2-Cyano-N,N-dimethylbenzamide

Base Information

• Chemical Name: 2-Cyano-N,N-dimethylbenzamide
• CAS No.: 26487-08-1
• Molecular Formula: C10H10 N2 O
• Molecular Weight: 174.202
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00526215
• Nikkaji Number: J2.208.521B
• Wikidata: Q82394476
• Mol file: 26487-08-1.mol

Synonyms:2-CYANO-N,N-DIMETHYLBENZAMIDE;26487-08-1;2-CYANO-N,N-DIMETHYL-BENZAMIDE;2-cyano-N, N-dimethylbenzamide;DTXSID00526215;AKOS006330023

Chemical Property of 2-Cyano-N,N-dimethylbenzamide

Chemical Property:

• Vapor Pressure: 2.61E-05mmHg at 25°C
• Refractive Index: 1.556
• Boiling Point: 358.1°C at 760 mmHg
• Flash Point: 170.4°C
• PSA: 44.10000
• Density: 1.13g/cm³
• LogP: 1.26008
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 174.079312947
• Heavy Atom Count: 13
• Complexity: 239

Purity/Quality:

99%min ^*data from raw suppliers

2-Cyano-N,N-dimethylbenzamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Cyano-N,N-dimethylbenzamide

There total 7 articles about 2-Cyano-N,N-dimethylbenzamide 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: 93.0%

2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile (214360-47-1) + N,N-Dimethylcarbamoyl chloride (79-44-7) → 2-cyano-N,N-dimethylbenzamide (26487-08-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride; In tetrahydrofuran; at 80 ℃; for 16h;

DOI:10.1021/jo050459h

Reference yield: 70.0%

o-formylbenzonitrile (7468-67-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-cyano-N,N-dimethylbenzamide (26487-08-1)

Guidance literature:

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In 1,1,2-trichloroethane; water; at 90 ℃; for 24h;

DOI:10.1002/anie.201108763

Reference yield: 67.0%

N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) + N,N-dimethylbenzamide (611-74-5) → 2-cyano-N,N-dimethylbenzamide (26487-08-1)

Guidance literature:

With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; sodium acetate; In 1,2-dichloro-ethane; at 120 ℃; for 24h; chemoselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1039/c3cc49502g

upstream raw materials:

methyl 2-cyanobenzoate

dimethyl amine

2-Cyanobenzoyl chloride

2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile

Refernces

• 1、 Liu, Weiping,Ackermann, Lutz. "Versatile ruthenium(ii)-catalyzed C-H cyanations of benzamides". supporting information. p. 1878 - 1881. Retrieved 2014/02/14.
• 2、 Lysen, Morten,Kelleher, Susan,Begtrup, Mikael,Kristensen, Jesper Langgaard. "Synthesis of tertiary benzamides via Pd-catalyzed coupling of arylboronic esters and carbamoyl chlorides". . p. 5342 - 5343. Retrieved 2007/10/03.