Methyl 2-amino-3-hydroxybenzoate

Base Information

• Chemical Name: Methyl 2-amino-3-hydroxybenzoate
• CAS No.: 17672-21-8
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.164
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID20170178
• Nikkaji Number: J60.476C
• Wikidata: Q72437708
• Mol file: 17672-21-8.mol

Synonyms:Methyl 2-amino-3-hydroxybenzoate;17672-21-8;Methyl 3-hydroxyanthranilate;benzoic acid, 2-amino-3-hydroxy-, methyl ester;2-Amino-3-hydroxy-benzoic acid methyl ester;Anthranilic acid, 3-hydroxy-, methyl ester;BRN 2830430;MFCD01675233;4-14-00-02072 (Beilstein Handbook Reference);Methyl2-Amino-3-hydroxybenzoate;2-amino-3-hydroxybenzoic acid methyl ester;SCHEMBL148358;DTXSID20170178;methyl-2-amino-3-hydroxybenzoate;o-Amino-m-oxybenzoesauremethylester;2-Amino-3-hydroxybenzoic acid methyl;AKOS006276482;CS-W022796;AC-23864;LS-20533;SY035780;AM20080605;EN300-250702;A812204;Z1198157520;methyl 2-amino-3-hydroxy-benzoate;Methyl 2-Amino-3-hydroxybenzoate

Chemical Property of Methyl 2-amino-3-hydroxybenzoate

Chemical Property:

• Vapor Pressure: 0.000348mmHg at 25°C
• Melting Point: 97-99℃
• Refractive Index: 1.5570 (estimate)
• Boiling Point: 309.6°Cat760mmHg
• Flash Point: 141°C
• PSA: 72.55000
• Density: 1.305g/cm³
• LogP: 1.34220
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 167.058243149
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

98%min ^*data from raw suppliers

Methyl3-Hydroxyanthranilate ^*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)O)N
• Uses: Methyl 3-Hydroxyanthranilate is an intermediate in the synthesis of metabolites of Bentazon (B120580), a selective post-emergence herbicide.

Technology Process of Methyl 2-amino-3-hydroxybenzoate

There total 22 articles about Methyl 2-amino-3-hydroxybenzoate 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: 99.0%

methyl 3-hydroxy-2-nitrobenzoate (89942-77-8) → 2-amino-3-hydroxy-benzoic acid methyl ester (17672-21-8)

Guidance literature:

With palladium on activated charcoal; hydrogen;

DOI:10.1039/c3ra41080c

Reference yield: 95.0%

2-amino-3-hydroxybenzoic acid hydrobromide (906096-11-5) + diazomethyl-trimethyl-silane (18107-18-1) → 2-amino-3-hydroxy-benzoic acid methyl ester (17672-21-8)

Guidance literature:

2-amino-3-hydroxybenzoic acid hydrobromide; diazomethyl-trimethyl-silane; In methanol; diethyl ether; toluene; at 0 ℃; for 0.333333h;

With acetic acid; In methanol; diethyl ether; toluene; at 0 - 20 ℃; for 0.5h;

Reference yield: 92.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3-hydroxyanthranilic acid (548-93-6) → 2-amino-3-hydroxy-benzoic acid methyl ester (17672-21-8)

Guidance literature:

In methanol; diethyl ether; at 0 ℃;

DOI:10.1016/j.bmc.2006.05.007

upstream raw materials:

methyl 3-hydroxy-2-nitrobenzoate

3-hydroxyanthranilic acid

diazomethane

methanol

Downstream raw materials:

2-phenylbenzo[d]oxazole-4-carboxylic acid

2-phenyl-benzooxazole-4-carboxylic acid (2-hydroxy-phenyl)-amide

3-hydroxy-2-[(2-phenyl-benzooxazole-4-carbonyl)-amino]-benzoic acid methyl ester

2-(2-benzyloxy-phenyl)-benzooxazole-4-carboxylic acid (2-hydroxy-phenyl)-amide

Refernces

• 1、 Radulovi?, Niko S.,Miltojevi?, Ana B.,Stojanovi?, Nikola M.,Randjelovi?, Pavle J.. "Distinct urinary metabolite profiles of two pharmacologically active N-methylanthranilates: Three approaches to xenobiotic metabolite identification". . p. 341 - 355. Retrieved 2017.
• 2、 Shibuya, Kimiyuki,Kawamine, Katsumi,Miura, Toru,Ozaki, Chiyoka,Edano, Toshiyuki,Mizuno, Ken,Yoshinaka, Yasunobu,Tsunenari, Yoshihiko. "Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors". . p. 4001 - 4013. Retrieved 2018/06/26.