PYRUVONITRILE

Base Information

• Chemical Name: PYRUVONITRILE
• CAS No.: 631-57-2
• Molecular Formula: C3H3 N O
• Molecular Weight: 69.0629
• European Community (EC) Number: 211-159-2
• NSC Number: 91482
• UNII: ULO441649V
• DSSTox Substance ID: DTXSID10212430
• Nikkaji Number: J6.893D
• Wikipedia: Acetyl_cyanide
• Wikidata: Q15738374
• Mol file: 631-57-2.mol

Synonyms:Pyruvonitrile(6CI,7CI,8CI); 2-Oxopropanenitrile; 2-Oxopropionitrile; Acetyl cyanide; NSC91482; Pyruvic acid nitrile; a-Oxopropionitrile

Chemical Property of PYRUVONITRILE

Chemical Property:

• Vapor Pressure: 51.9mmHg at 25°C
• Refractive Index: n20/D 1.376(lit.)
• Boiling Point: 92-93 °C(lit.)
• Flash Point: 58 °F
• PSA: 40.86000
• Density: 0.974 g/mL at 25 °C(lit.)
• LogP: 0.09898
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ether and acetonitrile.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 69.021463719
• Heavy Atom Count: 5
• Complexity: 86.3

Purity/Quality:

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

Pyruvonitrile(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T,N
• Hazard Codes: F,T,N
• Statements: 11-23/25-51/53-37/38
• Safety Statements: 45-61-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(=O)C#N
• Uses: Pyruvonitrile was used in the synthesis of cuprate-carbonyl π-complexes by reaction with Me2CuLi in THF.

Technology Process of PYRUVONITRILE

There total 50 articles about PYRUVONITRILE 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: 96.0%

bis(dimethylamino)malononitrile (63442-64-8) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2) + 1,1-dicyanoethyl acetate (7790-01-4) + Cyan-N,N,N',N'-tetramethylformamidinium-chlorid (70976-82-8)

Guidance literature:

In diethyl ether; for 6h; Ambient temperature;

Reference yield: 90.0%

trimethylsilyl cyanide (7677-24-9) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2)

Guidance literature:

With zinc(II) iodide; at 100 ℃; for 2h; Inert atmosphere; Neat (no solvent); neat (no solvent);

DOI:10.2174/157017809790442916

Reference yield: 88.0%

methyl 2-oxo-2-phenylacetate (15206-55-0) + ethyl cyanoformate (623-49-4) → Acetyl cyanide (631-57-2)

Guidance literature:

With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/cjoc.201500399

upstream raw materials:

pyridine

hydrogen cyanide

acetyl chloride

Ketene

Downstream raw materials:

1,1-dicyanoethyl acetate

2,2-bis-(1-methyl-2-phenyl-indol-3-yl)-propionitrile

2,2-bis-(1,2-diphenyl-indol-3-yl)-propionitrile

1-acetyl-2-phenylhydrazine

Refernces

• 1、 -. "Novel synthesis method of alpha-carbonyl acid ester". Paragraph 0016; 0050; 0053. . Retrieved 2020/07/21.
• 2、 Zeng, Wei,Yang, Jingya,Meng, Bo,Zhang, Bo,Jiang, Mingzhe,Chen, Fu-Xue. "ZnI2-catalyzed cyanation of acyl chlorides with TMS-CN: An interesting role of iodine". experimental part. p. 637 - 641. Retrieved 2010/06/15.