83-55-6

Basic information

• Product Name: 5-Amino-1-naphthol
• Synonyms: 1-Naphthalenol, 5-amino-;1-Naphthol, 5-amino-;5-amino-1-naphthaleno;5-Amino-alpha-naphthol;C.I. 76650;5-AMINO-1-NAPHTHOL;5-HYDROXY-1-NAPHTHYLAMINE;1-AMINO-5-HYDROXYNAPHTHALENE
• CAS NO: 83-55-6
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 201-486-9
• Product Categories: Intermediates of Dyes and Pigments;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 83-55-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 190 °C (dec.)(lit.)
• Boiling Point: 284.68°C (rough estimate)
• Flash Point: 182.6 °C
• Appearance: pale purple to brown-purple crystalline powder
• Density: 1.1202 (rough estimate)
• Vapor Pressure: 2.92E-06mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.97(at 25℃)
• CAS DataBase Reference: 5-Amino-1-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-1-naphthol(83-55-6)
• EPA Substance Registry System: 5-Amino-1-naphthol(83-55-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 83-55-6(Hazardous Substances Data)

Usage

Chemical Properties

pale purple to brown-purple crystalline powder

Uses

5-Amino-1-naphthol is used as a coupling component for azo dyes (coupling takes place ortho to the amino or hydroxyl group, or para to the hydroxyl group depending on the pH), and as an intermediate for sulfur dyes.

Preparation

1-Aminonaphthalene-5-sulfonic acid paste (Section 6.2) is added to molten sodium hydroxide at 200°C, and the reaction is completed by heating slowly to 250°C and maintaining this temperature for 3 h. After dilution and careful neutralization with hydrochloric acid, 5-amino-1-naphthol precipitates in 85 % yield (mp 192°C).

InChI:InChI=1/C10H9NO.ClH/c11-9-5-1-4-8-7(9)3-2-6-10(8)12;/h1-6,12H,11H2;1H

Upstream product

• 2243-62-1 1,5-naphthalenediamine 
• 91-20-3 naphthalene 
• 117-59-9 1-hydroxynaphthalene-5-sulphonic acid 
• 84-89-9 1-aminonaphthalene-5-sulfonic acid 
• 51114-73-9 5-nitro-1-tetralone 
• 51642-27-4 5-azidonaphthalen-1-ol 
• 121-69-7 N,N-dimethyl-aniline 
• 6304-46-7 5-nitro-1-naphthol 
• 130-13-2 sodium 4-amino-1-naphthalenesulfonate 
• 152406-24-1 4,8-diamino-naphthalene-1-sulfonic acid 
• 72493-43-7 4-acetylamino-8-amino-naphthalene-1-sulfonic acid 
• 7647-01-0 hydrogenchloride 
• 858186-61-5 8-amino-4-hydroxy-naphthalene-1-sulfonic acid 
• 90-15-3 α-naphthol 

Downstream Products

• 22302-65-4 N-(5-hydroxynaphthalen-1-yl)acetamide 
• 76885-03-5 1-Benzoylamino-5-benzoyloxynaphthalene 
• 75528-55-1 N-(5-hydroxynaphthalen-1-yl)benzamide 
• 521964-05-6 N-(5-hydroxy-naphthalen-1-yl)-3,4-dimethoxy-benzamide 
• 1365658-19-0 biphenyl-4-sulfonic acid (5-hydroxynaphthalen-1-yl)-amide 
• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 521964-06-7 3,4-dimethoxy-N-(5-oxiranylmethoxy-naphthalen-1-yl)-benzamide 
• 923275-85-8 5-[4-(5-{2-[2-(2,6-diisopropyl-phenoxy)-ethoxy]-ethoxy}-naphthalen-1-ylethynyl)-phenyl]-2-{4-[2-(2-{4-[tris-(4-tert-butyl-phenyl)-methyl]-phenoxy}-ethoxy)-ethylsulfanyl]-[1,3]dithiol-2-ylidene}-5H-[1,3]dithiolo[4,5-c]pyrrole 
• 923275-87-0 1,4-bis(5-(2-(2-(2,6-diisopropylphenoxy)ethoxy)ethoxy)naphthalene-1-yl)buta-1,3-diyne 
• 923275-95-0 ((5-(2-(2-(2,6-diisopropylphenoxy)ethoxy)ethoxy)naphthalenyl)ethynyl)trimethylsilane 
• 923275-96-1 1-(2-(2-(2,6-diisopropylphenoxy)ethoxy)ethoxy)-5-ethynylnaphthalene 

Relevant articles and documents

Reduction of organic azides to amines using reusable Fe3O 4 nanoparticles in aqueous medium

Aromatic, heteroaromatic and sulfonyl azides were conveniently reduced to the corresponding amines in excellent yields using hydrazine hydrate in the presence of iron oxide nanoparticles. The Fe3O4-MNPs could be easily separated by an external magnet, and recycled ten times without significant loss of the catalytic efficiency. The Royal Society of Chemistry 2013.

Azo dyes derived from 3-amino pyridine in hair dye compositions

A composition for dyeing hair comprises in a cosmetic vehicle at least one dye compound of the formula STR1 wherein B is selected from the group consisting of STR2 and STR3 wherein R is lower alkyl containing 1-4 carbon atoms, R1 is selected from the group consisting of hydrogen, lower alkyl containing 1-4 carbon atoms, lower alkoxy containing 1-4 carbon atoms and chlorine, R2 is selected from the group consisting of hydrogen, methyl and methoxy, R4 is selected from the group consisting of hydrogen, methyl, chlorine, nitro, amino and acetylamino, R3 is hydrogen or together with R4 forms an unsaturated 6 membered ring carrying a hydroxy substituent chelated with one of the nitrogen atoms of the azo link, and STR4 where R5 is selected from the group consisting of hydrogen, -CH3, -C2 H5 and β-hydroxyethyl, and R6 is selected from the group consisting of hydrogen, --CH3, --C2 H5, β-hydroxyethyl, phenyl and -CH2 SO3 Na, With the proviso that when B is STR5 the anion X- associated with the quaternized nitrogen atom is the anion residue of a member selected from the group consisting of organic acid and mineral acid, said composition having a pH ranging from 3 to 11 and said compound being present in an amount ranging from 0.001 to 1 percent by weight of said composition.