1198-27-2

Basic information

• Product Name: 1-Amino-2-naphthol hydrochloride
• Synonyms: 1-amino-2-naphthohydrochloride;1-AMINO-2-HYDROXYNAPHTHALENE HYDROCHLORIDE;1-AMINO-2-NAPHTHOL HCL;1-AMINO-2-NAPHTHOL HYDROCHLORIDE;2-HYDROXY-1-NAPHTHYLAMINE HYDROCHLORIDE;2-HYDROXY-1-NAPHTHYLAMMONIUM CHLORIDE;TIMTEC-BB SBB000347;1-AMINO-2-NAPHTHOL HYDROCHLORIDE, TECH., 90%
• CAS NO: 1198-27-2
• Molecular Formula: C₁₀H₁₀NO*Cl
• Molecular Weight: 195.65
• EINECS: 214-830-8
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 1198-27-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 250 °C (dec.)(lit.)
• Boiling Point: 336.8°Cat760mmHg
• Flash Point: 157.5°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 5.61E-05mmHg at 25°C
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: Soluble
• Sensitive: Light Sensitive
• BRN: 3699817
• CAS DataBase Reference: 1-Amino-2-naphthol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-2-naphthol hydrochloride(1198-27-2)
• EPA Substance Registry System: 1-Amino-2-naphthol hydrochloride(1198-27-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-27-36/37/39
• WGK Germany: 3
• RTECS: QL3335000
• TSCA: Yes
• Hazardous Substances Data: 1198-27-2(Hazardous Substances Data)

Usage

Chemical Properties

lilac to light grey fluffy powder

Uses

1-Amino-2-naphthol hydrochloride was used in a study on degradation of the azo dye Acid Orange 7 in batch anaerobic unstirred assay.

General Description

1-Amino-2-naphthol undergoes condensation with methylene-substituted azaheterocycles in presence of an oxidizing agent to yield photochromic spirooxazines.

Purification Methods

Crystallise the salt from the minimum volume of hot water containing a few drops of stannous chloride in an equal weight of hydrochloric acid (to reduce atmospheric oxidation). Filter the solution and add half its volume of conc HCl and set aside. The salt crystallises almost quantitatively. Dry it in a vacuum in the dark (m 260o). The salt is more stable than the free base which has m 150o (darkening at 130o) and its O-methyl ether has m 49o and b 159-159o/9mm. [Desai et al. J Chem Soc 324 1938, Beilstein 13 H 666, 13 I 268, 13 II 408, 13 III 1875, 13 IV 2080.]

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

Upstream product

• 633-96-5 orange II 
• 85-85-8 1-(pyridin-2-yl-azo)-2-naphthol 
• 40339-35-3 sudan I 

Downstream Products

• 78659-77-5 2-(4-Dibromomethyl-phenyl)-naphtho[1,2-d]oxazole 
• 1386994-19-9 4-(4-(dimethylamino)benzylideneamino)naphthalene-1,2-dione 
• 1386994-20-2 4-(3,4,5-trimethoxybenzylideneamino)naphthalene-1,2-dione 
• 1386994-21-3 4-(3,4-dimethoxybenzylideneamino)naphthalene-1,2-dione 
• 1386994-22-4 4-(2-nitrobenzylideneamino)naphthalene-1,2-dione 
• 1386994-23-5 4-(4-hydroxy-3-methoxybenzylideneamino)naphthalene-1,2-dione 
• 1386994-24-6 4-(2-hydroxybenzylideneamino)naphthalene-1,2-dione 
• 1386994-26-8 4-((3-phenylallylidene)amino)naphthalene-1,2-dione 
• 1386994-27-9 4-(cyclohexylideneamino)naphthalene-1,2-dione 
• 1386994-11-1 4-(benzylideneamino)naphthalene-1,2-dione 
• 1386994-12-2 4-(4-nitrobenzylideneamino)naphthalene-1,2-dione 
• 524-42-5 1,2-naphthoquinone 
• 1386994-13-3 4-(2,4-dichlorobenzylideneamino)naphthalene-1,2-dione 
• 1386994-14-4 4-(4-hydroxybenzylideneamino)naphthalene-1,2-dione 

Relevant articles and documents

Synthesis, characterization, in vitro anticancer activity, and docking of Schiff bases of 4-amino-1,2-naphthoquinone

A series of Schiff bases of 4-amino-1,2-naphthoquinone were synthesized, purified, characterized, and evaluated for cytotoxicity against a panel of human cancer cell lines (Hep-G2, MG-63, and MCF-7). The cells were dosed with these Schiff bases at varying concentrations, and cell viability was measured by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Significant anticancer activities were observed in vitro for some members of the series and compounds 4-(3,4,5-trimethoxybenzylideneamino) naphthalene-1,2-dione (S10) as well as 4-(4-hydroxy-3-methoxybenzylideneamino) naphthalene-1,2-dione (S13) are active cytotoxic agents against different cancer cell lines with IC50 values in the range of 5.91-9.98 μM. The structures of synthesized compounds were established by spectroscopic (FT-IR, 1H NMR, 13C NMR) and elemental analysis. To study the molecular basis of interaction and affinity of binding of the target molecules, all the compounds were docked into the ATPase domain of Topoisomerase-II (TP-II) by using Schroedinger molecular modeling software package. Docking experiments showed a good correlation between their predicted glide scores and the observed IC50 values of synthesized compounds. Structure-activity relationships indicated that presence of electron donating groups on phenyl ring of Schiff bases enhances the activity but Schiff base with electron withdrawing substituents on phenyl ring shows diminished activity.