4-Hydroxy-1-naphthoic acid

Base Information

• Chemical Name: 4-Hydroxy-1-naphthoic acid
• CAS No.: 7474-97-7
• Molecular Formula: C11H8 O3
• Molecular Weight: 188.183
• Hs Code.: 2918290000
• NSC Number: 401125
• UNII: OO8UA94R91
• DSSTox Substance ID: DTXSID10322381
• Nikkaji Number: J167.276B
• Wikidata: Q82080923
• Mol file: 7474-97-7.mol

Synonyms:4-Hydroxy-1-naphthoic acid;7474-97-7;4-hydroxynaphthalene-1-carboxylic acid;1-Naphthalenecarboxylic acid, 4-hydroxy-;NSC-401125;1-hydroxy-4-naphthoic acid;OO8UA94R91;1-Hydroxy-4-naphthalenecarboxylic acid;NSC401125;p-hydroxynaphthoic acid;4-hydroxynaphthoic acid;4-hydroxy-1-naphthoicacid;UNII-OO8UA94R91;4-Naphthol-1-carboxylic acid;SCHEMBL678559;DTXSID10322381;AKOS006275716;AT25660;CS-0231152;FT-0705286;EN300-107268;Z1198150516

Chemical Property of 4-Hydroxy-1-naphthoic acid

Chemical Property:

• Vapor Pressure: 1.35E-08mmHg at 25°C
• Melting Point: 183-184 °C
• Boiling Point: 442.2°Cat760mmHg
• PKA: 4.34±0.10(Predicted)
• Flash Point: 235.4°C
• PSA: 57.53000
• Density: 1.399g/cm³
• LogP: 2.24360
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 188.047344113
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxynaphthalene-1-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=C2O)C(=O)O

Technology Process of 4-Hydroxy-1-naphthoic acid

There total 3 articles about 4-Hydroxy-1-naphthoic 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: 22.0%

1-naphthalenecarboxylic acid (86-55-5) → 4-hydroxy-1-naphthoic acid (7474-97-7) + 5-hydroxy-1-naphthoic acid (2437-16-3)

Guidance literature:

With Streptomyces lividans expressing pIJ₆₀₂₁-bphA₁⁽²⁰⁷²⁾A₂A₃A₄; at 30 ℃; for 24h; Microbiological reaction;

DOI:10.1016/S0040-4020(03)00180-7

Reference yield: 6.0%

formic acid (64-18-6) + naphthalene (91-20-3,71998-51-1,72931-45-4) → 4-hydroxy-1-naphthoic acid (7474-97-7) + 5-hydroxy-1-naphthoic acid (2437-16-3)

Guidance literature:

With dipotassium peroxodisulfate; trifluoroacetic acid; palladium(II) trifluoroacetate; In dichloromethane; at 40 ℃;

DOI:10.1021/ol049166l

Reference yield:

α-naphthol (90-15-3) + carbon dioxide (124-38-9,18923-20-1) → 4-hydroxy-1-naphthoic acid (7474-97-7) + 1-hydroxy-2-naphthoic acid (86-48-6)

Guidance literature:

With 2,3,6,7-tetramethoxy-9(10H)-anthracenone; caesium carbonate; In dimethyl sulfoxide; at 25 ℃; for 18h; under 2280.15 Torr; Overall yield = 56 percent; regioselective reaction; Irradiation; Sealed tube;

DOI:10.1016/j.chempr.2020.08.022

upstream raw materials:

1-naphthalenecarboxylic acid

formic acid

naphthalene

α-naphthol

Downstream raw materials:

3-amino-4-hydroxy-[1]naphthoic acid

4-Carboxy-1,2-naphthochinon

4-(phenylamino)naphthalene-1,2-dione

4-Phenylazo-1-naphthol

Refernces

• 1、 Shibahara, Fumitoshi,Kinoshita, Shinsuke,Nozaki, Kyoko. "Palladium(II)-catalyzed sequential hydroxylation-carboxylation of biphenyl using formic acid as a carbonyl source". . p. 2437 - 2439. Retrieved 2007/10/03.