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115959

Sigma-Aldrich

Benzoyl cyanide

98%

Synonym(s):

Phenylglyoxylonitrile

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About This Item

Linear Formula:
C6H5COCN
CAS Number:
613-90-1
Molecular Weight:
131.13
Beilstein/REAXYS Number:
1072101
EC Number:
210-359-7
MDL number:
MFCD00001837
UNSPSC Code:
12352100
PubChem Substance ID:
24847253
NACRES:
NA.22

assay

98%

form

solid

bp

206 °C (lit.)

mp

28-31 °C (lit.)

density

1.106 g/mL at 25 °C (lit.)

functional group

ketone
nitrile
phenyl

SMILES string

O=C(C#N)c1ccccc1

InChI

1S/C8H5NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H

InChI key

GJQBHOAJJGIPRH-UHFFFAOYSA-N

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General description

Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by Rhodococcus sp. CCZU10-1 to form benzoylformic acid.

Application

Reagent for selective acylation of amino compounds.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

183.2 °F - closed cup

flash_point_c

84 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF4613
MKCD2518
MKBX0451V
MKBP4311V
STBC4241V

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Synthesis, 433-433 (1993)
Weisi Xiong et al.
Biotechnology letters, 37(8), 1703-1709 (2015-04-22)
To develop a biphasic system for use in plant tissue-mediated biotransformations to overcome the low water solubilities of substrates and inhibitory effects of products. Commonly-used organic solvents and ionic liquid were assayed using the biphasic system to reduce water-insoluble benzoyl
Yi Xu et al.
Journal of virology, 92(11) (2018-03-09)
Translational readthrough of the stop codon of the capsid protein (CP) open reading frame (ORF) is used by members of the Luteoviridae to produce their minor capsid protein as a readthrough protein (RTP). The elements regulating RTP expression are not
Petar I Penev et al.
Genome biology and evolution, 12(10), 1694-1710 (2020-08-14)
The ribosome's common core, comprised of ribosomal RNA (rRNA) and universal ribosomal proteins, connects all life back to a common ancestor and serves as a window to relationships among organisms. The rRNA of the common core is similar to rRNA
Norma A Macías-Ruvalcaba et al.
The Journal of organic chemistry, 72(2), 589-594 (2007-01-16)
The mechanism of reduction of benzoyl cyanide, 6, p-methoxybenzoyl cyanide, 7, and p-chlorobenzoyl cyanide, 8, has been studied in acetonitrile (6 and 7), N,N-dimethylformamide (6), and acetonitrile containing water (all three compounds). The reaction proceeds by initial reduction to form
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