3-Hydroxy-2-naphthoic acid

Base Information

• Chemical Name: 3-Hydroxy-2-naphthoic acid
• CAS No.: 92-70-6
• Deprecated CAS: 12235-60-8,12235-61-9,12235-61-9
• Molecular Formula: C11H8O3
• Molecular Weight: 188.183
• Hs Code.: H6OHCOOH MOL WT. 188.18
• European Community (EC) Number: 202-180-8
• ICSC Number: 1759
• NSC Number: 3719
• UNII: C7S9D784HX
• DSSTox Substance ID: DTXSID3026560
• Nikkaji Number: J4.659K
• Wikipedia: 3-Hydroxy-2-naphthoic_acid
• Wikidata: Q27149406
• ChEMBL ID: CHEMBL229301
• Mol file: 92-70-6.mol

Synonyms:3-hydroxy-2-naphthoic acid;3-hydroxy-2-naphthoic acid, magnesium salt;3-hydroxy-2-naphthoic acid, potassium salt;3-hydroxy-2-naphthoic acid, sodium salt;BON acid;Regacholyl

Chemical Property of 3-Hydroxy-2-naphthoic acid

Chemical Property:

• Appearance/Colour: yellow to beige-brown fine crystalline powder
• Vapor Pressure: 4.68E-06mmHg at 25°C
• Melting Point: 218-221 °C(lit.)
• Refractive Index: 1.7160 (estimate)
• Boiling Point: 367.7 °C at 760 mmHg
• PKA: 3.02±0.30(Predicted)
• Flash Point: 190.4 °C
• PSA: 57.53000
• Density: 1.399 g/cm³
• LogP: 2.24360
• Storage Temp.: Store below +30°C.
• Solubility.: 0.072g/l practically insoluble
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 2.9
• 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

3-Hydroxy-2-naphthoic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Naphthoic Acids
• Canonical SMILES: C1=CC=C2C=C(C(=CC2=C1)C(=O)O)O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the kidneys, liver and endocrine system.
• Uses: 3-Hydroxy-2-naphthoic acid is mainly used as intermediate for the production of dyes and pigments. Further uses are as intermediate for insecticides and pharmaceuticals (ECB, 2000). 2-hydroxy-3-naphthoic acid (BON) is coupled with diazo compounds and their calcium salts are bright red bleed resistance pigments. The somewhat higher cost manganese salt shows better exterior durability than the calcium or barium salts. The BON red pigments are characterized by an extremely high degree of color stability, resistance to acids and alkalies and are nontoxic.

Technology Process of 3-Hydroxy-2-naphthoic acid

There total 70 articles about 3-Hydroxy-2-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: 4.7%

carbon dioxide (124-38-9,18923-20-1) + potassium 2-naphthoxide (36294-21-0) → 6-Hydroxy-2-naphthoic acid (16712-64-4) + 3-Hydroxy-2-naphthoic acid (92-70-6)

Guidance literature:

With 2,3-dimethyl-2,3-butane diol; at 210 ℃; for 4h; under 2250.23 Torr; Autoclave;

Reference yield:

3-hydroxy-4-(α-hydroxy-benzyl)-[2]naphthoic acid methyl ester (871901-32-5) → benzaldehyde (100-52-7) + 3-Hydroxy-2-naphthoic acid (92-70-6)

Guidance literature:

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + 3-hydroxy-4-(α-hydroxy-benzyl)-[2]naphthoic acid methyl ester (871901-32-5) → benzaldehyde (100-52-7) + 3-Hydroxy-2-naphthoic acid (92-70-6)

Guidance literature:

upstream raw materials:

benz[d]oxepin-2,4-dicarboxylic acid

2-hydroxy-3-phenylcarbamoyl-naphthalene-1-sulfonic acid

sodium 3-hydroxy-4-sulphonato-2-naphthoic acid

potassium 2-naphthoxide

Downstream raw materials:

3-hydroxy-[2]naphthoic acid-(2-methoxy-dibenzofuran-3-ylamide)

3-acetoxy-2-naphthoic acid

3-hydroxy-[2]naphthoic acid-(3-acetyl-anilide)

3-hydroxy-N-(4-methylphenyl)naphthalene-2-carboxamide

Refernces

• 1、 Luo, Feihua,He, Shuhua,Gou, Quan,Chen, Jinyang,Zhang, mingzhong. "Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids". . . Retrieved 2021/10/06.
• 2、 Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.. "Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system". . p. 17806 - 17812. Retrieved 2018/05/28.