Standard Article

Synthetic Uses of Tosylmethyl Isocyanide (TosMIC)

  1. Daan Van Leusen,
  2. Albert M. Van Leusen

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or057.03

Organic Reactions

Organic Reactions

How to Cite

Leusen, D. V. and Leusen, A. M. V. 2004. Synthetic Uses of Tosylmethyl Isocyanide (TosMIC). Organic Reactions. 57:3:417–666.

Author Information

  1. Groningen University, Department of Organic and Molecular Inorganic Chemistry, Groningen, The Netherlands

Publication History

  1. Published Online: 15 APR 2004

Chemistry Terms

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Abstract

TosMIC is the acronym for 4-tolylsulfonylmethyl isocyanide or tosylmethyl isocyanide. It is the best-known member of a series of about 25 sulfonyl-substituted methyl isocyanides RSO2CH2NC collected in Chart 1 (p. 426). TosMIC is a multipurpose synthetic reagent. It is by far the most versatile synthon derived from methyl isocyanide. This chapter provides a complete account of the synthetic uses of TosMIC based on a literature search closed in January 1996, and supplemented with further data available to the authors. Also included are applications of some of the more important TosMIC homologs (TosCHRNC).

TosMIC is the only commercially available sulfonylmethyl isocyanide. It is a stable, colorless, practically odorless solid, which can be stored at room temperature without decomposition.

Four brief review papers on the chemistry of TosMIC have appeared, in 1980, 1987, 1993, and 1995. Several reviews on the chemistry of isocyanides in general are available.

An effort has been made to make this chapter as complete as possible, in coverage both by tables and by references, with respect to the immediate objective: a survey of the “Synthetic Uses of TosMIC.” Emphasis is on the primary products derived from reactions of TosMIC and related isocyanides, with limited reference to the further utilization of these products. Thus, the next section gives a complete account of reductive cyanation, the conversion of aldehydes or ketones into cyanides with the use of TosMIC, but for obvious reasons synthetic applications of the product cyanides are not treated in this chapter. One of the subsequent sections describes the application of TosMIC to the synthesis of pyrroles, including 2,3-divinylpyrroles, which are important precursors in a new synthesis of indoles. This latter transformation, made possible by the easy availability of the precursors through TosMIC chemistry, is afforded brief coverage.

As a rule, reference to preliminary papers has been omitted when the same information is available from the corresponding full papers. The patent literature is covered highly selectively and is cited only when providing new and relevant information. Negative results of reactions are reported in the text or tables only when at least some relevant information is available with respect to the conditions of such unsuccessful attempts.

Keywords:

  • tosylmethyl isocyanide;
  • 4-tosylsulfonylmethyl isocyanide;
  • sulfonyl;
  • methyl isocyanide;
  • isocyanide;
  • synthetic application;
  • synthetic utility

