI-UHFFFAOYSA-L
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:MVFYGDOEVXKSNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:356.4861
Molecular Formula:C17H28O6Si
InChIKey:MJTAFXVTQWJELM-HOCLYGCPSA-N
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Compound Information
Molecular Weight:262.816
Molecular Formula:C14H27ClO2
InChIKey:HGGHZSFEHDIAIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.71
Molecular Formula:C10H19ClO2
InChIKey:OXBCEBCQYRUXEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:496.626
Molecular Formula:C23H36N2O8Si
InChIKey:VNTDVGRQIREHGX-OIISXLGYSA-N
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Compound Information
Molecular Weight:208.3275
Molecular Formula:C8H20O4Si
InChIKey:BOTDANWDWHJENH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:337.251
Molecular Formula:C17H21BrO2
InChIKey:HCWLGZAEENSBMB-ZBFHGGJFSA-N
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Compound Information
Molecular Weight:428.1327
Molecular Formula:C11H26O4Rh2
InChIKey:GIUSGMZFVRDWIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.198
Molecular Formula:C10H10N2O3
InChIKey:QPANVWVELCPKHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2265
Molecular Formula:C11H14O4
InChIKey:AHHVJNNIKJDUNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.388
Molecular Formula:C14H30
InChIKey:BGHCVCJVXZWKCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:349.531
Molecular Formula:C20H31NO2S
InChIKey:MMNICIJVQJJHHF-LJQANCHMSA-N
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Compound Information
Molecular Weight:176.727
Molecular Formula:C10H21Cl
InChIKey:ZTEHOZMYMCEYRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.196
Molecular Formula:C14H17Cl2NO2
InChIKey:JUKMAYKVHWKRKY-STQMWFEESA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:ORILYTVJVMAKLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:HPSNLIMZYKLBGO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.4241
Molecular Formula:C16H32O2
InChIKey:BZDBAUPOGYQGGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:354.6101
Molecular Formula:C23H46O2
InChIKey:BZNQUMHPKSWELR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.2567
Molecular Formula:C14H12N2O3
InChIKey:OXUYQWFUAOTNPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:AVVCQNALUKIMSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2
Molecular Formula:C7H6N2O2S
InChIKey:QMZUFVXOSUFZIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:547.598
Molecular Formula:C31H35BrO2Si
InChIKey:LITYHFYSBIQWNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:VVGWFVBKNAPJLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.763
Molecular Formula:C12H23ClO2
InChIKey:YBGXDWLJHNIFKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.3666
Molecular Formula:C10H22OSi
InChIKey:JJFUGCBBVOTRQK-BQYQJAHWSA-N
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Compound Information
Molecular Weight:192.683
Molecular Formula:C9H17ClO2
InChIKey:PEZGFDJJCGUPDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:FROLJCFJIQGXRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.2366
Molecular Formula:C12H14O5
InChIKey:LRYHVVHAEJMROL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.92
Molecular Formula:C6H11F6N2Sb
InChIKey:GUNLDCBYXHFZDM-UHFFFAOYSA-H
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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:110.1968
Molecular Formula:C8H14
InChIKey:IFVMAGPISVKRAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.1986
Molecular Formula:C10H10N2O2
InChIKey:WECPHHKIJBKKHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.4298
Molecular Formula:C13H26O2Si
InChIKey:KERJMUJHIKMCJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:313.23
Molecular Formula:C15H21BrO2
InChIKey:FPAUMZCNAFFSLH-CYBMUJFWSA-N
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Compound Information
Molecular Weight:238.2366
Molecular Formula:C12H14O5
InChIKey:FFDSSRAAWRBZGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.763
Molecular Formula:C12H23ClO2
InChIKey:NKMMWHWLKJHSBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.999
Molecular Formula:ClCu
InChIKey:Not Available
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Compound Information
Molecular Weight:236.2637
Molecular Formula:C13H16O4
InChIKey:VDDVOUKFJRBURC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.737
Molecular Formula:C14H17ClO2
InChIKey:YLXUMTWZCCMYGE-CYBMUJFWSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:WIXAIZPLAKQUDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.5304
Molecular Formula:C20H40O2
InChIKey:MVLVMROFTAUDAG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.192
Molecular Formula:C13H18BrNO2
