Methyl 2-cyano-5-methoxybenzoate

Base Information

• Chemical Name: Methyl 2-cyano-5-methoxybenzoate
• CAS No.: 127510-95-6
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50438177
• Nikkaji Number: J2.692.789G
• Wikidata: Q82253825
• Mol file: 127510-95-6.mol

Synonyms:127510-95-6;METHYL 2-CYANO-5-METHOXYBENZOATE;2-Cyano-5-methoxybenzoic acid methyl ester;Methyl 2-cyano-5-methoxy-benzoate;2-cyano-5-methoxy-benzoic acid methyl ester;BENZOIC ACID, 2-CYANO-5-METHOXY-, METHYL ESTER;SCHEMBL4316682;DTXSID50438177;YIRZMMZVHCFIAK-UHFFFAOYSA-N;CFA51095;MFCD09800435;AKOS006328181;MB07668;SB32613;AS-37462;CS-0150501;FT-0738245;Ethyl 3-(2-bromo-4-methoxyphenyl)-2-cyanopropanoate

Chemical Property of Methyl 2-cyano-5-methoxybenzoate

Chemical Property:

• Vapor Pressure: 8.73E-05mmHg at 25°C
• Boiling Point: 340.2°C at 760 mmHg
• Flash Point: 148.4°C
• PSA: 59.32000
• Density: 1.2g/cm³
• LogP: 1.35348
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

99.3% ^*data from raw suppliers

Methyl2-Cyano-5-methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)C#N)C(=O)OC

Technology Process of Methyl 2-cyano-5-methoxybenzoate

There total 7 articles about Methyl 2-cyano-5-methoxybenzoate 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: 91.0%

methyl 2-bromo-5-methoxybenzoate (35450-36-3) + copper(I) cyanide (544-92-3) + potassium cyanide (151-50-8) → 2-cyano-5-methoxybenzoic acid methyl ester (127510-95-6)

Guidance literature:

methyl 2-bromo-5-methoxybenzoate; copper(I) cyanide; In N,N-dimethyl-formamide; at 140 ℃; for 0.5h;

potassium cyanide; In water; at 50 ℃; for 1h; Product distribution / selectivity;

Reference yield: 72.4%

potassium hexacyanoperferrate + methyl 2-bromo-5-methoxybenzoate (35450-36-3) → 2-cyano-5-methoxybenzoic acid methyl ester (127510-95-6)

Guidance literature:

With sodium carbonate; palladium diacetate; In ISOPROPYLAMIDE; at 110 ℃; for 36h; Product distribution / selectivity;

Reference yield: 72.4%

methyl 2-bromo-5-methoxybenzoate (35450-36-3) + potassium ferrocyanide → 2-cyano-5-methoxybenzoic acid methyl ester (127510-95-6)

Guidance literature:

With palladium diacetate; sodium carbonate; In ISOPROPYLAMIDE; at 110 ℃; for 36h; Inert atmosphere;

DOI:10.1016/j.tetlet.2008.12.099

upstream raw materials:

methyl 2-bromo-5-methoxybenzoate

dicyanozinc

copper(I) cyanide

potassium cyanide

Downstream raw materials:

3-imino-6-methoxy-isoindolin-1-one

2-aminomethyl-5-methoxy-benzoic acid methyl ester

2-aminomethyl-5-methoxybenzoic acid methyl ester hydrochloride

5'-methoxy-spiro[cyclopropane-11'-isoindol]-3'(2'H)-one

Refernces

• 1、 Zheng, Shuyan,Yu, Chunhui,Shen, Zhengwu. "Ethyl cyanoacetate: A new cyanating agent for the palladium-catalyzed cyanation of aryl halides". supporting information; experimental part. p. 3644 - 3647. Retrieved 2012/08/28.
• 2、 -. "ISOINDOLE DERIVATIVES". Page/Page column 26-27. . Retrieved 2010/11/30.