3-Acetylbenzonitrile

Base Information

• Chemical Name: 3-Acetylbenzonitrile
• CAS No.: 6136-68-1
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29269090
• European Community (EC) Number: 228-110-6
• NSC Number: 210360
• UNII: TSJ72034P9
• DSSTox Substance ID: DTXSID50210273
• Nikkaji Number: J227.317I
• Wikidata: Q27290250
• ChEMBL ID: CHEMBL4544662
• Mol file: 6136-68-1.mol

Synonyms:3-Acetylbenzonitrile;6136-68-1;3'-Cyanoacetophenone;m-Cyanoacetophenone;Benzonitrile, 3-acetyl-;3-acetyl-benzonitrile;UNII-TSJ72034P9;TSJ72034P9;EINECS 228-110-6;MFCD00001806;NSC-210360;3-cyanoacetophenone;3-acetylbenzenecarbonitrile;m-acetylbenzonitrile;NSC210360;3-acetyl benzonitrile;3-Acetylbenzonitrile, 97%;SCHEMBL39137;3-CN-C6H4-COCH3;CHEMBL4544662;DTXSID50210273;CHEBI:194596;3-CYANOPHENYL METHYL KETONE;STR03196;AM1099;BBL100017;STL510972;AKOS007930840;CS-W004403;NSC 210360;PS-4054;AC-26105;SY002919;C1993;FT-0615550;EN300-37505;A21000;W-111725;Q27290250;Z381541056

Chemical Property of 3-Acetylbenzonitrile

Chemical Property:

• Appearance/Colour: pale yellowish-orange to brown powder
• Melting Point: 98-100 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 267.3 °C at 760 mmHg
• Flash Point: 115.5 °C
• PSA: 40.86000
• Density: 1.11 g/cm³
• LogP: 1.76088
• Storage Temp.: Store below +30°C.
• Solubility.: 4g/l
• Water Solubility.: Insoluble in water.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 201

Purity/Quality:

98%,99%, ^*data from raw suppliers

m-Cyanoacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC=CC(=C1)C#N
• Uses: 3-Acetylbenzonitrile has been used in the preparation of 3-(hydroxyacetyl)benzonitrile, and 3-(1-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenylimino)ethyl)benzonitrile. Preparation of (q2-2-Acetyl-4-cyanophenyl)tetra- carbonylmanganese by Reaction of 3-Acetylbenzonitrile with Benzylpentacarbonylmanganese. Four aromatic amidoximes were synthesized by reacting hydroxylamine with 1,3 -dicyanobenzene, 1,4- dicyanobenzene, 3-acetylbenzonitrile, and 4-acetylbenzonitrile. Darzens condensation of 3-acetylbenzonitrile provided aldehyde. 3-Acetylbenzonitrile has been used in the preparation of: 3-(hydroxyacetyl)benzonitrile3-(1-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenylimino)ethyl)benzonitrile

Technology Process of 3-Acetylbenzonitrile

There total 40 articles about 3-Acetylbenzonitrile 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: 99.0%

sodium cyanide (773837-37-9) + 1-(3-Bromophenyl)ethanone (2142-63-4) → 3-acethylbenzonitrile (6136-68-1)

Guidance literature:

With calcium dihydride; tri-tert-butyl phosphine; [Pd₂(dba)5]; In tetrahydrofuran; acetonitrile; at 70 ℃; for 2h;

DOI:10.1021/ja2042035

Reference yield: 96.0%

zinc(II) cyanide (557-21-1) + 3'-iodoacetophenone (14452-30-3) → 3-acethylbenzonitrile (6136-68-1)

Guidance literature:

palladium diacetate; PS-triphenylphosphine; In N,N-dimethyl-formamide; at 140 ℃; for 0.5h; Irradiation; microwave;

DOI:10.1016/j.tetlet.2004.09.184

Reference yield: 95.0%

potassiumhexacyanoferrate(II) trihydrate + 1-(3-Bromophenyl)ethanone (2142-63-4) → 3-acethylbenzonitrile (6136-68-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; tert-butyl alcohol; at 85 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c2cc17468e

upstream raw materials:

1-(3-aminophenyl)ethanone

m-cyanovalerophenone

3-(1-Methoxyimino-ethyl)-benzonitrile

diazomethane

Downstream raw materials:

4-Benzyloxy-3'-cyan-chalkon

3-acetylbenzenecarboximidimic acid ethyl ester hydrochloride

3-(prop-1-en-2-yl)benzonitrile

acetophenone

Refernces

• 1、 Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu. "Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions". . p. 12344 - 12353. Retrieved 2021/09/02.
• 2、 Alshakova, Iryna D.,Nikonov, Georgii I.. "Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex". . p. 5370 - 5378. Retrieved 2019/06/14.