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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:194.25
Molecular Formula:C10H10O2S
InChIKey:OPHCRBQYHONECA-YCRREMRBSA-N
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Compound Information
Molecular Weight:343.4168
Molecular Formula:C20H25NO4
InChIKey:YXWQTVWJNHKSCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:409.928
Molecular Formula:C23H20ClNO2S
InChIKey:KTYVVVZZZXSQNT-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:458.594
Molecular Formula:C23H26N2O4S2
InChIKey:IBXSTRQYFSRLHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.0826
Molecular Formula:C7H13I
InChIKey:YMPIGVKITAZKFF-ARJAWSKDSA-N
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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:157.2117
Molecular Formula:C11H11N
InChIKey:WGLKMXOTGOECNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:362.2033
Molecular Formula:C14H19IO3
InChIKey:ZDDPFEHFQRTYGW-STQMWFEESA-N
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Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-UHFFFAOYSA-N
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Molecular Weight:105.9884
Molecular Formula:CNa2O3
InChIKey:CDBYLPFSWZWCQE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:131.1729
Molecular Formula:C6H13NO2
InChIKey:CEMZBWPSKYISTN-YFKPBYRVSA-N
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Compound Information
Molecular Weight:493.701
Molecular Formula:C30H39NO3S
InChIKey:OLGGKYKCXMZAOL-ASZNTVEFSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:508.533
Molecular Formula:C23H19F3N2O4S2
InChIKey:RHMOXRGOCVXKSC-DPUYOLNOSA-N
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Compound Information
Molecular Weight:328.4452
Molecular Formula:C21H28O3
InChIKey:SUJOLEDTNRXPKI-JRSUCEMESA-N
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Compound Information
Molecular Weight:353.245
Molecular Formula:C20H14Cl2N2
InChIKey:ITCBZDBGGMJBQB-RNIAWFEPSA-N
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Compound Information
Molecular Weight:179.282
Molecular Formula:C10H13NS
InChIKey:ILAZOZMBHUDSKM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.0187
Molecular Formula:C4H9I
InChIKey:KMGBZBJJOKUPIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.157
Molecular Formula:C6H10N2
InChIKey:IYEDUTIYEAAFPU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.4711
Molecular Formula:C16H37NO
InChIKey:VDZOOKBUILJEDG-UHFFFAOYSA-M
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Compound Information
Molecular Weight:251.345
Molecular Formula:C13H17NO2S
InChIKey:UJVOYIUYZNRPPZ-UHFFFAOYSA-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:419.664
Molecular Formula:C25H41NO2S
InChIKey:DEFHSZMJHWCDSQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:329.4656
Molecular Formula:C18H23NO3Si
InChIKey:FWSNCCKSZUQABD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1778
Molecular Formula:C8H10N2O
InChIKey:LJAHNXHWRYCELC-YFHOEESVSA-N
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Compound Information
Molecular Weight:336.472
Molecular Formula:C16H20N2O2S2
InChIKey:DZMQQHGMUZXUKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:109.1689
Molecular Formula:C7H11N
InChIKey:VBWIZSYFQSOUFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:331.4076
Molecular Formula:C22H21NO2
InChIKey:USRLGZSVRPQQDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.291
Molecular Formula:C11H13NO3S
InChIKey:BLXZQORQUNDWKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:399.503
Molecular Formula:C22H25NO4S
InChIKey:SWDUIQQFQOSFQV-PIHCAMFYSA-N
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Compound Information
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:JXZJZVKLKWMWMT-GNECYAHXSA-N
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Compound Information
Molecular Weight:535.736
Molecular Formula:C29H45NO6S
InChIKey:RWNVWUOCVQBKIO-QDACKTAHSA-N
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Compound Information
Molecular Weight:100.1191
Molecular Formula:C4H8N2O
InChIKey:WJYMBVJBSFMDLE-HWKANZROSA-N
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Compound Information
Molecular Weight:190.1953
Molecular Formula:C11H10O3
InChIKey:Not Available
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Compound Information
Molecular Weight:212.2472
Molecular Formula:C13H12N2O
InChIKey:ZLSUIWYBIRBFTB-QQFPHPJOSA-N
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Compound Information
