613-90-1 Usage
Chemical Properties
yellow to brown low melting mass
uses
Using benzoyl cyanide as an electrophile also gives selective acylation of the 3-position, as does levulinic acid in the presence of DCC.
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. Reagent for selective acylation of amino compounds.
Uses
Reagent for selective acylation of amino compounds.
Preparation
Benzoyl cyanide is prepared by treatment of benzoyl chloride with sodium cyanide under phase-transfer catalytic conditions. This process is also used to convert 4-methyl, 4-methoxy, and 4-chlorobenzoyl chlorides into the corresponding benzoyl cyanides, and similarly cinnamoyl chloride into cinnamoyl cyanide (98%).
Synthesis Reference(s)
Synthetic Communications, 15, p. 849, 1985 DOI: 10.1080/00397918508063881
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.
Check Digit Verification of cas no
The CAS Registry Mumber 613-90-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 3 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 613-90:
(5*6)+(4*1)+(3*3)+(2*9)+(1*0)=61
61 % 10 = 1
So 613-90-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H5NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H
613-90-1Relevant articles and documents
Selective Monohydrocyanation of Diimine using Potassium Hexacyanoferrate(II)-Benzoyl Chloride Reagent System as a Cyanide Source
Li, Zheng,Wen, Fei,Yang, Jingya
, p. 1849 - 1853 (2016)
The selective monohydrocyanation of diimines using potassium hexacyanoferrate(II)-benzoyl chloride reagent system as a cyanide source under catalyst-free condition is described. The advantages of this protocol are the non-toxic, non-volatile and inexpensive cyanide source, high yield, and simple work-up procedure. [Figure not available: see fulltext.]
Sachs,Whittaker
, p. 501 (1901)
Palladium-catalyzed decarbonylative cyanation of acyl fluorides and chlorides
Sakurai, Shun,Tobisu, Mamoru
supporting information, (2021/01/25)
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Thiocyanate radical mediated dehydration of aldoximes with visible light and air
Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang
supporting information, p. 9701 - 9704 (2019/08/15)
We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.