15231-91-1

Basic information

• Product Name: 6-Bromo-2-naphthol
• Synonyms: 2-Naphthol, 6-bromo-;6-bromo-2-naphthaleno;6-bromo-2-naphtho;6-Bromo-beta-naphthol;Bromo-6 naphtol-2;bromo-6naphtol-2;6-BROMO-2-NAPHTHOL;6-BROMO-2-NAPHTHALENOL
• CAS NO: 15231-91-1
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.07
• EINECS: 239-279-0
• Product Categories: Aromatic Phenols;Heterocycles series;Halides;Phenoles and thiophenoles;Fused Ring Systems;Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 15231-91-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 122-124 °C(lit.)
• Boiling Point: 130°C (rough estimate)
• Flash Point: 167.8 °C
• Appearance: Off-white to beige/Powder
• Density: 1.4412 (rough estimate)
• Vapor Pressure: 1.71E-05mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Chloroform, Methanol
• PKA: 9.26±0.40(Predicted)
• Water Solubility: 不溶于水，溶于醇。
• BRN: 1100270
• CAS DataBase Reference: 6-Bromo-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-naphthol(15231-91-1)
• EPA Substance Registry System: 6-Bromo-2-naphthol(15231-91-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: QL3365000
• Hazardous Substances Data: 15231-91-1(Hazardous Substances Data)

Usage

Chemical Properties

off-white to beige powder

Uses

6-Bromo-2-naphthol is a flavonoid molecule that shows steroid hormone activity and may be useful on anticancer therapy.

Definition

ChEBI: A member of the class of naphthols that is 2-naphthol carrying an additional bromo substituent at position 6.

Purification Methods

Crystallise the naphthol from EtOH or *C6H6/pet ether (m 128o). The benzoyl derivative has m 122o, (from EtOH). [Ruggli & Michels Helv Chim Acta 14 779 1931, Beilstein 6 H 651, 6 II 605, 6 III 2996.]

InChI:InChI=1/C10H7BrO/c11-9-3-1-8-6-10(12)4-2-7(8)5-9/h1-6,12H

Upstream product

• 102153-55-9 3,6-dibromo-[2]naphthol 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 66217-19-4 2-ethoxy-6-bromo-naphthalene 
• 64-17-5 ethanol 
• 16239-18-2 1,6-dibromo-2-naphthol 
• 135-19-3 β-naphthol 
• 98994-65-1 1,3,4,6-tetrabromo-[2]naphthol 
• 116632-10-1 1,4,6-tribromo-[2]naphthol 
• 102153-54-8 4,6-dibromo-β-naphthol 
• 610277-16-2 6-bromo-2-methoxy-1-naphthoic acid 
• 4133-35-1 6-bromo-2-tetralone 
• 1123760-77-9 C₁₀H₉BrO₂ 

Downstream Products

• 202831-66-1 6-bromo-N-phenylnaphthalene-2-amine 
• 209002-38-0 (6-bromo-[2]naphthyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 25696-57-5 (6-bromo-[2]naphthyl)-α-D-glucopyranoside 
• 15572-30-2 6-bromo-2-naphthyl β-D-galactopyranoside 
• 38710-87-1 5-(6-Bromo-naphthalen-2-yloxy)-2-nitro-benzonitrile 
• 77065-79-3 1-benzoyloxy-6-bromo-[2]naphthol 
• 77065-80-6 C₂₄H₁₅BrO₅ 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 74634-34-7 6-bromonaphthalen-2-yl benzoate 
• 475278-17-2 6-phenylnaphthalen-2-ol 
• 874365-08-9 1,4-di-(8-bromo-3-p-methoxyphenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-10-3 1,3-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-07-8 1,4-di-(8-bromo-3-p-fluorophenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 
• 874365-06-7 1,4-di-(8-bromo-3-phenyl-[3H]-naphtho[2,1-b]pyran-3-yl)-benzene 

Relevant articles and documents

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Reductive dehalogenation of halophenols in sulfite-bisulfate medium

The KHSO4-Na2SO3 system is found to be simple and inexpensive for reductive elimination of halogens (Br, I) from the corresponding halophenols under reflux conditions in dry methanol. Under similar conditions the reaction is sluggish with chlorophenols.

Synthesis and antitumor effects of novel benzyl naphthyl sulfoxide/sulfone derivatives derived from Rigosertib

In this work, a series of novel benzyl naphthyl sulfoxides/sulfones derived from Rigosertib were designed and synthesized as potential antitumor agents. The in vitro cytotoxicity against four human cancer cell lines (HeLa, MCF-7, HepG2 and SCC-15) and two normal human cell lines (HUVEC and 293T) indicated that some of the sulfones and sulfoxides possessed potent antineoplastic activity that reached nanomolar levels and relatively low toxicity to normal cells. Among them, (2-methoxy-5-((naphthalen-2-ylsulfonyl)methyl)phenyl)glycine (15b) was found to be a promising antitumor drug candidate that could significantly inhibit tumor cell migration and induce tumor cell apoptosis via the p53-Bcl-2-Bax signaling pathway at nanomolar concentrations.

NAPHTHALENE-CONTAINING POLYMERS AND METHODS OF MAKING THE SAME

The present disclosure relates to a dimer that includes a first hydroxyl-functionalized naphthalene group and a second hydroxyl-functionalized naphthalene group, where the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group. The present disclosure also relates to a polymer synthesized using the dimer, as well as methods for synthesizing both the dimer and the polymer.

A conjugated system of curcumin analogs increase and its preparation method and application

The invention discloses a curcumin analogue with an enlarged conjugated system and a preparation method and application thereof. The structural feature of the curcumin analogue is shown in the general formula (I), wherein R1 is hydrogen and methoxyl, R2 is hydrogen, hydroxy and methoxyl, and two naphthalene nucleuses are connected through a 1,6-heptadiene-3,5-diketone joining chain. The naphthol is used as a raw material, the naphthalene nucleus curcumin analogue with the superior activity for hepatoma carcinoma cell HepG2 cell proliferation is synthesized, and the activity of the curcumin analogue is superior to that of natural curcumin. The curcumin analogue with the enlarged conjugated system has the great significance in guiding discovery of prodrugs and designing lead compounds.