5-Hydroxyanthranilic acid

Base Information

• Chemical Name: 5-Hydroxyanthranilic acid
• CAS No.: 394-31-0
• Molecular Formula: C7H7NO3
• Molecular Weight: 153.137
• Hs Code.: 29225090
• European Community (EC) Number: 628-812-6
• UNII: UF9WW3I410
• DSSTox Substance ID: DTXSID70192587
• Nikkaji Number: J71.710J
• Wikidata: Q27291057
• Mol file: 394-31-0.mol

Synonyms:Anthranilicacid, 5-hydroxy- (8CI);2-Amino-5-hydroxybenzoic acid;Benzoic acid, 2-amino-5-hydroxy-;Diabeton;Glyklaside;

Chemical Property of 5-Hydroxyanthranilic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 9.97E-08mmHg at 25°C
• Melting Point: 247 °C (dec.)(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 417.8 °C at 760 mmHg
• PKA: 2.08±0.10(Predicted)
• Flash Point: 206.5 °C
• PSA: 83.55000
• Density: 1.491 g/cm³
• LogP: 1.25380
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: Insoluble
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxyanthranilic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1O)C(=O)O)N
• Uses: An oral anti-diabetic drug.

Technology Process of 5-Hydroxyanthranilic acid

There total 23 articles about 5-Hydroxyanthranilic 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: 96.0%

indol-5-ol (1953-54-4) → 2-amino-5-hydroxybenzoic acid (394-31-0)

Guidance literature:

indol-5-ol; 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: 95.0%

C16H10N2O4 (340699-08-3) → 2-amino-5-hydroxybenzoic acid (394-31-0)

Guidance literature:

C₁₆H₁₀N₂O₄; 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

Reference yield:

2-hydroxylaminobenzoic acid (579-73-7) → 2-amino-5-hydroxybenzoic acid (394-31-0) + 2,2'-azoxy-di-benzoic acid (573-79-5)

Guidance literature:

With water; acetic acid;

upstream raw materials:

ortho-nitrobenzoic acid

5-hydroxy-2-nitrobenzoic acid

2-hydroxylaminobenzoic acid

2-(4-hydroxyphenylazo)benzoic acid

Downstream raw materials:

4-Butyl-benzoic acid 2-(4-butyl-phenyl)-4-oxo-4H-benzo[d][1,3]oxazin-6-yl ester

(E)-5-hydroxy-2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid

6-hydroxy-1,2-dihydro-4H-3,1-benzoxazin-2,4-dione

benzyl 5-(benzyloxy)-2-((ethoxycarbonyl)amino)benzoate

Refernces

• 1、 Ma, Hengchang,Li, Wenfeng,Wang, Jian,Xiao, Guanghai,Gong, Yuan,Qi, Chunxuan,Feng, Yunpeng,Li, Xiufang,Bao, Zhikang,Cao, Wei,Sun, Qiangsheng,Veaceslav, Caraus,Wang, Feng,Lei, Ziqiang. "Organocatalytic oxidative dehydrogenation of aromatic amines for the preparation of azobenzenes under mild conditions". scheme or table. p. 8358 - 8366. Retrieved 2012/09/21.
• 2、 Kumar, C. Vinod,Shivananda,Raju, C. Nagu,Jagadeesh. "Bromamine-B/PdCl2 is an efficient system for the synthesis of anthranilic acids from indoles and indigos". experimental part. p. 3480 - 3487. Retrieved 2011/02/22.