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2-Acetylbenzenecarbonitrile

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2-Acetylbenzenecarbonitrile Basic information
Product Name:2-Acetylbenzenecarbonitrile
Synonyms:2'-CYANOACETOPHENONE;Benzonitrile,2-acetyl-;Benzonitrile, 2-acetyl- (9CI);2-acetylbenzenitrile;2-ACETYLBENZONITRILE;2-Acetylbenzenecarbonitrile
CAS:91054-33-0
MF:C9H7NO
MW:145.16
EINECS:
Product Categories:NITRILE;ACETYLGROUP;Aromatic Nitriles
Mol File:91054-33-0.mol
2-Acetylbenzenecarbonitrile Structure
2-Acetylbenzenecarbonitrile Chemical Properties
Melting point 46-48°C
Boiling point 264.27°C (rough estimate)
density 1.1555 (rough estimate)
refractive index 1.4500 (estimate)
storage temp. Inert atmosphere,Room Temperature
form solid
color Off-white to light yellow
CAS DataBase Reference91054-33-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38-22
Safety Statements 26-36/37/39
RIDADR 3439
HazardClass IRRITANT
HS Code 2926907090
MSDS Information
2-Acetylbenzenecarbonitrile Usage And Synthesis
Synthesis
ZINC CYANIDE

557-21-1

2'-Chloroacetophenone

2142-68-9

2-ACETYLBENZENECARBONITRILE

91054-33-0

Under argon protection, NiCl2-6H2O (0.05 mmol, 11.9 mg), dppf (0.06 mmol, 33.3 mg), Zn (0.2 mmol, 13.0 mg), DMAP (1.0 mmol, 122.2 mg), Zn(CN)2 (0.8 mmol, 93.9 mg), o-chloroacetophenone (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were added to a 25.0 mL sealed tube. The reaction mixture was placed in an oil bath at 60°C for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was filtered directly through a short silica gel column and washed with dichloromethane. The filtrate was concentrated and purified by silica gel column chromatography (wet sampling was used to avoid sample loss). The eluent ratio was petroleum ether/ethyl acetate=20:1, and 117.2 mg of 2-acetylbenzonitrile was obtained as a white solid with 88% yield, and the 1H NMR showed a purity of more than 98%.

References[1] Organic Letters, 2017, vol. 19, # 8, p. 2118 - 2121
[2] Patent: CN108623495, 2018, A. Location in patent: Paragraph 0043; 0045; 0139-0141
2-Acetylbenzenecarbonitrile Preparation Products And Raw materials
Raw materialsZINC CYANIDE-->2'-Chloroacetophenone-->Nickel(II) chloride hexahydrate-->ZINC-->1,1'-Bis(diphenylphosphino)ferrocene-->4-Dimethylaminopyridine-->Acetonitrile
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