Methyl 2-cyanobenzoate

Base Information

• Chemical Name: Methyl 2-cyanobenzoate
• CAS No.: 6587-24-2
• Molecular Formula: C9H7 N O2
• Molecular Weight: 161.16
• Hs Code.: 2926909090
• European Community (EC) Number: 674-134-9
• DSSTox Substance ID: DTXSID80342511
• Nikkaji Number: J126.352H
• Wikidata: Q72489564
• ChEMBL ID: CHEMBL4543803
• Mol file: 6587-24-2.mol

Synonyms:Methyl 2-cyanobenzoate;6587-24-2;Benzoic acid, 2-cyano-, methyl ester;methyl-2-cyanobenzoate;MFCD00016376;Benzoic acid, o-cyano-, methyl ester;METHYL-2-CYANO BENZOATE;METHYL2-CYANOBENZOATE;2-(Methoxycarbonyl)benzonitrile;Methyl o-cyanobenzoate;o-Cyanbenzoesauremethylester;SCHEMBL181067;CHEMBL4543803;DTXSID80342511;2-cyano-benzoic acid methyl ester;CHEBI:194859;AKOS006229429;CS-W005307;FS-1551;SY005784;FT-0628452;EN300-105663;A835258;J-522007;Z1201617254

Chemical Property of Methyl 2-cyanobenzoate

Chemical Property:

• Vapor Pressure: 0.00149mmHg at 25°C
• Melting Point: 47oC
• Boiling Point: 98-100oC(0.2 torr)
• Flash Point: 136.2oC
• PSA: 50.09000
• Density: 1.18g/cm3
• LogP: 1.34488
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-cyanobenzoate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 2-cyanobenzoate

There total 35 articles about Methyl 2-cyanobenzoate 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: 100.0%

2-cyanobenzoic acid (3839-22-3) + methyl iodide (74-88-4) → methyl 2-cyanobenzoate (6587-24-2)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 96h;

DOI:10.1016/j.bmcl.2007.10.060

Reference yield: 99.0%

N-[3-cyano-3-methoxy-1(3H)-isobenzofuranylidene]-2,4,4-trimethyl-2-pentanamine (1449007-80-0) → 1,1,3,3-tetramethylbutane isonitrile (14542-93-9) + methyl 2-cyanobenzoate (6587-24-2)

Guidance literature:

With tris(pentafluorophenyl)borate; In tetrahydrofuran; at 70 ℃; for 8h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol5026519

Reference yield: 98.0%

phthalamic acid (88-97-1) + methyl chloroformate (79-22-1) → methyl 2-cyanobenzoate (6587-24-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1007/s00706-018-2293-9

upstream raw materials:

2-carbomethoxyaniline

Methyl-tert.-butylperoxyoxalat

benzonitrile

o-iodo-methyl-benzoic acid

Downstream raw materials:

2-cyano-N,N-dimethylbenzamide

methyl 2-<3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl>-benzoate

2-cyanobenzoic acid

isoindole-1,3-dione mono-dimethylhydrazone

Refernces

• 1、 Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min. "Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction". . p. 5691 - 5701. Retrieved 2020/04/10.
• 2、 Mata, Alejandro,Hone, Christopher A.,Gutmann, Bernhard,Moens, Luc,Kappe, C. Oliver. "Continuous-Flow Pd-Catalyzed Carbonylation of Aryl Chlorides with Carbon Monoxide at Elevated Temperature and Pressure". . p. 997 - 1001. Retrieved 2019/01/24.