Methyl 2-chloro-5-cyanobenzoate

Base Information

• Chemical Name: Methyl 2-chloro-5-cyanobenzoate
• CAS No.: 914106-36-8
• Molecular Formula: C9H6ClNO2
• Molecular Weight: 195.605
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID60586557
• Mol file: 914106-36-8.mol

Synonyms:methyl 2-chloro-5-cyanobenzoate;914106-36-8;Benzoic acid, 2-chloro-5-cyano-, methyl ester;2-Chloro-5-cyanobenzoicacid Methyl ester;2-chloro-5-cyano-benzoic acid methyl ester;methyl2-chloro-5-cyanobenzoate;SCHEMBL1179997;DTXSID60586557;RGLQGCVEXOWXEK-UHFFFAOYSA-N;AMY42551;MFCD13192027;AKOS022189772;AS-60712;DA-01076;2-Chloro-5-cyanobenzoic acid methyl ester;CS-0046257

Chemical Property of Methyl 2-chloro-5-cyanobenzoate

Chemical Property:

• Melting Point: 100-103℃
• PSA: 50.09000
• LogP: 1.99828
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 195.0087061
• Heavy Atom Count: 13
• Complexity: 245

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-chloro-5-cyanobenzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Methyl 2-chloro-5-cyanobenzoate

There total 3 articles about Methyl 2-chloro-5-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: 94.0%

methanol (67-56-1) + 2-chloro-5-cyanobenzoic acid (89891-83-8) → 2-chloro-5-cyanobenzoic acid methyl ester (914106-36-8)

Guidance literature:

With dicyclohexyl-carbodiimide; dmap; In dichloromethane; at 0 - 25 ℃;

DOI:10.1021/jm0612867

Reference yield:

2-chloro-5-aminobenzoic acid (89-54-3) → 2-chloro-5-cyanobenzoic acid methyl ester (914106-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaNO₂; aq. HCl

1.2: KCN

2.1: 94 percent / 1,3-dicyclohexylcarbodiimide / 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 25 °C

With hydrogenchloride; dicyclohexyl-carbodiimide; sodium nitrite; dmap; In dichloromethane; 1.2: Sandmeyer reaction;

DOI:10.1021/jm0612867

Reference yield:

2-chloro-5-iodobenzoic acid (19094-56-5) → 2-chloro-5-cyanobenzoic acid methyl ester (914106-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 8 h / Reflux

2: L-proline / N,N-dimethyl-formamide / 11 h / 70 - 100 °C

With sulfuric acid; L-proline; In N,N-dimethyl-formamide;

DOI:10.3390/molecules25153500

upstream raw materials:

methanol

2-chloro-5-cyanobenzoic acid

2-chloro-5-aminobenzoic acid

2-chloro-5-iodobenzoic acid

Downstream raw materials:

4-chloro-3-formylbenzonitrile

Refernces

• 1、 Dai, Li,Liu, Xing-Hai,Ma, Tian-Yang,Mei, Jun-Chang,Ren, Chao-Li,Tan, Cheng-Xia,Tian, Xiao-Yu,Yang, Sen. "Synthesis and biological activity of benzamides substituted with pyridine-linked 1,2,4-oxadiazole". . . Retrieved 2020/08/28.
• 2、 Patrick, Donald A.,Bakunov, Stanislav A.,Bakunova, Svetlana M.,Kumar, E.V.K. Suresh,Lombardy, Richard J.,Jones, Susan Kilgore,Bridges, Arlene S.,Zhirnov, Oksana,Hall, James Edwin,Wenzler, Tanja,Brun, Reto,Tidwell, Richard R.. "Synthesis and in vitro antiprotozoal activities of dicationic 3,5-diphenylisoxazoles". . p. 2468 - 2485. Retrieved 2008/02/03.