92-70-6

Basic information

• Product Name: 3-Hydroxy-2-naphthoic acid
• Synonyms: 3-hydroxy-2-naphthoicaci;3-Hydroxy-beta-naphthoic acid;3-hydroxy-beta-naphthoicacid;3-Hydroxynaphthalenecarboxylic acid-(2);3-Naphthol-2-carboxylic acid;3-naphthol-2-carboxylicacid;beta-naphthoicacid,3-hydroxy;BONA
• CAS NO: 92-70-6
• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.18
• EINECS: 202-180-8
• Product Categories: Intermediates of Dyes and Pigments;Intermediates;Naphthalene derivatives;Organics;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 92-70-6.mol

Chemical Properties

• Melting Point: 218-221 °C(lit.)
• Boiling Point: 283.17°C (rough estimate)
• Flash Point: >150°C
• Appearance: Yellow to beige-brown/Fine Crystalline Powder
• Density: 1.43 g/cm3 (23℃)
• Vapor Pressure: 4.68E-06mmHg at 25°C
• Refractive Index: 1.7160 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 0.072g/l practically insoluble
• PKA: 3.02±0.30(Predicted)
• Water Solubility: PRACTICALLY INSOLUBLE
• Merck: 14,4835
• BRN: 744100
• CAS DataBase Reference: 3-Hydroxy-2-naphthoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-2-naphthoic acid(92-70-6)
• EPA Substance Registry System: 3-Hydroxy-2-naphthoic acid(92-70-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 1
• RTECS: QL1755000
• TSCA: Yes
• Hazardous Substances Data: 92-70-6(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Industry:
3-Hydroxy-2-naphthoic acid is used as an intermediate for the production of dyes and pigments, contributing to their color stability and resistance to various environmental factors.
Used in Insecticide Production:
3-Hydroxy-2-naphthoic acid serves as an intermediate in the synthesis of insecticides, playing a crucial role in the development of effective pest control agents.
Used in Pharmaceutical Industry:
3-Hydroxy-2-naphthoic acid is utilized as an intermediate in the production of pharmaceuticals, aiding in the creation of various medicinal compounds.
Used in Coupling with Diazo Compounds:
2-hydroxy-3-naphthoic acid (BON) is coupled with diazo compounds, and their calcium salts produce bright red bleed resistance pigments. The manganese salt, although more expensive, offers better exterior durability compared to calcium or barium salts. The BON red pigments are characterized by their exceptional color stability, resistance to acids and alkalies, and non-toxic properties.

Purification Methods

Crystallise it from water or acetic acid. The S-benzyisothiuronium salt has m 216-217o (from EtOH). It forms many metal complex salts. [Beilstein 10 H 333, 10 III 1084.]

InChI:InChI=1/C11H8O3/c12-10-6-8-4-2-1-3-7(8)5-9(10)11(13)14/h1-6,12H,(H,13,14)/p-1

Upstream product

• 92024-90-3 benz[d]oxepin-2,4-dicarboxylic acid 
• 871874-72-5 2-hydroxy-3-phenylcarbamoyl-naphthalene-1-sulfonic acid 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 135-19-3 β-naphthol 
• 71-43-2 benzene 
• 15719-64-9 methylammonium carbonate 
• 124-38-9 carbon dioxide 
• 875-83-2 sodium 2-naphtholate 
• 56-93-9 benzyltrimethylammonium chloride 
• 1310-58-3 potassium hydroxide 
• 54914-85-1 1,2-di(3-methylphenoxy)ethane 
• 104-66-5 1,2-diphenoxyethane 
• 93-09-4 naphthalene-2-carboxylate 

Downstream Products

• 84837-23-0 3-hydroxy-[2]naphthoic acid-(1⁽²⁾H-indazol-6-ylamide) 
• 5464-07-3 3-acetoxy-2-naphthoic acid 
• 93-45-8 N-(4-hydroxyphenyl)-2-naphthylamine 
• 30366-97-3 3-hydroxy-[2]naphthoic acid-(3-acetyl-anilide) 
• 132-68-3 naphthol ASBO 
• 450-33-9 3-hydroxy-N-(3-trifluromethylphenyl)naphthalene-2-carboxamide 
• 3651-62-5 3-hydroxy-N-(4-methylphenyl)naphthalene-2-carboxamide 
• 644-16-6 N-(p-tolyl)naphthalen-2-amine 
• 92-78-4 naphthol AS-E 
• 92-77-3 2,3-oxynaphthoic acid phenylamide 
• 130-85-8 Pamoic acid 
• 94984-33-5 m-tolyl 3-hydroxy-2-naphthoate 
• 2208-20-0 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide 
• 70083-12-4 3-hydroxy-N-(2-nitrophenyl)naphthalene-2-carboxamide 

Relevant articles and documents

Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids

A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.

Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade

A palladium-catalyzed intramolecular α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols is reported. With ortho-bromobenzyl-substituted α-fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. (Figure presented.).

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system

A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.

A solvent method for producing continuous carbonization 2-naphthol, cogeneration 2,3 acid method and device (by machine translation)

The invention discloses a method for producing continuous carbonization solvent the 2 [...] naphthol, cogeneration 2,3 acid method and device. Method is to adopt continuous carbonization and 2,3 the new process [...] acid, has changed the traditional production process and method, to naphthalene series dye, pigment and derivatives an important intermediate for the production of new production technologies; the device of this invention includes 2 the system and outputs natphthol [...] the 2 [...] hydroxy -3 the output system [...] formic acid, 2 the system includes extracting [...] natphthol chromophore outputs, mixer, and the rectifying tower A, carbonization reaction kettle, 2 the crude distillation tower [...] naphthol, 2 the finished natphthol [...] the rectifying tower and the slice-packaging device, the 2 [...] hydroxy -3 the formic acid [...] output system includes a stationary separation system, and filter-pressing apparatus, dyeworks acidified system, centrifugal-washing and drying-packing device, extraction chromophore mixer connected in sequence, and the rectifying tower A, carbonization reaction kettle, 2 the crude distillation tower [...] naphthol, 2 the product natphthol [...] the rectifying tower and the slice-packing device, 2 the bottom material distillation tower tower[...] naphthol crude product (2,3 the acid [...] double-sodium salt) are connected in sequence still separation system, and filter-pressing apparatus, dyeworks acidified system, centrifuge and dry packing device. (by machine translation)

A versatile approach for the synthesis of para -substituted arenes via palladium-catalyzed C-H functionalization and protodecarboxylation of benzoic acids

While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.

Production of aromatic hydroxycarboxylic acid

PROBLEM TO BE SOLVED: To provide an environment-friendly method for producing aromatic hydroxycarboxylic acid in high yield even under low temperature reaction conditions. SOLUTION: The method for producing aromatic hydroxycarboxylic acid includes a process of reacting an alkali metal salt of an aromatic hydroxy compound with carbon dioxide in a medium, where the reaction is performed in the presence of 0.01-1.0 mole of one or more alcohol compounds and/or ether compounds for 1 mole of the alkali metal salt of the aromatic hydroxy compound. COPYRIGHT: (C)2013,JPOandINPIT

Production of aromatic hydroxycarboxylic acid

PROBLEM TO BE SOLVED: To provide a production method capable of obtaining aromatic hydroxycarboxylic acid at high yield even under a reaction condition at low temperature. SOLUTION: The method for production of aromatic hydroxycarboxylic acid includes a process of reacting an alkali metal salt of aromatic hydroxy compounds with carbon dioxide in a medium. The method is characterized by performing the above reaction in the presence of a ligand alone or as its metal complex of 0.01-1.0 mol based on 1 mol of the alkali metal salt of the aromatic hydroxy compound. COPYRIGHT: (C)2012,JPOandINPIT

General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.

PD(II)-CATALYZED HYDROXYLATION OF ARENES WITH O2 OR AIR

Pd (II) -catalyzed ortho-hydroxylat ion of variously substituted aromatic carboxylic acids under O2 or air is achieved under non-acidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.

Ni-catalyzed reduction of inert C-O bonds: A new strategy for using aryl ethers as easily removable directing groups

An efficient Ni-catalyzed protocol for the reductive cleavage of inert C-O bonds has been developed. The method is characterized by its simplicity and wide scope, thereby allowing the use of aryl ethers as easily removable directing groups in organic synthesis.