5417-63-0

Basic information

• Product Name: 3-AMINO-2-NAPHTHOL
• Synonyms: 2-Naphthalenol, 3-amino-;2-Naphthol, 3-amino-;2-AMINO-3-HYDROXYNAPHTHALENE;3-HYDROXY-2-NAPHTHYLAMINE;3-AMINO-2-NAPHTHOL;3-AMINO-2-HYDROXYNAPHTHALENE;LABOTEST-BB LT00080648;2-Hydroxy-3-aminonaphthalene
• CAS NO: 5417-63-0
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 226-519-4
• Product Categories: Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 5417-63-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 229-230 °C(lit.)
• Boiling Point: 343.5 °C at 760 mmHg
• Flash Point: 161.6 °C
• Appearance: /
• Density: 1.281 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.36±0.40(Predicted)
• CAS DataBase Reference: 3-AMINO-2-NAPHTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-2-NAPHTHOL(5417-63-0)
• EPA Substance Registry System: 3-AMINO-2-NAPHTHOL(5417-63-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-36/37/39-45
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5417-63-0(Hazardous Substances Data)

Usage

Uses

3-Amino-2-naphthol was used in the synthesis of 2-naphthyl-3-NHSO2CF3, 1-naphthyl-5-NHSO2CF3, benzoquinolinequinone and 3-chloro-2-napthol.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 390, 1950 DOI: 10.1021/ja01157a105

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

Upstream product

• 92-44-4 2,3-naphthalenediol 
• 32361-60-7 3-nitro-naphthalen-2-ol 
• 5341-58-2 3-hydroxy-2-naphthohydrazide 
• 6962-30-7 3-hydroxy-2-naphthoyl azide 
• 7147-28-6 3-methoxy-[2]naphthoic acid ethyl ester 
• 58698-35-4 3-methoxy-2-naphthoic hydrazide 
• 883-62-5 3-methoxy-2-naphthoic acid 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 412036-46-5 (3-methoxy-[2]naphthyl)-carbamic acid ethyl ester 
• 608515-85-1 (3-hydroxy-[2]naphthyl)-carbamic acid methyl ester 

Downstream Products

• 109601-89-0 2-naphth[2,3-d]oxazol-2-yl-benzenesulfonic acid 
• 20026-17-9 N-(3-hydroxy-[2]naphthyl)-benzamide 
• 858021-16-6 3-(2,4,6-Trinitro-anilino)-[2]naphthol 
• 771-97-1 2,3-Diaminonaphthalene 
• 103027-41-4 1-(tert-butyldimethylsilyl)-4-(4',4',5',5'-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-5-ol 
• 2036-48-8 2-Phenylazo-3-naphthol 
• 106383-38-4 2-biphenyl-4-yl-naphtho[2,3-d]oxazole 
• 109590-61-6 3-phenyl-2H-naphtho[2,3-b][1,4]-oxazin-2-one 
• 97283-41-5 2-phenyl-2,3-dihydro-naphtho[2,3-d][1,3,2]oxazaborole 
• 41014-41-9 2-(chloromethyl)naphth<2,3-d>oxazole 
• 103086-47-1 2,5-Dichloro-N-(3-hydroxy-naphthalen-2-yl)-benzamide 
• 37038-13-4 dibenzophenoxazine 
• 20686-66-2 2-methylnaphtho[2,3-d]oxazole 

Relevant articles and documents

-

-

Antitumor agents. 5. Synthesis, structure - activity relationships, and biological evaluation of dimethyl-5H-pyridophenoxazin-5-ones, tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-benzopyridophenoxazin-5-ones with potent antiproliferative activity

New antiproliferative compounds, dimethyl-5H-pyrido[3,2-a]phenoxazin-5-ones (1-6), tetrahydro-5H-benzopyrido[2,3-j]phenoxazin-5-ones (7-9), and 5H-benzopyrido[3,2-a]phenoxazin-5-ones (10-12) were synthesized and evaluated against representative human neoplastic cell lines. Dimethyl derivatives 1-6 were more active against carcinoma than leukemia cell lines. The tetrahydrobenzo derivatives 7-9 were scarcely active, whereas the corresponding benzo derivatives 10-12 showed notable cytotoxicity against a majority of the tested cell lines. Molecular modeling studies indicated that the high potency of 10 and 11, the most cytotoxic compounds of the whole series, could be due to the position of the condensed benzene ring, which favors π-π stacking interactions with purine and pyrimidine bases in the DNA active site. Biological studies suggested that 10-12 have no effect on human topoisomerases I and II and that they induce arrest at the G2/M phase.