Molecular Weight:158.1998
Molecular Formula:C10H10N2
InChIKey:KSXRUTOEIGCNSN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1739
Molecular Formula:C9H10O3
InChIKey:WJUFSDZVCOTFON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.49
Molecular Formula:C12H21S3
InChIKey:PPOOLFCLQDJSPF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.4296
Molecular Formula:C18H30O2
InChIKey:PWJXHJOJJSEZAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.541
Molecular Formula:C3H7Cl
InChIKey:ULYZAYCEDJDHCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:492.61
Molecular Formula:C26H24N2O4S2
InChIKey:DOFURHLSPBIACF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:PASDCCFISLVPSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.2215
Molecular Formula:C9H15NO
InChIKey:WYUIPULDAIRYPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.0874
Molecular Formula:C4H4N2O
InChIKey:XYHKNCXZYYTLRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:455.72
Molecular Formula:C21H29NO2S4
InChIKey:WYKIPLDKRSZQIB-VXPUYCOJSA-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:275.366
Molecular Formula:C15H17NO2S
InChIKey:MVUJYJCPJLETBS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.1931
Molecular Formula:C8H12N2O2
InChIKey:HGYNMFJCKIGBJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.264
Molecular Formula:C10H11NO3S
InChIKey:KEDUXYGUIJFBON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.058
Molecular Formula:C10H5Cl2NO2
InChIKey:WLKDAZQHOLJYQE-QPJJXVBHSA-N
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Compound Information
Molecular Weight:242.315
Molecular Formula:C10H10O3S2
InChIKey:OYGMVZNPQIMDSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.251
Molecular Formula:C7H6O3S2
InChIKey:YTXGQZWWANJZPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.451
Molecular Formula:C17H25NO2S
InChIKey:JDALLCPJPAIGDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:736.684
Molecular Formula:C45H50FeN2P2
InChIKey:PPDQQFCPAFRSGS-YFRYZTMISA-N
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Compound Information
Molecular Weight:315.387
Molecular Formula:C17H17NO3S
InChIKey:BHSTZNCEDVFNKG-SJORKVTESA-N
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Compound Information
Molecular Weight:419.453
Molecular Formula:C22H17N3O4S
InChIKey:URAYNWYZGHKSKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.4029
Molecular Formula:C7H19NOSi2
InChIKey:FRCLVJBDJNNNGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:345.436
Molecular Formula:C17H15NO3S2
InChIKey:MBKGLXSZFYEGEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.345
Molecular Formula:C13H17NO2S
InChIKey:QFMMNNLZAPGDGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:255.333
Molecular Formula:C12H17NO3S
InChIKey:UMWJDBQVMGZUES-BXKDBHETSA-N
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Compound Information
Molecular Weight:240.4677
Molecular Formula:C17H36
InChIKey:NDJKXXJCMXVBJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:541.613
Molecular Formula:C28H31NO8S
InChIKey:ACRCDLXYWZFQER-WGOQTCKBSA-N
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Compound Information
Molecular Weight:120.17
Molecular Formula:C4H8O2S
InChIKey:HXJUTPCZVOIRIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:PCAOATPQPDNETE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:IZALUMVGBVKPJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:358.412
Molecular Formula:C18H18N2O4S
InChIKey:FNXSUGWPFCEMBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:434.464
Molecular Formula:C23H18N2O5S
InChIKey:AWCVJJCCROTZBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.345
Molecular Formula:C16H13NO2S
InChIKey:UNZVFMPQSIKNRU-FOWTUZBSSA-N
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Compound Information
Molecular Weight:281.446
Molecular Formula:C13H19NO2SSi
InChIKey:QDCWUEDMOFOAEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.322
Molecular Formula:C14H12N2O2S
InChIKey:BZKWJXSPTMRDGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.435
Molecular Formula:C17H23NO2S
InChIKey:OWBJYLSAISZSOH-SREVYHEPSA-N
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Compound Information
Molecular Weight:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight: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:174.1199
Molecular Formula:C8H5F3O
InChIKey:Not Available
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:KPMKEVXVVHNIEY-RITPCOANSA-N
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Compound Information