InChIKey:SKBJLYFEZNRNOX-GFCCVEGCSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:JWUJQDFVADABEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:468.6126
Molecular Formula:C23H36O8Si
InChIKey:VLESTVYGLFCPPD-WSZRMNBISA-N
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Compound Information
Molecular Weight:322.0964
Molecular Formula:C10H11IO4
InChIKey:ZBIKORITPGTTGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:XFZLHJVTAFLLIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.4613
Molecular Formula:C16H26O3Si
InChIKey:GRPPDXMRSNYMPR-LSDHHAIUSA-N
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:LBDCNRRTOHEAKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.4299
Molecular Formula:C21H26O2
InChIKey:ZGPXHSXNGQKIEO-RZQBWLCQSA-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:174.2374
Molecular Formula:C9H18O3
InChIKey:YCNIYFMBSYIXJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.615
Molecular Formula:CCuF3O3S
InChIKey:YNYHGRUPNQLZHB-UHFFFAOYSA-M
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Compound Information
Molecular Weight:1563.3512
Molecular Formula:C80H84N4O16Rh2
InChIKey:RQANIUOTCDLPTP-SNLBCUCMSA-N
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Compound Information
Molecular Weight:187.2792
Molecular Formula:C10H21NO2
InChIKey:ZVWWLJKWUSJNET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:CHGRSXGBVBMMAP-AWEZNQCLSA-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:158.238
Molecular Formula:C9H18O2
InChIKey:XLBBXJVJKKWJTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:UTILDPLBMBRHQA-ZDUSSCGKSA-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:172.2646
Molecular Formula:C10H20O2
InChIKey:CVQHMHBSIYOMDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.3062
Molecular Formula:C14H19NO2
InChIKey:YAOITEVVMYJUSH-OLZOCXBDSA-N
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Compound Information
Molecular Weight:283.3648
Molecular Formula:C18H21NO2
InChIKey:JBZOHLKRXAGLNI-SJORKVTESA-N
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Compound Information
Molecular Weight:402.6422
Molecular Formula:C24H38O3Si
InChIKey:WVRLYAITLCTZFD-UHFFFAOYSA-N
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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:335.3555
Molecular Formula:C21H20O2P
InChIKey:FLYPZWDELZKIOY-UHFFFAOYSA-O
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:JAGZUIGGHGTFHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.097
Molecular Formula:C10H11BrO3
InChIKey:NEPDKGCZWSXDHF-SECBINFHSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:AEZQFUAJACYGAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.3847
Molecular Formula:C17H24N2O2
InChIKey:JWOHWTRHFIOQSH-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:172.2646
Molecular Formula:C10H20O2
InChIKey:SVZSYBFQSHHBQJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2628
Molecular Formula:C10H19NO3
InChIKey:NGIGLOKJPWGIJT-MRVPVSSYSA-N
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Compound Information
Molecular Weight:176.172
Molecular Formula:C9H8N2O2
InChIKey:HYAAEBUKCXOFDT-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:277.3157
Molecular Formula:C15H19NO4
InChIKey:CUPGWEDWMUVSGN-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:254.4943
Molecular Formula:C18H38
InChIKey:RZJRJXONCZWCBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:448.7861
Molecular Formula:C25H44O3Si2
InChIKey:KQHZKQKVJFDTEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:441.9871
Molecular Formula:C8H12O8Rh2
InChIKey:SYBXSZMNKDOUCA-UHFFFAOYSA-J
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Compound Information
Molecular Weight:254.709
Molecular Formula:C13H15ClO3
InChIKey:VBFADWUWJUDPFG-NEPJUHHUSA-N
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Compound Information
Molecular Weight:236.2637
Molecular Formula:C13H16O4
InChIKey:BLJYMLCYVOCYCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:HVGBURNSNKXAFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:LPQZERIRKRYGGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:DOXQODVJBLUBKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:RUYFBMRYAFXCLH-VOTSOKGWSA-N
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Compound Information
Molecular Weight:119.1836
Molecular Formula:C9H12
InChIKey:NCCMLVRJQAWFKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:DBSADESEDBCPFO-UHFFFAOYSA-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:120.1916
Molecular Formula:C9H12
InChIKey:JRLPEMVDPFPYPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:ZDAFYPGTJKATQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:439.6624
Molecular Formula:C26H37NO3Si
InChIKey:KRCRKLUXVQPQGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:PMTWBKPRHBNACI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:333.22
Molecular Formula:C17H17BrO2
InChIKey:DZLPYOZRSBRLET-BLLLJJGKSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:XOIVYIHYABGOTO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.3709
Molecular Formula:C14H28O2
InChIKey:MMXKVMNBHPAILY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:427.13
Molecular Formula:C17H17Br2NO2
InChIKey:QOZKLTAXTFHPNW-MRXNPFEDSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:448.35
Molecular Formula:C22H26BrNO4
InChIKey:UZEIBITWQMJULL-LJQANCHMSA-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:148.2017
Molecular Formula:C10H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:228.4033
Molecular Formula:C12H24O2Si
InChIKey:YBLZOLMWEVRCJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.3642
Molecular Formula:C18H21NO3
InChIKey:UEKQNEDOUCYVGE-SJORKVTESA-N
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Compound Information
Molecular Weight:296.3603
Molecular Formula:C19H20O3
InChIKey:RDQSMINQGDDDHO-FMEYXAORSA-N
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Compound Information
Molecular Weight:262.816
Molecular Formula:C14H27ClO2
InChIKey:WSOWFPVQNHSLBW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.5209
Molecular Formula:C19H40
InChIKey:XOJVVFBFDXDTEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.1995
Molecular Formula:C7H15NO2
InChIKey:RJSZFSOFYVMDIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:AUHZEENZYGFFBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:311.214
Molecular Formula:C15H19BrO2
InChIKey:JDHIPOFRAPLEDI-YNVXZPTESA-N
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Compound Information
Molecular Weight:173.2527
Molecular Formula:C9H19NO2
InChIKey:RKBLAXHVQYRXFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:NUGGQIWQPPASAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:355.4275
Molecular Formula:C21H25NO4
InChIKey:NKUGOLWNHFFFBI-SZGUKTLCSA-N
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Compound Information
Molecular Weight:262.816
Molecular Formula:C14H27ClO2
InChIKey:AABJXLRHKJBZSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2372
Molecular Formula:C12H14O4
InChIKey:LDMAZVHEWJAGSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.4089
Molecular Formula:C22H22O2
InChIKey:QDOOMQIGBAYDAK-XYLLXSKMSA-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:184.2753
Molecular Formula:C11H20O2
InChIKey:IOJBKMOCKWBVJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.202
Molecular Formula:C14H18BrNO2
InChIKey:RHZICMHGKFTRSN-ITDFMYJTSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:QLKUKCHPAXLOKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:WIVAMLWVBLJLNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.138
Molecular Formula:C11H14BrNO2
InChIKey:APHWYOKYHAZWMA-SNVBAGLBSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:SUFDFKRJYKNTFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1558
Molecular Formula:C6H10N2O2
InChIKey:JBVSBLLOZVDAAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:301.176
Molecular Formula:C13H17BrO3
InChIKey:VYDMDYNEDMULBU-BXKDBHETSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:IZJZWBNWUOYBQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.076
Molecular Formula:C8H10BrN
InChIKey:XYZWMVYYUIMRIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.4772
Molecular Formula:C18H36O2
InChIKey:DUWRFWKZIWPTCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.2209
Molecular Formula:C9H15NO2
InChIKey:XIOHUMRSFVEJNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:OTNDYEHGLRZQIN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1876.057
Molecular Formula:C92H124N4O16Rh2S4
InChIKey:HIKDIIUSMVGBIZ-KFIVUNIBSA-J
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:OFBQJSOFQDEBGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.617
Molecular Formula:C9H7ClN2O2
InChIKey:URTVRAIDPJOXIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3987
Molecular Formula:C13H22OSi
InChIKey:ADJGQDWJHKPZGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.5836
Molecular Formula:C22H44O2
InChIKey:YBKSMWBLSBAFBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:KXNDAVGMGPYUEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:ATIOKOODSZMQKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:NPNAIDJBODAJEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.4186
Molecular Formula:C20H26O3
InChIKey:CGNQDBPLJCEZON-PTTDNGFQSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:RQPGXPUCYFZPGQ-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:546.248
Molecular Formula:C25H22Br2O4
InChIKey:VHQFYWYQEZZOAJ-UHFFFAOYSA-N
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