90767-17-2

Basic information

• Product Name: 3-Bromo-1-hydroxynaphthalene
• Synonyms: 3-Bromo-1-hydroxynaphthalene;3-bromonaphthalen-1-ol
• CAS NO: 90767-17-2
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.06598
• Mol File: 90767-17-2.mol

Chemical Properties

• Melting Point: 61 °C
• Boiling Point: 346.8±15.0 °C(Predicted)
• Appearance: /
• Density: 1.614±0.06 g/cm3(Predicted)
• PKA: 8.59±0.40(Predicted)
• CAS DataBase Reference: 3-Bromo-1-hydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-1-hydroxynaphthalene(90767-17-2)
• EPA Substance Registry System: 3-Bromo-1-hydroxynaphthalene(90767-17-2)

Safety Data

• Hazardous Substances Data: 90767-17-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromo-1-hydroxynaphthalene is utilized as a building block in organic synthesis, serving as a key component in the production of a range of pharmaceuticals and agrochemicals. Its structural features make it a versatile intermediate for creating more complex organic compounds.
Used in Research and Development:
In the realm of research and development, 3-Bromo-1-hydroxynaphthalene is employed as a reagent in chemical reactions. It is instrumental in the synthesis of novel compounds and contributes to the advancement of chemical knowledge and innovation.
Used in Material Science and Nanotechnology:
3-Bromo-1-hydroxynaphthalene also holds potential applications in material science and nanotechnology. Its unique chemical properties allow it to be explored for use in the development of new materials with specific characteristics, such as those with enhanced stability or reactivity.
It is crucial to handle 3-Bromo-1-hydroxynaphthalene with care due to its potential hazards if not properly managed, ensuring safety in its applications across different industries.

Upstream product

• 90766-34-0 3-bromonaphthalen-1-amine 
• 776-34-1 1-amino-4-nitronaphthalene 
• 63240-26-6 2-bromo-4-nitronaphthalen-1-amine 
• 102153-47-9 3-bromo-1-nitronaphthalene 
• 13802-40-9 1-Methoxy-3-nitronaphthalene 
• 580-13-2 2-bromonaphthalene 

Downstream Products

• 850650-61-2 3-phenylnaphthalene-1-yl trifluoromethanesulfonate 
• 30069-65-9 3-phenylnaphthalen-1-ol 

Relevant articles and documents

Substituent-induced regioselective hydroxylation of the aromatic C-H bond on naphthalene with metachloroperbenzoic acid catalyzed by F20TPPMnCl

The regioselective hydroxylation of the aromatic C-H bond on a series of naphthalenes with different β-substituent R (R = H, Me, Et, i-Pr, OMe, COOH, Br, etc.) was studied, and the substituent effect on the regioselectivity was investigated. The electron-donating substituent afforded the aromatic C-H bond hydroxylation at the 1α position with more than 80% selectivity, while the electron-withdrawing substituent afforded the aromatic C-H bond hydroxylation at the 4α position with more than 60% selectivity of β-substituted naphthalene hydroxylated with metachloroperbenzoic acid catalyzed by tetrakis(pentafluorophenyl)porphyrin manganese(III) chloride. The research showed that the steric and electronic effects of the substituent appeared to play a significant role in determining the regioselectivity, and the electronic effect was of more importance than the steric effect of the substituent in the current situation. The studies may provide additional proofs for the stepwise mechanism of the aromatic C-H bond hydroxylation through a cationic intermediate. Copyright

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.

SUBSTITUTED 4-ALKOXYOXAZOL DERIVATIVES AS PPAR AGONISTS

The present invention relates to compounds of formula (I) wherein R1 to R8 and n are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.