Standard Article

Palladium-Catalyzed Vinylation of Organic Halides

  1. Richard F. Heck

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or027.02

Organic Reactions

Organic Reactions

How to Cite

Heck, R. F. 2005. Palladium-Catalyzed Vinylation of Organic Halides. Organic Reactions. 27:2:345–390.

Author Information

  1. University of Delaware, Newark, Delaware

Publication History

  1. Published Online: 15 JUL 2005

Chemistry Terms

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Abstract

The palladium-catalyzed vinylation of organic halides provides a very convenient method for forming carbon[BOND]carbon bonds at unsubstituted vinylic positions. Generally the reaction does not require anhydrous or anaerobic conditions although it is advisable to limit access of oxygen when arylphosphines are used as a component of the catalyst. The transformation is valuable because it cannot be carried out in a single step by any other known method (except in certain Meerwein reactions).

The organic halide employed is limited to aryl, heterocyclic, benzyl, or vinyl types, with bromides and iodides seen most often. Halides with an easily eliminated beta-hydrogen atom (i.e., alkyl derivatives) cannot be used since they form only olefins by elimination under the normal reaction conditions. The base needed may be a secondary or tertiary amine, sodium or potassium acetate, carbonate, or bicarbonate.

When nucleophilic secondary amines are used as coreactants with most vinylic halides, a variation occurs that often produces tertiary allylic amines as major products. The catalyst is commonly palladium acetate, although palladium chloride or preformed triarylphosphine palladium complexes, as well as palladium on charcoal, have been used. A reactant, product, or solvent may serve as the ligand in reactions involving organic iodides, but generally a triarylphosphine or a secondary amine is required when organic bromides are used. The reaction, which occurs between ca. 50° and 160° proceeds homogeneously. Solvents such as acetonitrile, dimethylformamide, hexamethylphosphoramide, N-methylpyrrolidinone, and methanol have been used, but are often not necessary. The procedure is applicable to a very wide range of reactants and yields are generally good to excellent.

Several variations of the reaction are known in which the organic halide is replaced by other reagents such as organometallics, diazonium salts, or aromatic hydrocarbons. These reactions are not discussed in detail, but are only briefly compared with the halide reaction. Other related reactions such as the palladium-catalyzed replacement of allylic substituents with carbanionic reagents, the palladium-promoted nucleophilic substitutions at olefinic carbons, and the numerous palladium-catalyzed coupling reactions of halides and organometallics are also beyond the scope of this review. The palladium-catalyzed vinylic substitution reaction has not yet received much attention from organic chemists, but its broad scope and simplicity demonstrate that it is a useful method for the synthesis of a variety of olefinic compounds.

Keywords:

  • palladium catalyst;
  • vinylation;
  • organic halides;
  • scope;
  • limitations;
  • experimental procedures;
  • vinylic substitution;
  • ethylene;
  • acrylic acid;
  • butenol;
  • methyl acrylate;
  • styrene;
  • pentadiene;
  • acrolein dimethyl acetal;
  • olefins

