4-Chlorobenzoyl cyanide

Base Information

• Chemical Name: 4-Chlorobenzoyl cyanide
• CAS No.: 13014-48-7
• Molecular Formula: C8H4 Cl N O
• Molecular Weight: 165.579
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID80431439
• Nikkaji Number: J757.620J
• Wikidata: Q82245314
• Mol file: 13014-48-7.mol

Synonyms:4-chlorobenzoyl cyanide;13014-48-7;(4-CHLORO-PHENYL)-OXO-ACETONITRILE;4-chlorobenzoylcyanide;2-(4-chlorophenyl)-2-oxoacetonitrile;p-chlorobenzoylcyanide;4-chloro-benzoylcyanide;4-chlorophenylglyoxylonitrile;SCHEMBL1322525;UDBBCXDMJVNFLI-UHFFFAOYSA-;DTXSID80431439;UDBBCXDMJVNFLI-UHFFFAOYSA-N;AB1327;MFCD06658396;AKOS006283418;SB32679;(4-CHLOROPHENYL)OXO-ACETONITRILE;AS-44561;BB 0260549;CS-0208499;EN300-69455;2-(4-chlorophenyl)-2-oxidanylidene-ethanenitrile;A806026;F2167-4724;InChI=1/C8H4ClNO/c9-7-3-1-6(2-4-7)8(11)5-10/h1-4H

Chemical Property of 4-Chlorobenzoyl cyanide

Chemical Property:

• PSA: 40.86000
• LogP: 2.04628
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.9981414
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

98%Min ^*data from raw suppliers

(4-Chloro-phenyl)-oxo-acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)C#N)Cl

Technology Process of 4-Chlorobenzoyl cyanide

There total 28 articles about 4-Chlorobenzoyl cyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

copper(I) cyanide (544-92-3) + 4-chloro-benzoyl chloride (122-01-0) → 4-chlorobenzoyl cyanide (13014-48-7)

Guidance literature:

In acetonitrile; for 0.5h; Heating;

DOI:10.1002/anie.200453696

Reference yield: 93.0%

(+/-)-2-(4-chlorophenyl)-2-(trimethylsiloxy)-acetonitrile (66985-46-4) → 4-chlorobenzoyl cyanide (13014-48-7)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; at 40 ℃; for 4h; Irradiation; indirect daylight;

Reference yield: 92.0%

4-chlorophenylglyoxal (4998-15-6) → 4-chlorobenzoyl cyanide (13014-48-7)

Guidance literature:

With 1-amino-2-oxo-4,6-diphenylpyridine; In toluene; at 110 ℃; for 6h;

DOI:10.1055/s-1980-29233

upstream raw materials:

p-chloro-2-(hydroxyimino)-2-phenylacetonitrile

(4-chloro-phenyl)-(4-dimethylamino-phenylimino)-acetonitrile

carbonyl cyanide

chlorobenzene

Downstream raw materials:

2-amino-1-(4-chlorophenyl)ethanol

ethyl 2-(4-chlorophenyl)-2-oxoacetate

p-chlorobenzoylmalononitrile

N-(α-Cyan-4-chlor-benzyliden)-N'-diaminomethylen-hydrazin

Refernces

• 1、 Xiong, Meijun,Yu, Shasha,Xie, Xin,Li, Shi,Liu, Yuanhong. "Reactions of Zirconocene-1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles". . p. 5597 - 5601. Retrieved 2015.
• 2、 Sukata, Kazuaki. "Reaction of Aromatic Acyl Chlorides with Potassium or Sodium Cyanide Impregnated onto Amberlite XAD Resins. Efficient Synthesis of Aromatic Acyl Cyanides". . p. 1085 - 1090. Retrieved 1987.
• 3、 Ando, Takashi,Kawate, Takehiko,Yamawaki, Junko,Hanafusa, Terukiyo. "Efficient Sonochemical Synthesis of Aromatic Acyl Cyanides". . p. 637 - 638. Retrieved 1983.
• 4、 Macias-Ruvalcaba, Norma A.,Evans, Dennis H.. "Quantitative evaluation of the mechanism of electroreduction of benzoyl cyanides". . p. 589 - 594. Retrieved 2007.
• 5、 -. "Novel synthesis method of alpha-carbonyl acid ester". . . Retrieved 2020/07/21.
• 6、 Kim, Kicheol,Moeljadi, Adhitya Mangala Putra,Hirao, Hajime,Hong, Soon Hyeok. "Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex". . p. 3292 - 3298. Retrieved 2017/09/06.