Molecular Weight:167.271
Molecular Formula:C9H13NS
InChIKey:BJANPDOQTUMTHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.2007
Molecular Formula:C7H15N
InChIKey:HTLZVHNRZJPSMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:421.469
Molecular Formula:C22H19N3O4S
InChIKey:CTTFSZWKXNLOSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:382.519
Molecular Formula:C22H26N2O2S
InChIKey:RVMJNECWSAFPIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:397.489
Molecular Formula:C25H19NO2S
InChIKey:GHHDWHRYWMMXBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.055
Molecular Formula:C4H9LiO
InChIKey:LZWQNOHZMQIFBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.773
Molecular Formula:C13H22ClN
InChIKey:HTZCNXWZYVXIMZ-UHFFFAOYSA-M
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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:227.28
Molecular Formula:C10H13NO3S
InChIKey:AHJDPUKHBRUPBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.254
Molecular Formula:C9H11NO3S
InChIKey:XEHIIYMZJQMMCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2393
Molecular Formula:C15H10O
InChIKey:QCQPEPJFSJXQSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.467
Molecular Formula:C20H23NO2S
InChIKey:QHRDQZJETBWIFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:455.72
Molecular Formula:C21H29NO2S4
InChIKey:ALDPUVQZDLZPFH-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:404.525
Molecular Formula:C24H24N2O2S
InChIKey:BTOPRCGTOKVFQT-YZSQISJMSA-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:235.302
Molecular Formula:C12H13NO2S
InChIKey:PWESCSWWUKIFSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.275
Molecular Formula:C8H15NO3S
InChIKey:HGYXNFMABAMDGW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:271.334
Molecular Formula:C15H13NO2S
InChIKey:KIJCBVOPJSHLBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:273.31
Molecular Formula:C13H11N3O2S
InChIKey:QPSBULOAZPKQHX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:429.4263
Molecular Formula:C27H15N3O3
InChIKey:VNEZNXOXGQBRTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.018
Molecular Formula:C4H9Br
InChIKey:UPSXAPQYNGXVBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:326.4293
Molecular Formula:C21H26O3
InChIKey:YWRQUKQBUQAGFV-WIRSXHRWSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:391.483
Molecular Formula:C23H21NO3S
InChIKey:RJQKCXIUKYJTTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.056
Molecular Formula:C6H11I
InChIKey:FUCOMWZKWIEKRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.437
Molecular Formula:C3H6BrCl
InChIKey:MFESCIUQSIBMSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2111
Molecular Formula:C11H11NO
InChIKey:WKMCWOTXEGTBFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:624.726
Molecular Formula:C34H28N2O6S2
InChIKey:XBZIPNHXGPWLTN-LBYUQGKWSA-N
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Compound Information
Molecular Weight:335.419
Molecular Formula:C20H17NO2S
InChIKey:SIXJNDYLCCMEAN-PJQLUOCWSA-N
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Compound Information
Molecular Weight:96.0874
Molecular Formula:C4H4N2O
InChIKey:GAJBWMUZVXJIBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:MSHDDUOBOGDHLQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:510.087
Molecular Formula:C29H32ClNO3S
InChIKey:VBFSYSGIVAHFFT-AXZKNTKESA-N
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Compound Information
Molecular Weight:329.374
Molecular Formula:C16H15N3O3S
InChIKey:XNYKIVFUNJOMSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.194
Molecular Formula:C7H8O2S
InChIKey:FXJVNINSOKCNJP-UHFFFAOYSA-M
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Compound Information
Molecular Weight:325.446
Molecular Formula:C15H19NO3S2
InChIKey:QGIQYXYIKUGHSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:343.397
Molecular Formula:C18H17NO4S
InChIKey:QCZNPCBCPADULW-LDADJPATSA-N
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Compound Information
Molecular Weight:1066.9
Molecular Formula:C64H44Cl4N8
InChIKey:AQFXEVLBZVEBHC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:534.69
Molecular Formula:C29H30N2O4S2
InChIKey:FQZLWBUEFHZIPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.203
Molecular Formula:C7H8S
InChIKey:WLHCBQAPPJAULW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.888
Molecular Formula:C3H6Br2
InChIKey:VEFLKXRACNJHOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:395.556