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
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:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:212.2423
Molecular Formula:C11H16O4
InChIKey:PYOTTWNQFUIUJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.055
Molecular Formula:C9H6BrN
InChIKey:ZGIKWINFUGEQEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:VHVMXWZXFBOANQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.002
Molecular Formula:C4H7Br
InChIKey:UILZQFGKPHAAOU-ARJAWSKDSA-N
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Compound Information
Molecular Weight:229.3605
Molecular Formula:C16H23N
InChIKey:VPGFLQGHSMDMJI-CMDGGOBGSA-N
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Compound Information
Molecular Weight:268.2641
Molecular Formula:C16H12O4
InChIKey:ATCSGDJWJHCRLV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:209.3278
Molecular Formula:C13H23NO
InChIKey:APCDIKGORNLOPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1732
Molecular Formula:C9H8N2
InChIKey:BYEHYSHPUIZTSR-HWKANZROSA-N
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Compound Information
Molecular Weight:243.2579
Molecular Formula:C14H13NO3
InChIKey:SFTVKJOXXYGQSA-BQYQJAHWSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:RZIOPNWLBZGHAN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:PZAXWHVVPMHDMR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MBYZVRLALPKNQV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.3171
Molecular Formula:C12H23NO
InChIKey:ZLYGKWFKDWRROX-VOTSOKGWSA-N
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Compound Information
Molecular Weight:219.2365
Molecular Formula:C12H13NO3
InChIKey:NVPUAPCWSYBSQR-VMPITWQZSA-N
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Compound Information
Molecular Weight:105.9884
Molecular Formula:CNa2O3
InChIKey:CDBYLPFSWZWCQE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:212.265
Molecular Formula:C10H12O3S
InChIKey:ZYVGYMLIYDLKHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.002
Molecular Formula:C4H7Br
InChIKey:DEFNUDNHTUZJAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:HNVRRHSXBLFLIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.114
Molecular Formula:C10H13Br
InChIKey:XHCAGOVGSDHHNP-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:162.2283
Molecular Formula:C11H14O
InChIKey:KECGKFACUFUPMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:WBYWAXJHAXSJNI-VOTSOKGWSA-N
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Compound Information
Molecular Weight:157.008
Molecular Formula:C6H5Br
InChIKey:QARVLSVVCXYDNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3026
Molecular Formula:C18H14O2
InChIKey:VYQBJNASNJHPFC-ZHACJKMWSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:VWXZFDWVWMQRQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.42
Molecular Formula:Pd
InChIKey:KDLHZDBZIXYQEI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.3278
Molecular Formula:C13H23NO
InChIKey:NIGFJOCXRMWYOG-HITCCNIDSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:NITWSHWHQAQBAW-QPJJXVBHSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:NZLCAHVLJPDRBL-VSAQMIDASA-N
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Compound Information
Molecular Weight:213.051
Molecular Formula:C8H8BrNO
InChIKey:MSLICLMCQYQNPK-UHFFFAOYSA-M
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:42.0797
Molecular Formula:C3H6
InChIKey:QQONPFPTGQHPMA-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:LIKMAJRDDDTEIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.0627
Molecular Formula:C3H4O2
InChIKey:NIXOWILDQLNWCW-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:148.2017
Molecular Formula:C10H12O
InChIKey:MYHGOWDLVRDUFA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.1953
Molecular Formula:C11H10O3
InChIKey:KVXMLLMZXPRPNG-VOTSOKGWSA-N
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Compound Information
Molecular Weight:236.2653
Molecular Formula:C16H12O2
InChIKey:NCAJMNHLAZAVRZ-OWOJBTEDSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:OHLUUHNLEMFGTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:WRCBAWDQQSQNRE-FNORWQNLSA-N
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Compound Information
Molecular Weight:205.2099
Molecular Formula:C11H11NO3
InChIKey:ANVZQEASRUZEQM-VOTSOKGWSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:SJNALLRHIVGIBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.3165
Molecular Formula:C12H23NO2
InChIKey:WGYMHPUTLFMAMT-QPJJXVBHSA-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:294.3477
Molecular Formula:C18H18N2O2
