Standard Article

Acetonitrile

  1. Roger Bishop1,
  2. Debatosh Majumdar2,
  3. Geert-Jan Boons2

Published Online: 15 OCT 2004

DOI: 10.1002/047084289X.ra017.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Bishop, R., Majumdar, D. and Boons, G.-J. 2004. Acetonitrile. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    The University of New South Wales, Kensington, NSW, Australia

  2. 2

    Complex Carbohydrate Research Center, University of Georgia, Athens, GA, USA

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

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[75-05-8] C2H3N (MW 41.05)

(solvent for inorganic and organometallic reagents; undergoes addition reactions to nitrile group; anion is nucleophilic reagent; Ritter reaction reagent; oxidizing agent in combination with H2O2)

Alternate Name: methyl cyanide; ethanenitrile; cyanomethane.

Physical Data: mp −45 °C; bp 81.6 °C; d 0.787 g cm−3 (20 °C).

Solubility: miscible with water and most organic solvents (but not petroleum); forms constant boiling mixture containing 16% water, bp 76 °C.

Form Supplied in: colorless liquid; widely available.

Drying: fractional distillation from CaH2 or P2O5.

Analysis of Reagent Purity: GLC; HPLC grade (99.9+% purity) commercially available.

Handling, Storage, and Precautions: flammable volatile liquid; keep dry; toxic vapor; mild lachrymator; possible skin irritant; evolves toxic fumes if heated to decomposition; incompatible with fuming HNO3, N2O4/In, 2-cyano-2-propylnitrate, ClF/F2, Cl3HSi/diphenyl sulfoxide, metal perchlorates, HClO4, fuming H2SO4, heat/conc. H2SO4, and N-fluoro compounds.2

