2-Amino-5-methoxybenzoic acid

Base Information

• Chemical Name: 2-Amino-5-methoxybenzoic acid
• CAS No.: 6705-03-9
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.164
• Hs Code.: 29225090
• European Community (EC) Number: 628-679-4
• NSC Number: 126996
• DSSTox Substance ID: DTXSID50298930
• Nikkaji Number: J1.555.626I
• Wikidata: Q72438652
• Mol file: 6705-03-9.mol

Synonyms:5-methoxyanthranilic acid

Chemical Property of 2-Amino-5-methoxybenzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00101mmHg at 25°C
• Melting Point: 148-152 °C
• Refractive Index: 1.569
• Boiling Point: 349.9 °C at 760 mmHg
• PKA: 2.08±0.10(Predicted)
• Flash Point: 165.4 °C
• PSA: 72.55000
• Density: 1.303 g/cm³
• LogP: 1.55680
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Methanol (Slightly)
• XLogP3: 0.9
• 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% ^*data from raw suppliers

2-Amino-5-methoxybenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)N)C(=O)O
• Uses: 2-Amino-5-methoxybenzoic Acid is used in the synthesis of quinazolinone class of histamine H3 receptor inverse agonists. It is also used in the synthesis of Alogliptin, a selective inhibitor of the s erine protease dipeptidyl peptidase IV. 2-Amino-5-methoxybenzoic acid is a general reagent used in the synthesis of substituted isoquinolinonaphthyridines, quinazolinones, imidazobenzodiazepines, pyridoquinazolones and polycyclic hexahydrobenzo[c]acridines.

Technology Process of 2-Amino-5-methoxybenzoic acid

There total 28 articles about 2-Amino-5-methoxybenzoic 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: 99.0%

methyl 2-amino-5-methoxybenzoate (2475-80-1) → 2-Amino-5-methoxybenzoic acid (6705-03-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃;

DOI:10.1016/j.ejmech.2020.112857

Reference yield: 96.0%

5-methoxylindole (1006-94-6) → 2-Amino-5-methoxybenzoic acid (6705-03-9)

Guidance literature:

5-methoxylindole; With bromamine B; sodium hydroxide; palladium dichloride; In water; acetonitrile; at 60 ℃; for 3.33333h; pH=12;

In water; Acidic conditions;

DOI:10.1080/00397910903457274

Reference yield: 96.0%

5,5′-dimethoxyindigo (100174-55-8) → 2-Amino-5-methoxybenzoic acid (6705-03-9)

Guidance literature:

5,5′-dimethoxyindigo; With bromamine B; sodium hydroxide; palladium dichloride; In water; acetonitrile; at 60 ℃; for 2.16667h; pH=12;

In water; Acidic conditions;

DOI:10.1080/00397910903457274

upstream raw materials:

5-methoxy-2-nitro-benzoic acid

2-hydroxyimino-N-(4-methoxyphenyl)acetamide

6-methoxy-3-(4-methoxy-phenyl)-1H-quinazoline-2,4-dione

2-amino-5-methoxybenzamide

Downstream raw materials:

7-methoxy-3-p-tolyl-thiazolo[2,3-b]quinazolin-5-one

2-methyl-6-(methoxy)-3,1-benzoxazin-4-one

6-Methoxyquinazolin-4-one

7-methoxy-1-phenyl-thiazolo[3,2-a]quinazolin-5-one

Refernces

• 1、 Yao, Hong,Uras, Giuseppe,Zhang, Pengfei,Xu, Shengtao,Yin, Ying,Liu, Jie,Qin, Shuai,Li, Xinuo,Allen, Stephanie,Bai, Renren,Gong, Qi,Zhang, Haiyan,Zhu, Zheying,Xu, Jinyi. "Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease". . p. 7483 - 7506. Retrieved 2021/06/28.
• 2、 Han, Sheng,Sang, Yali,Wu, Yan,Tao, Yuan,Pannecouque, Christophe,De Clercq, Erik,Zhuang, Chunlin,Chen, Fen-Er. "Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles". . . Retrieved 2019/11/11.