InChIKey:UVPMLXBZUJILHQ-ONEGZZNKSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:WNOJZYDKNANUOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.203
Molecular Formula:C7H8OS
InChIKey:QDTQNHLHBKGUBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:GNQAZNILNLQRJV-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:87.1204
Molecular Formula:C4H9NO
InChIKey:YNAVUWVOSKDBBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:JTUYEZAVXJDUOM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.079
Molecular Formula:C13H12FeO
InChIKey:LGDKSORFZZMCBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:OBWGMYALGNDUNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.1806
Molecular Formula:C11H9F5O
InChIKey:FRVAIUGOSDOGIG-VOTSOKGWSA-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:225.006
Molecular Formula:C7H4BrF3
InChIKey:XLQSXGGDTHANLN-UHFFFAOYSA-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:138.2499
Molecular Formula:C10H18
InChIKey:DTIGTFJLLYWKTF-BQYQJAHWSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:CGNYOQPDQQGWMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2753
Molecular Formula:C11H19N
InChIKey:LXHOLLGOHQJSTH-UXBLZVDNSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:NBYHMFDDBVFUBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2111
Molecular Formula:C11H11NO
InChIKey:IDVUZHTZUDEXPU-KBXRYBNXSA-N
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Compound Information
Molecular Weight:207.1828
Molecular Formula:C10H9NO4
InChIKey:VKKNUVQQEHKTCG-VOTSOKGWSA-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:190.2814
Molecular Formula:C13H18O
InChIKey:XJRSLESCJFYMRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:701.9
Molecular Formula:C36H30Cl2P2Pd
InChIKey:YNHIGQDRGKUECZ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:WYHCWIYFRRDJDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:DGMYRPFYNFQCHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.949
Molecular Formula:C2H3Br
InChIKey:INLLPKCGLOXCIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:437.824
Molecular Formula:C10H8FeI2
InChIKey:INPBOTSWXSPAQM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2717
Molecular Formula:C15H14
InChIKey:OVZXISBUYCEVEV-SEYXRHQNSA-N
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Compound Information
Molecular Weight:226.292
Molecular Formula:C11H14O3S
InChIKey:KTLWBWDYVKBSKC-HWKANZROSA-N
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Compound Information
Molecular Weight:282.904
Molecular Formula:C6H4BrI
InChIKey:OIRHKGBNGGSCGS-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:126.583
Molecular Formula:C7H7Cl
InChIKey:KCXMKQUNVWSEMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:ZCHVBOFKMHFJSQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:FJKIXWOMBXYWOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.036
Molecular Formula:C4H3BrS
InChIKey:TUCRZHGAIRVWTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:NRMSDBSOGLOCJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.0078
Molecular Formula:C6H5IO
InChIKey:VSMDINRNYYEDRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:QGFMYBPEBFTCIN-AATRIKPKSA-N
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Compound Information
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:HGXLQVRIACSGIQ-KQQUZDAGSA-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:235.098
Molecular Formula:C7H7BrO2S
InChIKey:KEYPHZZYKZVXLU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2982
Molecular Formula:C16H16
InChIKey:ARZIVALJTPLLHF-VAWYXSNFSA-N
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Compound Information
Molecular Weight:199.088
Molecular Formula:C9H11Br
InChIKey:MOZHUOIQYVYEPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:ZFNVDHOSLNRHNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:402.3961
Molecular Formula:C24H18O6
InChIKey:ADBZVGRSXZPXDQ-FYWRMAATSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.0846
Molecular Formula:C5H5F5O
InChIKey:BODBNAUGXOXYEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:269.4228
Molecular Formula:C16H31NO2
InChIKey:FWJQLJUOADUGMN-PKNBQFBNSA-N
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Compound Information
Molecular Weight:326.211
Molecular Formula:C18H22FeO2
InChIKey:FCKVPPQAFYGXKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.1846
Molecular Formula:C10H10O3
InChIKey:YMXREWKKROWOSO-VOTSOKGWSA-N
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Compound Information
Molecular Weight:185.018
Molecular Formula:C7H5BrO
InChIKey:Not Available
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Compound Information
Molecular Weight:157.996
