2-Amino-5-cyanobenzoic acid

Base Information

• Chemical Name: 2-Amino-5-cyanobenzoic acid
• CAS No.: 99767-45-0
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00434821
• Nikkaji Number: J612.093H
• Wikidata: Q82249350
• Mol file: 99767-45-0.mol

Synonyms:2-Amino-5-cyanobenzoic acid;99767-45-0;Benzoic acid, 2-amino-5-cyano-;MFCD20485816;2-Amino-5-cyanobenzoicacid;SCHEMBL634467;DTXSID00434821;HQNZNIJPAYTWJK-UHFFFAOYSA-N;CL9197;AKOS016001712;CS-W005229;DS-3636;SB76085;SY253699;EN300-151690;Z1262514273

Chemical Property of 2-Amino-5-cyanobenzoic acid

Chemical Property:

• Boiling Point: 389.3±37.0 °C(Predicted)
• PKA: 4.38±0.10(Predicted)
• PSA: 87.11000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 1.41988
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 231

Purity/Quality:

98%Min ^*data from raw suppliers

2-amino-5-cyanobenzoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Amino-5-cyanobenzoic acid

There total 6 articles about 2-Amino-5-cyanobenzoic acid 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: 97.5%

methyl 2-AMINO-5-CYANOBENZOATE (159847-81-1) → 2-amino-5-cyanobenzoic acid (99767-45-0)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 27.5h;

Reference yield: 57.0%

copper(l) cyanide + 5-Bromo-2-aminobenzoic acid (5794-88-7) → 2-amino-5-cyanobenzoic acid (99767-45-0)

Guidance literature:

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

Reference yield:

4-amino-3-iodobenzonitrile (33348-34-4) → 2-amino-5-cyanobenzoic acid (99767-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine / acetonitrile / 60 °C / Inert atmosphere

2: lithium hydroxide; water / tetrahydrofuran / 3 h / 20 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; water; palladium diacetate; potassium carbonate; triethylamine; lithium hydroxide; In tetrahydrofuran; acetonitrile;

upstream raw materials:

2,4-dicyanoaniline

2,4-dibromo-aniline

methyl 2-AMINO-5-CYANOBENZOATE

5-Bromo-2-aminobenzoic acid

Downstream raw materials:

10-[(3-chloro-4-methoxybenzyl)amino]-2-methyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile

tert-butyl 10-((3-chloro-4-methoxybenzyl)amino)-8-cyano-3,4-dihydrobenzo[b][1,6]naphthyridine-2-(1H)-carboxylate

10-((3-chloro-4-methoxybenzyl)amino)-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile

2-acetyl-10-[(3-chloro-4-methoxybenzyl)amino]-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile

Refernces

• 1、 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.
• 2、 -. "6-SUBSTITUTED QUINAZOLINONE INHIBITORS". Paragraph 0140. . Retrieved 2014/07/07.