2-Amino-4,6-dimethoxybenzoic acid

Base Information

• Chemical Name: 2-Amino-4,6-dimethoxybenzoic acid
• CAS No.: 21577-57-1
• Molecular Formula: C9H11NO4
• Molecular Weight: 197.191
• Hs Code.: 2922509090
• European Community (EC) Number: 838-627-4
• DSSTox Substance ID: DTXSID00470148
• Wikidata: Q72436137
• Mol file: 21577-57-1.mol

Synonyms:2-amino-4,6-dimethoxybenzoic acid;21577-57-1;2-amino-4,6-dimethoxy-benzoic Acid;2-Amino-4,6-dimethoxybenzoicacid;MFCD09031989;4,6-dimethoxyanthranilic acid;Benzoic acid, 2-amino-4,6-dimethoxy-;2-AMINO-4,6-DIMETHOXY-BENZOICACID;4,6-dimethoxy anthranilic acid;4,6-dimethoxy-anthranilic acid;SCHEMBL1012409;DTXSID00470148;HZBQKANLOSWJLU-UHFFFAOYSA-N;BCP19408;CS-B0786;AKOS008140039;AC-8531;AM84758;GS-4451;SB35426;SY029995;A4637;FT-0647615;EN300-74935;2-amino-4,6-dimethoxy-benzoic acid, AldrichCPR;J-507826

Chemical Property of 2-Amino-4,6-dimethoxybenzoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 120-125 °C
• Refractive Index: 1.582
• Boiling Point: 374.809 °C at 760 mmHg
• PKA: 5.10±0.10(Predicted)
• Flash Point: 180.478 °C
• PSA: 81.78000
• Density: 1.295 g/cm³
• LogP: 1.56540
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 197.06880783
• Heavy Atom Count: 14
• Complexity: 209

Purity/Quality:

98% ^*data from raw suppliers

2-Amino-4,6-dimethoxybenzoicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)OC)C(=O)O)N
• Uses: 2-Amino-4,6-dimethoxybenzoic Acid is used to prepare N-(5-Chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5- (tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine as a highly selective, orally available, dual-specific c-Src/Abl kinase inhibitor.

Technology Process of 2-Amino-4,6-dimethoxybenzoic acid

There total 5 articles about 2-Amino-4,6-dimethoxybenzoic 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: 59.0%

4,6-dimethoxyindoline-2,3-dione (21544-81-0) → 2-amino-4,6-dimethoxybenzoic acid (21577-57-1)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In water; at 100 ℃;

DOI:10.1002/chem.201002205

Reference yield:

2-nitro-4,6-dimethoxybenzoic acid (890093-49-9) → 2-amino-4,6-dimethoxybenzoic acid (21577-57-1)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; N,N-dimethyl-formamide; at 20 ℃; for 24h; under 262.526 Torr;

Reference yield:

3,5-dimethoxyaniline hydrochloride (40891-33-6) → 2-amino-4,6-dimethoxybenzoic acid (21577-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 0.5 h / 165 °C

2: 50 percent / NaOH; aq. H₂O₂ / 0.17 h / 100 °C

With sodium hydroxide; dihydrogen peroxide;

DOI:10.1021/jm0509389

upstream raw materials:

4,6-dimethoxyindoline-2,3-dione

3,5-dimethoxyaniline hydrochloride

2-nitro-4,6-dimethoxybenzoic acid

3.5-dimethoxyaniline

Downstream raw materials:

1,2-dihydro-5,7-dimethoxy-3,1-benzoxazine-2,4-dione

5,7-dimethoxy-2-methyl-3,1-benzoxazine-4-one

5,7-dimethoxy-3,1-benzoxazine-4-one

5,7-dimethoxy-2-isopropyl-3,1-benzoxazine-4-one

Refernces

• 1、 Shao, Mingfeng,He, Linhong,Zheng, Li,Huang, Lingxiao,Zhou, Yuanyuan,Wang, Taijing,Chen, Yong,Shen, Mingsheng,Wang, Fang,Yang, Zhuang,Chen, Lijuan. "Structure-based design, synthesis and in vitro antiproliferative effects studies of novel dual BRD4/HDAC inhibitors". supporting information. p. 4051 - 4055. Retrieved 2017/08/22.
• 2、 Zhang, Ai Hua,Jiang, Nan,Gu, Wen,Ma, Jing,Wang, Yu Rong,Song, Yong Chun,Tan, Ren Xiang. "Characterization, synthesis and self-aggregation of (-)-alternarlactam: A new fungal cytotoxin with cyclopentenone and isoquinolinone scaffolds". experimental part. p. 14479 - 14485. Retrieved 2011/03/21.