Molecular Formula:C5H4BrN
InChIKey:NYPYPOZNGOXYSU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:QBFNGLBSVFKILI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:RORKCJRKDMOOIQ-YDFGWWAZSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:SIIPGKCVJBONMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.2319
Molecular Formula:C13H11NO2
InChIKey:PUGNCMWPWJFYCX-VOTSOKGWSA-N
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Compound Information
Molecular Weight:229.071
Molecular Formula:C9H9BrO2
InChIKey:XZIAFENWXIQIKR-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:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-KXFIGUGUSA-N
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Compound Information
Molecular Weight:215.044
Molecular Formula:C8H7BrO2
InChIKey:SWGQITQOBPXVRC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:OXAOLOBMDYZLOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2212
Molecular Formula:C12H11NO2
InChIKey:VGUYJFPHWVNEQV-HWKANZROSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:BATOPAZDIZEVQF-AWYLAFAOSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:WSNAMTOWWQGIQS-SOFGYWHQSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:SJYDWTUGCAEBTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:NJGBTKGETPDVIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:MWQHKOLUSZNRIU-NEVGTANLSA-N
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Compound Information
Molecular Weight:241.081
Molecular Formula:C10H9BrO2
InChIKey:MFKOGXVHZUSUAF-QPJJXVBHSA-N
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Compound Information
Molecular Weight:125.2114
Molecular Formula:C8H15N
InChIKey:KYGMSGYKSGNPHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.3431
Molecular Formula:C13H25NO2
InChIKey:KTSKAAWZIUELTH-KPKJPENVSA-N
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Compound Information
Molecular Weight:196.044
Molecular Formula:C8H6BrN
InChIKey:VXWVFZFZYXOBTA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:392.052
Molecular Formula:C22H16Fe2
InChIKey:RUYCARACVNLTJD-GWIKJDHCSA-N
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Compound Information
Molecular Weight:233.104
Molecular Formula:C12H9Br
InChIKey:KTADSLDAUJLZGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:FMFHUEMLVAIBFI-BQYQJAHWSA-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:70.1329
Molecular Formula:C5H10
InChIKey:Not Available
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Compound Information
Molecular Weight:215.044
Molecular Formula:C8H7BrO2
InChIKey:CZNGTXVOZOWWKM-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:73.1368
Molecular Formula:C4H11N
InChIKey:HPNMFZURTQLUMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:AWRZGEGJIHZJET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:UKEXEDXJYSMZGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.167
Molecular Formula:C12H17Br
InChIKey:KSFMKBVDTMONEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.202
Molecular Formula:C7H8O2S
InChIKey:KNKIXYMOHMYZJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:237.381
Molecular Formula:C15H27NO
InChIKey:SUOJGZQRVLBEAU-RRHGIDMASA-N
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:NVZWEEGUWXZOKI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.056
Molecular Formula:C6H11I
InChIKey:CDQXWFGHOVDYNN-AATRIKPKSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:BCRJHHFLBOQAMG-YNRRLODASA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:AKGGYBADQZYZPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.081
Molecular Formula:C10H8BrNO
InChIKey:AYFPZXVRXRMCQX-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:227.3431
Molecular Formula:C13H25NO2
InChIKey:FXZJOXKONRSQDO-BQYQJAHWSA-N
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Compound Information
Molecular Weight:261.3593
Molecular Formula:C16H23NO2
InChIKey:RIFBMSZEEFQGJR-CPSFFCFKSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:UTPOSGXXIJEVFD-AATRIKPKSA-N
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Compound Information
Molecular Weight:406.079
Molecular Formula:C23H18Fe2
InChIKey:CCMIIIGOFNWOIA-RKKUYNIKSA-N
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Compound Information
Molecular Weight:260.1147
Molecular Formula:C10H13I
InChIKey:WQVIVQDHNKQWTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:IQIJIAHSHBJYCO-VMPITWQZSA-N
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Compound Information
Molecular Weight:171.034
Molecular Formula:C7H7Br
InChIKey:ZBTMRBYMKUEVEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:KAKZBPTYRLMSJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.036