Molecular Formula:C21H33NO4S
InChIKey:BOCFHGAQZWWQES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.323
Molecular Formula:C17H17NO
InChIKey:KOGXIYUGGLIUDJ-VAWYXSNFSA-N
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Compound Information
Molecular Weight:320.385
Molecular Formula:C20H20N2O2
InChIKey:AOIVSPXHXZYLIQ-HPIZBCMHSA-N
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Compound Information
Molecular Weight:71.121
Molecular Formula:C4H9N
InChIKey:AZDJPUNWDYYMIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2001
Molecular Formula:C7H16O3
InChIKey:GKASDNZWUGIAMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.4186
Molecular Formula:C20H25NO
InChIKey:PMLVHVJQCYCXRO-ZAUVMOETSA-N
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Compound Information
Molecular Weight:270.346
Molecular Formula:C16H14O2S
InChIKey:YEZOZPNTUYZRAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:AWJUIBRHMBBTKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:443.4
Molecular Formula:C8H12O8Pb
InChIKey:Not Available
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Compound Information
Molecular Weight:168.1946
Molecular Formula:C11H8N2
InChIKey:BMMCNKYHQAKJBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:31.0571
Molecular Formula:CH5N
InChIKey:BAVYZALUXZFZLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2963
Molecular Formula:C10H23N
InChIKey:OZIXTIPURXIEMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:CMOKFBMAFUYELN-PLNGDYQASA-N
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Compound Information
Molecular Weight:187.861
Molecular Formula:C2H4Br2
InChIKey:PAAZPARNPHGIKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.3374
Molecular Formula:C20H14N2O2
InChIKey:SJFDJRRRAZSUAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2423
Molecular Formula:C11H16O4
InChIKey:WTQDGOCRQVFUFA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:XMLSXPIVAXONDL-PLNGDYQASA-N
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Compound Information
Molecular Weight:273.352
Molecular Formula:C12H16LiNO2SSi
InChIKey:SJYIOHSJBVZASX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.725
Molecular Formula:C10H12ClNO3S
InChIKey:JVULQPACIXFOBU-ZRDIBKRKSA-N
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Compound Information
Molecular Weight:521.625
Molecular Formula:C29H31NO6S
InChIKey:MWBMZNODUGZSAT-TZADPSAESA-N
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Compound Information
Molecular Weight:226.2307
Molecular Formula:C13H10N2O2
InChIKey:NYJOAZXGKLCRSV-GXDHUFHOSA-N
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Compound Information
Molecular Weight:185.565
Molecular Formula:C7H4ClNO3
InChIKey:SKDHHIUENRGTHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.382
Molecular Formula:C15H19NO2S
InChIKey:CCIRUWKJEJFBAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.397
Molecular Formula:C15H21NO3S
InChIKey:WAEDAWLDYUWTKS-WYMLVPIESA-N
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Compound Information
Molecular Weight:219.2829
Molecular Formula:C12H17N3O
InChIKey:NEIQXBBHPZTENX-RIYZIHGNSA-N
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Compound Information
Molecular Weight:309.382
Molecular Formula:C18H15NO2S
InChIKey:SIJZCWAJHPPMPR-CVCOPPNTSA-N
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Compound Information
Molecular Weight:81.076
Molecular Formula:C3H3N3
InChIKey:JIHQDMXYYFUGFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2173
Molecular Formula:C13H10O2
InChIKey:BVAGSGSYUAOFPJ-CMDGGOBGSA-N
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.307
Molecular Formula:C11H15NO3S
InChIKey:VEVBNKUSKZDZOI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.097
Molecular Formula:C10H11BrO2
InChIKey:RDEWTAHSEKSPPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:QHUHMAOJQQHMFO-BQBZGAKWSA-N
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Compound Information
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:ZSKGQVFRTSEPJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:407.525
Molecular Formula:C24H25NO3S
InChIKey:ZBTXOSOPUMZZML-SAPNQHFASA-N
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Compound Information
Molecular Weight:135.1433
Molecular Formula:C7H7N2O
InChIKey:NDBJTKNWAOXLHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:381.488
Molecular Formula:C22H23NO3S
InChIKey:UEPSDGOFQWJCIH-PWRODBHTSA-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:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.109