Featured Compounds

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  1. 1 - 124
Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:FFFMSANAQQVUJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.092
Molecular Formula:C10H10Cl2
InChIKey:HYMZFDHPPPULEO-MDZDMXLPSA-N
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Compound Information
Molecular Weight:134.452
Molecular Formula:Cl2Cu
InChIKey:ORTQZVOHEJQUHG-UHFFFAOYSA-L
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Compound Information
Molecular Weight:42.394
Molecular Formula:ClLi
InChIKey:KWGKDLIKAYFUFQ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.544
Molecular Formula:C10H10ClI
InChIKey:OCMCFVMERISQGX-MDZDMXLPSA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1038
Molecular Formula:C4H6N2
InChIKey:CSIFGMFVGDBOQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.3746
Molecular Formula:C6H18NNaSi2
InChIKey:WRIKHQLVHPKCJU-UHFFFAOYSA-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:123.1558
Molecular Formula:C6H9N3
InChIKey:BJJDXAFKCKSLTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.1322
Molecular Formula:CH3KO
InChIKey:BDAWXSQJJCIFIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.59
Molecular Formula:C2H2CuN
InChIKey:KUPMQQROGQMVCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.146
Molecular Formula:C10H17Br
InChIKey:JSCUZAYKVZXKQE-JXMROGBWSA-N
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:JJNRLLWEOZKYJE-XYOKQWHBSA-N
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Compound Information
Molecular Weight:63.0337
Molecular Formula:C2H2NNa
InChIKey:AJNYBQJALNOVGN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:MTZQAGJQAFMTAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.158
Molecular Formula:C9H7NO
InChIKey:ZJRCIQAMTAINCB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:RTLKJCSGNBYCKJ-UHFFFAOYSA-N
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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:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-QPJJXVBHSA-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:147.1739
Molecular Formula:C9H9NO
InChIKey:Not Available
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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:126.11
Molecular Formula:C6H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:168.1467
Molecular Formula:C8H8O4
InChIKey:XLEYFDVVXLMULC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.581
Molecular Formula:C4H10ClNO
InChIKey:WGMHMVLZFAJNOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.543
Molecular Formula:C2H7ClN2
InChIKey:WCQOBLXWLRDEQA-UHFFFAOYSA-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:162.2267
Molecular Formula:C8H18O3
InChIKey:NDQXKKFRNOPRDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.028
Molecular Formula:C5H9BrO2
InChIKey:ARFLASKVLJTEJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:FNENWZWNOPCZGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:65.409
Molecular Formula:Zn
InChIKey:HCHKCACWOHOZIP-UHFFFAOYSA-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:61.0831
Molecular Formula:C2H7NO
InChIKey:HZAXFHJVJLSVMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.1045
Molecular Formula:C4H7NO
InChIKey:GUXJXWKCUUWCLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.499
Molecular Formula:C4H6CdO4
InChIKey:LHQLJMJLROMYRN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:MSHFRERJPWKJFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:VGCSNHYGZYURJQ-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:150.2176
Molecular Formula:C10H14O
InChIKey:YEYBYPNZUQHDMO-DTORHVGOSA-N
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Compound Information
Molecular Weight:209.2848
Molecular Formula:C12H19NO2
InChIKey:QGQQCWHALQYFDK-IWDIQUIJSA-N
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Compound Information
Molecular Weight:42.0797
Molecular Formula:C3H6
InChIKey:QQONPFPTGQHPMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1445
Molecular Formula:C5H10N2O3
InChIKey:ZIJGNUQMMAYGAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.81
Molecular Formula:BF4NO2
InChIKey:RGVZMPONLYFINH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.604
Molecular Formula:C6H11ClO
InChIKey:JMNYJOWPUIPWJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.1949
Molecular Formula:C8H13NO
InChIKey:SVTLEEXYUSJVCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.52
Molecular Formula:Cl4Sn
InChIKey:Not Available
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-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:150.2176
Molecular Formula:C10H14O
InChIKey:LYPNJXCOOQMUMY-NXEZZACHSA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:QXDMTZUIVJYCCS-LGUIWLBCSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:UPGHEUSRLZSXAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:MTXQFIBTASMPHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.0514
Molecular Formula:C2H4O3
InChIKey:Not Available
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:IYKQSWOXMSYYMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:272.2512
Molecular Formula:C12H16O7
InChIKey:LLPWGHLVUPBSLP-IJLUTSLNSA-N
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Compound Information
Molecular Weight:376.2762
Molecular Formula:C12H16N4O10
InChIKey:ZJRHNHIEORAKEY-RMPHRYRLSA-N
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Compound Information
Molecular Weight:376.2762
Molecular Formula:C12H16N4O10
InChIKey:ZJRHNHIEORAKEY-ZIQFBCGOSA-N
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Compound Information
Molecular Weight:372.3306
Molecular Formula:C14H20N4O8
InChIKey:RCZQZPRGYCLVJZ-RGDJUOJXSA-N
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Compound Information
Molecular Weight:548.222
Molecular Formula:CeH8N8O18
InChIKey:QHFIXWIXXKDUKT-UHFFFAOYSA-P
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Compound Information
Molecular Weight:65.0099
Molecular Formula:N3Na
InChIKey:PXIPVTKHYLBLMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:719.8633
Molecular Formula:C47H45NO6
InChIKey:GLJIELLDFCAQFU-JJJHRABCSA-N
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Compound Information
Molecular Weight:564.6906
Molecular Formula:C36H38NO5