Molecular Formula:C4H3BrS
InChIKey:XCMISAPCWHTVNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:PQZQCZMROHXKBX-XBLVEGMJSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:GRHVNFMUNHLGAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.072
Molecular Formula:C6H5BrOS
InChIKey:IGBZCOWXSCWSHO-UHFFFAOYSA-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:208.055
Molecular Formula:C9H6BrN
InChIKey:SCRBSGZBTHKAHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:CPJRRXSHAYUTGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:VNRMUGSMIGLPOH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.976
Molecular Formula:C3H5Br
InChIKey:NNQDMQVWOWCVEM-IHWYPQMZSA-N
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:VEZIKIAGFYZTCI-VMPITWQZSA-N
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Compound Information
Molecular Weight:220.2213
Molecular Formula:C12H12O4
InChIKey:OHHRWWCYKPUJOW-VMPITWQZSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:ULNCTPWTLOVYFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2078
Molecular Formula:C12H10
InChIKey:ZUOUZKKEUPVFJK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:521.9874
Molecular Formula:C36H75N
InChIKey:SWZDQOUHBYYPJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.007
Molecular Formula:C6H5BrO
InChIKey:GZFGOTFRPZRKDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.3593
Molecular Formula:C16H23NO2
InChIKey:NQZHFMKANAIMNQ-ONEGZZNKSA-N
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Compound Information
Molecular Weight:169.264
Molecular Formula:C10H19NO
InChIKey:LMSZURFLDHMISN-ONNFQVAWSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:VOEDRUGFNJEWGQ-VMPITWQZSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:BUIRDOGDCJQFDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2225
Molecular Formula:C12H12O2
InChIKey:OXWQBUHCJNXFLV-NXZHAISVSA-N
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Compound Information
Molecular Weight:162.1852
Molecular Formula:C10H10O2
InChIKey:PEXWJYDPDXUVSV-BQYQJAHWSA-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:514.7639
Molecular Formula:C36H51P
InChIKey:MEYTUZLAONGIPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:PBKGDGNXERIGPN-WEVVVXLNSA-N
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Compound Information
Molecular Weight:140.203
Molecular Formula:C7H8OS
InChIKey:LWLHFHDNURUMPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YGCZTXZTJXYWCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.056
Molecular Formula:C6H11I
InChIKey:TUAPXMNNQGXDDV-WAYWQWQTSA-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:190.1953
Molecular Formula:C11H10O3
InChIKey:FECOKXYSVFVXRX-VOTSOKGWSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:COUZAGXGXFTWTH-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:72.1057
Molecular Formula:C4H8O
InChIKey:WCASXYBKJHWFMY-IHWYPQMZSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:NSHDCQDEOQUPLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:FINOPSACFXSAKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:WHVMBCYJSIPUIU-GORDUTHDSA-N
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Compound Information
Molecular Weight:207.067
Molecular Formula:C10H7Br
InChIKey:DLKQHBOKULLWDQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:MYRTYDVEIRVNKP-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:110.1968
Molecular Formula:C8H14
InChIKey:QTYUSOHYEPOHLV-FNORWQNLSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:YHDAVYIJOHPWFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:IBHTVMUPFNHFLY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.0078
Molecular Formula:C6H5IO
InChIKey:FXTKWBZFNQHAAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:AHPWAHONMBZZRZ-YTXTXJHMSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:MNGYPDQJVYJTLM-MDZDMXLPSA-N
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Compound Information
Molecular Weight:149.1467
Molecular Formula:C8H7NO2
InChIKey:VKVLTUQLNXVANB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.3975
Molecular Formula:C15H29N
InChIKey:SAFDOXBKBWXZBG-FMIVXFBMSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:SECXISVLQFMRJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:VVQNEPGJFQJSBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:472.6842
Molecular Formula:C33H45P
InChIKey:BYVSUDNLPOHACR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:SXJFCAFFGQCNLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.1996
Molecular Formula:C11H11F3O
InChIKey:MZBMFWOOKDHWEH-NSCUHMNNSA-N
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Compound Information
