Methyl 2-amino-5-cyanobenzoate

Base Information

• Chemical Name: Methyl 2-amino-5-cyanobenzoate
• CAS No.: 159847-81-1
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50434836
• Wikidata: Q82249375
• Mol file: 159847-81-1.mol

Synonyms:METHYL 2-AMINO-5-CYANOBENZOATE;159847-81-1;Benzoic acid, 2-amino-5-cyano-, methyl ester;MFCD11041293;MAPO(R);SCHEMBL4842734;Methyl-2-amino-5-cyanobenzoate;DTXSID50434836;XVICOGIQWUAIAV-UHFFFAOYSA-N;AKOS006307311;2-amino-5-cyanobenzoic acid methyl ester;DS-12059;SY059276;2-amino-5-cyano-benzoic acid methyl ester;CS-0061809;FT-0727268;EN300-134670;A856802;Z1198305830

Chemical Property of Methyl 2-amino-5-cyanobenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 334.08oC at 760 mmHg
• PKA: 0.95±0.10(Predicted)
• Flash Point: 155.846oC
• PSA: 76.11000
• Density: 1.262g/cm3
• LogP: 1.50828
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-amino-5-cyanobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 2-amino-5-cyanobenzoate

There total 9 articles about Methyl 2-amino-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: 90.0%

copper(l) cyanide + 5-bromo-2-aminobenzoic acid methyl ester (52727-57-8) → methyl 2-AMINO-5-CYANOBENZOATE (159847-81-1)

Guidance literature:

In N,N-dimethyl-formamide; Reflux;

Reference yield: 85.0%

5-bromo-2-aminobenzoic acid methyl ester (52727-57-8) → methyl 2-AMINO-5-CYANOBENZOATE (159847-81-1)

Guidance literature:

With zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In DMF (N,N-dimethyl-formamide); at 90 - 100 ℃; for 8h;

Reference yield: 85.0%

copper(I) cyanide (544-92-3) + 5-bromo-2-aminobenzoic acid methyl ester (52727-57-8) → methyl 2-AMINO-5-CYANOBENZOATE (159847-81-1)

Guidance literature:

copper(I) cyanide; 5-bromo-2-aminobenzoic acid methyl ester; In 1-methyl-pyrrolidin-2-one; for 5h; Heating / reflux;

With hydrogenchloride; iron(III) chloride; In 1-methyl-pyrrolidin-2-one; water; at 60 ℃; for 1h;

upstream raw materials:

methanol

2,4-dicyanoaniline

2,4-dibromo-aniline

copper(I) cyanide

Downstream raw materials:

2-bromo-5-thiocarbamoyl-benzoic acid methyl ester

2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester

4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4'-dicarboxylic acid 4'-tert-butyl ester 2-methyl ester

4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4'-dicarboxylic acid 2-methyl ester

Refernces

• 1、 Caspers, Lucien D.,Spils, Julian,Damrath, Mattis,Lork, Enno,Nachtsheim, Boris J.. "One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts". . p. 9161 - 9178. Retrieved 2020/08/14.
• 2、 Fiorito, Jole,Vendome, Jeremie,Saeed, Faisal,Staniszewski, Agnieszka,Zhang, Hong,Yan, Shijun,Deng, Shi-Xian,Arancio, Ottavio,Landry, Donald W.. "Identification of a Novel 1,2,3,4-Tetrahydrobenzo[b][1,6]naphthyridine Analogue as a Potent Phosphodiesterase 5 Inhibitor with Improved Aqueous Solubility for the Treatment of Alzheimer's Disease". . p. 8858 - 8875. Retrieved 2017/11/14.