5-(Benzoylamino)-2-hydroxybenzoic acid

Base Information

• Chemical Name: 5-(Benzoylamino)-2-hydroxybenzoic acid
• CAS No.: 28772-37-4
• Molecular Formula: C₁₄H₁₁NO₄
• Molecular Weight: 257.246
• NSC Number: 159689
• UNII: N59FQM30D8
• DSSTox Substance ID: DTXSID60182952
• Wikidata: Q83053685
• Mol file: 28772-37-4.mol

Synonyms:5-(Benzoylamino)-2-hydroxybenzoic acid;28772-37-4;N59FQM30D8;NSC159689;NSC 159689;UNII-N59FQM30D8;NSC-159689;Oprea1_252496;SCHEMBL1129948;DTXSID60182952;5-benzamido-2-hydroxy-benzoic acid;STK729614;SALICYLIC ACID, 5-BENZAMIDO-;5-(BENZOYLAMINO)SALICYLIC ACID;AKOS000104567;Benzoic acid, 5-(benzoylamino)-2-hydroxy-;5-BENZOYLAMINO-2-HYDROXY-BENZOIC ACID;2-hydroxy-5-[(phenylcarbonyl)amino]benzoic acid;SR-01000507661;SR-01000507661-1

Chemical Property of 5-(Benzoylamino)-2-hydroxybenzoic acid

Chemical Property:

• Vapor Pressure: 1.67E-06mmHg at 25°C
• Boiling Point: 381.6°C at 760 mmHg
• Flash Point: 184.6°C
• Density: 1.434g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 257.06880783
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=CC(=C(C=C2)O)C(=O)O

Technology Process of 5-(Benzoylamino)-2-hydroxybenzoic acid

There total 3 articles about 5-(Benzoylamino)-2-hydroxybenzoic 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:

C16H15NO4 → 5-benzamido-2-hydroxybenzoic acid (28772-37-4)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; Inert atmosphere;

DOI:10.1002/ddr.21557

Reference yield:

5-Aminosalicylic Acid (89-57-6) → 5-benzamido-2-hydroxybenzoic acid (28772-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 8.5 h / Reflux; Inert atmosphere

2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3: lithium hydroxide monohydrate / tetrahydrofuran; methanol / Inert atmosphere

With lithium hydroxide monohydrate; sulfuric acid; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/ddr.21557

Reference yield:

ethyl 5-amino-2-hydroxybenzoate (62773-65-3) → 5-benzamido-2-hydroxybenzoic acid (28772-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: lithium hydroxide monohydrate / tetrahydrofuran; methanol / Inert atmosphere

With lithium hydroxide monohydrate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/ddr.21557

upstream raw materials:

5-Aminosalicylic Acid

ethyl 5-amino-2-hydroxybenzoate