InChIKey:UGZBIWNXOSXWKN-GJXDWMKPSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:IKCLCGXPQILATA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:720.249
Molecular Formula:C43H42ClNO7
InChIKey:UAHUREOFUVTUHN-BBZGLCMASA-N
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Compound Information
Molecular Weight:720.249
Molecular Formula:C43H42ClNO7
InChIKey:NVDMOAJGRDPYSX-ABYWANGZSA-N
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Compound Information
Molecular Weight:678.212
Molecular Formula:C41H40ClNO6
InChIKey:WCUQORIOKJBVHL-GCKSPRBUSA-N
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Compound Information
Molecular Weight:54.0237
Molecular Formula:CH3NaO
InChIKey:WQDUMFSSJAZKTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:521.535
Molecular Formula:C21H31NO12S
InChIKey:VUDPJAWMOISBAC-KUHALTKMSA-N
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Compound Information
Molecular Weight:258.303
Molecular Formula:C4H10F3O3S3
InChIKey:TXVLFCLSVCYBIV-UHFFFAOYSA-M
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Compound Information
Molecular Weight:568.635
Molecular Formula:C22H34NO12S2
InChIKey:CHQPFAPFVNNGPI-HWIXJMTNSA-O
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Compound Information
Molecular Weight:648.44
Molecular Formula:C21H31INO12S
InChIKey:HDGUUJLJMUSNNZ-HNAMPBBESA-O
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Compound Information
Molecular Weight:224.9845
Molecular Formula:C4H4INO2
InChIKey:LQZMLBORDGWNPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.077
Molecular Formula:CHF3O3S
InChIKey:ITMCEJHCFYSIIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:623.505
Molecular Formula:C21H29F3NO15S
InChIKey:VHIDYUMGSJUSQC-PCZPCTFESA-N
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Compound Information
Molecular Weight:515.4877
Molecular Formula:C22H31N2O12
InChIKey:WTIZCJBURIKBLP-QDRUEPRISA-O
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Compound Information
Molecular Weight:515.4877
Molecular Formula:C22H31N2O12
InChIKey:WTIZCJBURIKBLP-ZJGVECAJSA-O
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:540.646
Molecular Formula:C34H36O6
InChIKey:OGOMAWHSXRDAKZ-BKJHVTENSA-N
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Compound Information
Molecular Weight:473.5601
Molecular Formula:C29H31NO5
InChIKey:IOSTWILXMJCWCW-RQKPWJHBSA-N
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Compound Information
Molecular Weight:210.0314
Molecular Formula:C4F6O3
InChIKey:QAEDZJGFFMLHHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:492.5834
Molecular Formula:C29H33NO6
InChIKey:DDCVEIWUAFGSNJ-RQKPWJHBSA-O
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Compound Information
Molecular Weight:1.00794
Molecular Formula:H
InChIKey:GPRLSGONYQIRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:492.5834
Molecular Formula:C29H33NO6
InChIKey:DDCVEIWUAFGSNJ-XYPQWYOHSA-O
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Compound Information
Molecular Weight:685.033
Molecular Formula:C36H36Cl3NO6
InChIKey:LMICALCPRSCSMO-BKJHVTENSA-N
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Compound Information
Molecular Weight:464.5501
Molecular Formula:C28H32O6
InChIKey:Not Available
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:FLOIPOSVHDNCRB-KJBGKYNMSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:FLOIPOSVHDNCRB-WWBLMGCDSA-N
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Compound Information
Molecular Weight:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:464.5501
Molecular Formula:C28H32O6
InChIKey:UFTIKUYXMPCFQZ-QLHPUIKHSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:MZANRTJUCFQKRB-WWBLMGCDSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:MZANRTJUCFQKRB-KJBGKYNMSA-N
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Compound Information
Molecular Weight:685.033
Molecular Formula:C36H36Cl3NO6
InChIKey:LMICALCPRSCSMO-HSDAUYOJSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:FLOIPOSVHDNCRB-SYMFSADXSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:FLOIPOSVHDNCRB-VRHJCYKTSA-N
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Compound Information
Molecular Weight:608.7631
Molecular Formula:C39H44O6
InChIKey:UJKZBFGKKCLGDY-GFRPZHATSA-N
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Compound Information
Molecular Weight:177.984
Molecular Formula:C4H4BrNO2
InChIKey:PCLIMKBDDGJMGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:542.6371
Molecular Formula:C34H35FO5
InChIKey:QNXIKNZDQVSBCO-BGSSSCFASA-N
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Compound Information
Molecular Weight:104.0791
Molecular Formula:F4Si
InChIKey:ABTOQLMXBSRXSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:580.7099
Molecular Formula:C37H40O6
InChIKey:WDFOSQZERHEEHW-KHKVHWIZSA-N
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Compound Information
Molecular Weight:580.7099
Molecular Formula:C37H40O6
InChIKey:WDFOSQZERHEEHW-WNRBQEJJSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:FLOIPOSVHDNCRB-XNJBDIMCSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:FLOIPOSVHDNCRB-YVBUOIBJSA-N
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Compound Information
Molecular Weight:584.765
Molecular Formula:C36H40O5S
InChIKey:NRALMNQUAKWSMF-GJXDWMKPSA-N
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Compound Information
Molecular Weight:464.5501
Molecular Formula:C28H32O6
InChIKey:Not Available
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:XGUQGDPCAPRZDC-WWBLMGCDSA-N
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Compound Information
Molecular Weight:987.1808
Molecular Formula:C62H66O11
InChIKey:XGUQGDPCAPRZDC-KJBGKYNMSA-N
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Compound Information
Molecular Weight:632.808
Molecular Formula:C40H40O5S
InChIKey:IKCMSYGNAFDJNX-DTQLOPILSA-N
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Compound Information
Molecular Weight:305.13
Molecular Formula:C7H5F3O3SSe
InChIKey:WSBBSYJIJBSMBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:674.7627
Molecular Formula:C38H47N2O7P
InChIKey:RTYAYXUZHPWJOK-JTDOPDNRSA-N
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Compound Information
Molecular Weight:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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