Molecular Weight:318.495
Molecular Formula:C24H30
InChIKey:MVZVDAGWAAZJPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:166.263
Molecular Formula:C8H6S2
InChIKey:IAAQEGBHNXAHBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:KPSGIKJCDXCBGR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:BOPPSUHPZARXTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:MQGVOSGGRHAKOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:28.0532
Molecular Formula:C2H4
InChIKey:Not Available
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:PAYRUJLWNCNPSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.1828
Molecular Formula:C10H9NO4
InChIKey:NVXKMHUNXMXXDM-QPJJXVBHSA-N
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Compound Information
Molecular Weight:149.029
Molecular Formula:C5H9Br
InChIKey:QWXOKLBTBADFAI-SNAWJCMRSA-N
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Compound Information
Molecular Weight:270.2402
Molecular Formula:C14H10N2O4
InChIKey:RXUWVHYGEJQYBF-MDZDMXLPSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:SOTWEFZCIZVKCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:FREKFKRWVDRPHG-CMDGGOBGSA-N
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Compound Information
Molecular Weight:173.007
Molecular Formula:C6H5BrO
InChIKey:MNOJRWOWILAHAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:VOEDRUGFNJEWGQ-VMPITWQZSA-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:238.2812
Molecular Formula:C16H14O2
InChIKey:FPHCHJANYQCPOQ-VAWYXSNFSA-N
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Compound Information
Molecular Weight:222.2372
Molecular Formula:C12H14O4
InChIKey:OPFJHFOFMZFPKX-FNORWQNLSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:CERQOIWHTDAKMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.0344
Molecular Formula:C7H7IO
InChIKey:SYSZENVIJHPFNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:PDNJMHZLMGTCDU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:YNGIFMKMDRDNBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2219
Molecular Formula:C12H12O3
InChIKey:LFADOSKLDCVTKK-BQYQJAHWSA-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:213.2319
Molecular Formula:C13H11NO2
InChIKey:GVXTZYRMZZIIKT-VOTSOKGWSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:NKDGKUQSBGVVDD-AATRIKPKSA-N
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Compound Information
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:KMBQKHKEEHEPOE-AATRIKPKSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:CFUJXLFEFSNRLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.292
Molecular Formula:C11H14O3S
InChIKey:FINGKCDOXDQKBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.1846
Molecular Formula:C10H9NO
InChIKey:APLVPBUBDFWWAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:QZSUDKYHNOUOOX-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:162.2283
Molecular Formula:C11H14O
InChIKey:GVIJAJGHRNIYRL-BQYQJAHWSA-N
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Compound Information
Molecular Weight:273.08
Molecular Formula:C10H9BrO4
InChIKey:XTOBBOGERWXOHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:LKNXCDZIIQHKHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZSPTYLOMNJNZNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.1996
Molecular Formula:C11H11F3O
InChIKey:YWQOPLJHSOZSAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:DVQCXAUFUOFSDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.904
Molecular Formula:C6H4Br2
InChIKey:WQONPSCCEXUXTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:HETCEOQFVDFGSY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.0349
Molecular Formula:C2H2O4
InChIKey:MUBZPKHOEPUJKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:OOXSZTBSOKVISH-KQQUZDAGSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:MHPUKMUPOKHOJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:749.08
Molecular Formula:C40H36O4P2Pd
InChIKey:UVBXZOISXNZBLY-UHFFFAOYSA-L
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Compound Information
Molecular Weight:220.0078
Molecular Formula:C6H5IO
InChIKey:Not Available
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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:172.023
Molecular Formula:C6H6BrN
InChIKey:AOPBDRUWRLBSDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:WOOIWZFSSZZIDE-UHFFFAOYSA-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:148.2017
Molecular Formula:C10H12O
InChIKey:HEPHYCJJLAUKSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.099
Molecular Formula:C7H7BrS
InChIKey:YEUYZNNBXLMFCW-UHFFFAOYSA-N
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