Molecular Formula:C8H20O4Ti
InChIKey:JMXKSZRRTHPKDL-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:492.61
Molecular Formula:C26H24N2O4S2
InChIKey:FZVLOEBDVGWYSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.312
Molecular Formula:C13H13NO4S
InChIKey:YHCVJRMTGGFZLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.1613
Molecular Formula:C8H8N2O2
InChIKey:NTWGFNWYTUGVSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:479.457
Molecular Formula:C21H21NO10S
InChIKey:YMUJYGFWJQVLMN-GDNBJRDFSA-N
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Compound Information
Molecular Weight:325.446
Molecular Formula:C15H19NO3S2
InChIKey:CFSMKEXSYXLGKJ-CCEZHUSRSA-N
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Compound Information
Molecular Weight:275.366
Molecular Formula:C15H17NO2S
InChIKey:MVUJYJCPJLETBS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.276
Molecular Formula:C11H11NO2S
InChIKey:BOMIJCVZAIXUQB-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:159.1879
Molecular Formula:C9H9N3
InChIKey:WVFGUPZLWPFVIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.083
Molecular Formula:C6H6Cl2S
InChIKey:OJBWNBCXVFAMEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HGKVDALQZGEOJH-QHHAFSJGSA-N
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Compound Information
Molecular Weight:289.393
Molecular Formula:C16H19NO2S
InChIKey:DLZMGBDJSVDRKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:624.812
Molecular Formula:C36H36N2O4S2
InChIKey:OARAUVRWDXXWDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:361.412
Molecular Formula:C18H19NO5S
InChIKey:CFVADIWZINGOFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:367.4813
Molecular Formula:C23H29NO3
InChIKey:NLUVLMOZCPDZEH-WRRMCANASA-N
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Compound Information
Molecular Weight:209.265
Molecular Formula:C10H11NO2S
InChIKey:OMFGTLYTNSXPGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:255.742
Molecular Formula:C16H14ClN
InChIKey:WKBKSKHGVIKYKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:YPYPBEGIASEWKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.1846
Molecular Formula:C10H9NO
InChIKey:AZNMFVGFAFVVDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2077
Molecular Formula:C8H12N4
InChIKey:OZAIFHULBGXAKX-VAWYXSNFSA-N
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Compound Information
Molecular Weight:270.71
Molecular Formula:C16H11ClO2
InChIKey:FDRLLMAFDMQAJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.2744
Molecular Formula:C14H15NO2
InChIKey:DOMGTGLLHCBOLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.004
Molecular Formula:C8Cl2N2O2
InChIKey:HZNVUJQVZSTENZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.382
Molecular Formula:C15H19NO2S
InChIKey:WRPIHSUVUGFELS-WAYWQWQTSA-N
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Compound Information
Molecular Weight:149.89424
Molecular Formula:INa
InChIKey:FVAUCKIRQBBSSJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:305.372
Molecular Formula:C14H11NO3S2
InChIKey:NWANKYAFORYFFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2548
Molecular Formula:C10H17N2O
InChIKey:KVTOSAMSZMXLKB-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:214.3061
Molecular Formula:C14H18N2
InChIKey:PPXHSCDLAZGQKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:CQPDOPCUMQSGHZ-DTQAZKPQSA-N
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Compound Information
Molecular Weight:486.5556
Molecular Formula:C30H30O6
InChIKey:DWJHQBCZHPQUNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.3746
Molecular Formula:C6H18NNaSi2
InChIKey:WRIKHQLVHPKCJU-UHFFFAOYSA-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:152.2334
Molecular Formula:C10H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:507.684
Molecular Formula:C30H37NO4S
InChIKey:KSJLZJSLFCTEEZ-DDDCQWJZSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:GJUJYHIUGGUILF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:412.4786
Molecular Formula:C30H20O2
InChIKey:UANJKTXYCCFKIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:600.771
Molecular Formula:C32H28N2O4S3
InChIKey:MZEHALIXIPWSHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:285.361
Molecular Formula:C16H15NO2S
InChIKey:XBGXGWNKJBMMPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:451.413
Molecular Formula:C20H17CrNO6S
InChIKey:WXKCFWLVPKIFAJ-NHJIBSTCSA-N
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Compound Information
