91270-68-7

Basic information

• Product Name: 6-Bromo-1-hydroxynaphthalene
• Synonyms: 6-Bromo-1-hydroxynaphthalene;6-broMonaphthalen-1-ol;6-BROMO-1-HYDROXYNAPHTHALENE, 6-Bromonaphthalen-1-ol;6-Bromo-1-hydroxyphthalene
• CAS NO: 91270-68-7
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.06598
• Mol File: 91270-68-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 128.5-129.5 °C
• Boiling Point: 353.821°C at 760 mmHg
• Flash Point: 167.785°C
• Appearance: /
• Density: 1.615g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.705
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.93±0.40(Predicted)
• CAS DataBase Reference: 6-Bromo-1-hydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-1-hydroxynaphthalene(91270-68-7)
• EPA Substance Registry System: 6-Bromo-1-hydroxynaphthalene(91270-68-7)

Safety Data

• Hazardous Substances Data: 91270-68-7(Hazardous Substances Data)

Usage

General Description

6-Bromo-1-hydroxynaphthalene, also known as 1-Hydroxy-6-bromonaphthalene, is an organic compound with the formula C10H7BrO. It is a derivative of naphthalene and is primarily used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. The presence of a hydroxyl group and a bromine atom on the naphthalene ring makes it a valuable building block for organic synthesis. It is also used in the production of dyes, agrochemicals, and other specialty chemicals. 6-Bromo-1-hydroxynaphthalene is a white to off-white crystalline solid with a melting point of around 157-159°C and is considered to be of low toxicity.

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

Upstream product

• 1123760-77-9 C₁₀H₉BrO₂ 

Downstream Products

• 1426082-26-9 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol 
• 1426082-27-0 2-chloro-6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 698370-64-8 6-bromo-2-[(N,N-dibenzylamino)methyl]naphthalen-1-ol 
• 24894-78-8 6-methylnaphthalen-1-ol 
• 54828-63-6 6-methoxy-2-bromonaphthalene 

Relevant articles and documents

Acid-catalyzed dehydration of naphthalene-cis-1,2-dihydrodiols: Origin of impaired resonance effect of 3-substituents

Acid-catalyzed dehydrations of substituted naphthalene-cis-1,2-dihydrodiols occur with loss of the 1- or 2-OH group to form 2- and 1-naphthols, respectively. Effects of substituents MeO, Me, H, F, Br, I, and CN at 3-, 6-, and 7-positions of the naphthalene ring are consistent with rate-determining formation of β-hydroxynaphthalenium ion (carbocation) intermediates. For reaction of the 1-hydroxyl group the 3-substituents are correlated by the Yukawa-Tsuno relationship with ρ = -4.7 and r = 0.25 or by σp constants with ρ = -4.25; for reaction of the 2-hydroxyl group the 3-substituents are correlated by σm constants with ρ = -8.1. The correlations for the 1-hydroxyl imply a surprisingly weak resonance interaction of +M substituents (MeO, Me) with a carbocation reaction center but are consistent with the corresponding correlation for acid-catalyzed dehydration of 3-substituted benzene-cis-1,2-dihydrodiols for which ρ = -6.9 and r = 0.43. Substituents at the 6- and 7-positions of the naphthalene rings by contrast are correlated by σ+ with ρ = -3.2 for reaction of the 1-hydroxyl group and ρ = -2.7 for reaction of the 2-hydroxyl group. The unimpaired resonance implied by these substituent effects appears to be inconsistent with a previous explanation of the weak resonance of the 3-substituents in terms of imbalance of charge development and/or nonplanarity of the benzenium ring in the transition state. An alternative possibility is that the adjacent hydroxyl group interferes sterically with conjugation of +M substituents. "Hyperaromaticity" of the arenium ion intermediates does not appear to be a factor influencing this behavior.