2-Amino-6-methoxybenzoic acid

Base Information

• Chemical Name: 2-Amino-6-methoxybenzoic acid
• CAS No.: 53600-33-2
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.164
• Hs Code.: 29225090
• European Community (EC) Number: 671-443-0
• DSSTox Substance ID: DTXSID90370688
• Nikkaji Number: J1.755.644D
• Wikidata: Q72438659
• Mol file: 53600-33-2.mol

Synonyms:2-Amino-6-methoxybenzoic acid;53600-33-2;6-methoxyanthranilic acid;2-Amino-6-methoxybenzoicacid;6-Amino-o-anisic acid;Benzoic acid, 2-amino-6-methoxy-;MFCD01941328;2-amino-6-methoxy-benzoic Acid;6-Methoxy-anthranilic acid;2-amino-6methoxybenzoic acid;SCHEMBL284305;2-amino-6-methoxy-benzoicacid;2-amino-6-methoxylbenzoic acid;2-amino-6-methoxy benzoic acid;DTXSID90370688;DYZDIWNRWSNVPT-UHFFFAOYSA-N;2-amino-6-(methyloxy)benzoic acid;AKOS006229576;AC-2644;CS-W002870;PS-4607;SY002376;2-Amino-6-methoxybenzoic acid, AldrichCPR;A7799;AM20040658;FT-0649947;EN300-83930;J-508000;Z1201621530

Chemical Property of 2-Amino-6-methoxybenzoic acid

Chemical Property:

• Vapor Pressure: 3.08E-05mmHg at 25°C
• Melting Point: >85 (dec.)
• Refractive Index: 1.603
• Boiling Point: 341.5 °C at 760mmHg
• PKA: 4.83±0.10(Predicted)
• Flash Point: 160.4 °C
• PSA: 72.55000
• Density: 1.303 g/cm³
• LogP: 1.55680
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.6
• 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-6-methoxybenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1C(=O)O)N
• Uses: 2-Amino-6-methoxybenzoic acid is a reagent is the synthesis of Tasquinimod (T007820). Tasquinimod is an orally active antiangiogenic agent which may inhibit HDAC4 signalling. This affects cancer cell survival thus making this compound and anti-cancer agent.

Technology Process of 2-Amino-6-methoxybenzoic acid

There total 21 articles about 2-Amino-6-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: 100.0%

2-nitro-6-methoxybenzoic acid (53967-73-0) → 6-methoxyanthranilic acid (53600-33-2)

Guidance literature:

palladium; In ethanol;

Reference yield:

2,6-dinitrobenzoic acid (603-12-3) → 6-methoxyanthranilic acid (53600-33-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / sodium hydrogen carbonate / acetone / 30 h / Heating

2: 73 percent / ethanol / 11 h / Heating

3: 16 g / H₂ / 10percent Pd/C / methanol / 760 Torr

4: 5percent NaOH

With sodium hydroxide; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; ethanol; acetone;

Reference yield:

2-amino-6-methoxybenzonitrile (1591-37-3) → 6-methoxyanthranilic acid (53600-33-2)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja00453a036

upstream raw materials:

2-nitro-6-methoxybenzoic acid

N-(tert-butoxycarbonyl)-6-methoxyanthranilic acid

ethyl 2-(N-ethoxycarbonyl-N-pivaloyl)amino-6-methoxybenzoate

2-amino-6-methoxybenzonitrile

Downstream raw materials:

S-<2-Carboxy-3-methoxy-phenyl>-thioglykolsaeure

2-bromo-6-methoxybenzoic acid

2-(6-Bromo-3-methyl-indazol-1-yl)-6-methoxy-benzoic acid

6-amino-1-(2-carboxy-3-methoxyphenyl)-3-methylindazole

Refernces

• 1、 Sugaya,Mimura,Kato,Ikuta,Mimura,Kasai,Tomioka. "Synthesis of a 6H-pyrazolo[4,5,1-de]acridin-6-one derivative: A useful intermediate of antitumour agents". . p. 73 - 76. Retrieved 2007/10/02.
• 2、 -. "4H-3,1-BENZOXAZIN-4-ONES AND RELATED COMPOUNDS AND USE AS ENZYME INHIBITORS". . . Retrieved 2008/06/13.