Molecular Weight:211.2576
Molecular Formula:C11H17NO3
InChIKey:QSUCQAULQIAOEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.177
Molecular Formula:C6H6S
InChIKey:RMVRSNDYEFQCLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:338.037
Molecular Formula:C14H10Br2
InChIKey:GOQAUHRRVINDLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:HMGXRGDTHQEUAO-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:631.78
Molecular Formula:C32H45N3O8S
InChIKey:VXROAFQKOKZATI-HSJPWVCISA-N
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Compound Information
Molecular Weight:255.333
Molecular Formula:C12H17NO3S
InChIKey:KEXWUIJTHJBCLT-BEYAYEFLSA-N
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Compound Information
Molecular Weight:368.289
Molecular Formula:C16H18BrNO2S
InChIKey:JEFFZKCATIQAPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:293.983
Molecular Formula:C9H10Br2O
InChIKey:RIUVOPXHNGAESY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.339
Molecular Formula:C14H15NO2S
InChIKey:YVOQWUVPSMDFFC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:521.651
Molecular Formula:C27H27N3O4S2
InChIKey:OKLBSCLPAVWONB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.184
Molecular Formula:C10H9NO2
InChIKey:HXAORLISYKTFNQ-KBXRYBNXSA-N
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Compound Information
Molecular Weight:380.46
Molecular Formula:C21H20N2O3S
InChIKey:FVMZSCTVVUVGIV-YHRLJZSWSA-N
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Compound Information
Molecular Weight:265.2667
Molecular Formula:C15H11N3O2
InChIKey:GWXYONHRNZUHBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:289.35
Molecular Formula:C15H15NO3S
InChIKey:CLISTJAYEKDBHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.302
Molecular Formula:C12H13NO2S
InChIKey:OEZHRMOVCQGFOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.5949
Molecular Formula:C23H44O
InChIKey:POUPCVYXSMXVRS-SEYXRHQNSA-N
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Compound Information
Molecular Weight:317.36
Molecular Formula:C16H15NO4S
InChIKey:IUAICUMHEWZZQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.2421
Molecular Formula:C13H25I
InChIKey:INZRRRZJJUOCER-KTKRTIGZSA-N
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Compound Information
Molecular Weight:266.2946
Molecular Formula:C16H14N2O2
InChIKey:JOUANZJWIPNHPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:493.658
Molecular Formula:C29H35NO4S
InChIKey:XEAMLIGEYIEMKB-BAXDJTGNSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-QPJJXVBHSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:303.376
Molecular Formula:C16H17NO3S
InChIKey:CMAKZBGAAUGQMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.238
Molecular Formula:C9H17N
InChIKey:BTABJYHCXAIQAO-UXBLZVDNSA-N
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Compound Information
Molecular Weight:294.3875
Molecular Formula:C20H22O2
InChIKey:RWECEVUBBRUMDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:AHOKGTBIWXGZNE-GARJFASQSA-N
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Compound Information
Molecular Weight:299.348
Molecular Formula:C15H13N3O2S
InChIKey:HDSPZYQTPAUMDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:319.375
Molecular Formula:C16H17NO4S
InChIKey:YOCNSPQUZQVTKG-MDZDMXLPSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:PJGSXYOJTGTZAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.344
Molecular Formula:C16H13NO3S
InChIKey:ZTHSOVHOPOYFNZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.234
Molecular Formula:C7H11NS
InChIKey:Not Available
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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:282.4614
Molecular Formula:C18H34O2
InChIKey:ZQPPMHVWECSIRJ-KTKRTIGZSA-N
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Compound Information
Molecular Weight:375.462
Molecular Formula:C18H17NO4S2
InChIKey:PNKOIATUZFKVEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.265
Molecular Formula:C10H11NO2S
InChIKey:NGOUPILQFWOEET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:BBHOMWITKYDNSJ-ONEGZZNKSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:KCVSCETUCBKXJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.36
Molecular Formula:C16H14N2O2S
InChIKey:KQVTWUODLBTLCN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:61.04
Molecular Formula:CH3NO2
InChIKey:LYGJENNIWJXYER-UHFFFAOYSA-N
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