30478-88-7

Basic information

• Product Name: 2-NAPHTHALENOL, 3-BROMO-
• Synonyms: 2-NAPHTHALENOL, 3-BROMO-;3-broMonaphthalen-2-ol;3-Bromo-2-naphthol 99%
• CAS NO: 30478-88-7
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.07
• Product Categories: Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 30478-88-7.mol

Chemical Properties

• Melting Point: 82 °C
• Boiling Point: 313.7°C at 760 mmHg
• Flash Point: 143.5°C
• Appearance: /
• Density: 1.614g/cm³
• Vapor Pressure: 0.000264mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.03±0.40(Predicted)
• CAS DataBase Reference: 2-NAPHTHALENOL, 3-BROMO-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NAPHTHALENOL, 3-BROMO-(30478-88-7)
• EPA Substance Registry System: 2-NAPHTHALENOL, 3-BROMO-(30478-88-7)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 30478-88-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Naphthalenol, 3-bromois used as a key intermediate in the synthesis of various organic compounds, particularly those requiring a brominated naphthalene structure. Its unique chemical properties make it a valuable building block for creating pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Reactions as a Reagent:
In the realm of chemical reactions, 2-Naphthalenol, 3-bromoserves as a reagent, facilitating specific transformations and providing a means to achieve desired products. Its reactivity and selectivity are advantageous in various synthetic routes, contributing to the efficiency and effectiveness of the processes.
Used in Research and Development:
2-Naphthalenol, 3-bromois employed in research and development applications, where its unique structure and properties are explored for potential uses in new chemical entities, materials, or processes. It aids scientists in understanding the behavior of brominated aromatic compounds and their interactions with other molecules, paving the way for innovative discoveries and advancements in the field of chemistry.

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

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 93-18-5 2-ethoxynaphthalene 
• 50389-69-0 2-bromo-3-ethoxynaphthalene 
• 1449272-81-4 N,N-diethyl-O-((3-bromo)naphth-2-yl)-carbamate 
• 67291-63-8 2-amino-3-methoxynaphthalene 
• 13042-06-3 3-methoxy-[2]naphthoic acid amide 
• 135-19-3 β-naphthol 
• 858023-36-6 1,1,3,4,6,7-hexabromo-3,4,6,7-tetrahydro-1H-naphthalen-2-one 
• 54246-03-6 1,1-dibromo-1H-naphthalen-2-one 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 30478-89-8 1,3-dibromonaphthalen-2-ol 
• 33670-69-8 3-bromo-2-hydroxy-naphthalene-1-diazonium-betaine 
• 54245-33-9 3-bromonaphthalen-2-amine 

Downstream Products

• 1611445-43-2 allyl 3-bromo-2-naphthyl ether 
• 1574664-80-4 6-bromo-8,9,10,10a-tetrahydro-7aH-cyclopenta[b]naphtha[1,2-d]furan-7a-ol 
• 486996-45-6 3-bromo-2-hydroxynaphthalene-1-carbaldehyde 
• 1597710-12-7 5-bromo-2-(4-methylbenzoyl)-3H-benzo[f ]chromen-3-one 
• 1556674-35-1 3-phenyl-2H-naphtho[2,3-e][1,4]dioxepin-5(3H)-one 
• 1556674-49-7 3-phenyl-2H-naphtho[2,3-e][1,4]dioxepin-5(3H)-one 

Relevant articles and documents

Bi[naphtho[2,3-b]furanyl]: A versatile organic semiconductor with a furan-furan junction

[2,2′]Bi[naphtho[2,3-b]furanyl] was synthesized, characterized, and examined as an organic semiconductor for thin-film OFETs, bilayer OPVs, and organic light-emitting transistors (OLETs). In the devices, the material acted as a p-type semiconductor, showing moderately high mobility in OFETs, good photo conversion efficiency in OPVs, and blue-green emission in OLETs.

TRICYCLIC FURAN-SUBSTITUTED PIPERIDINEDIONE COMPOUND

Disclosed are a series of tricyclic furan-substituted piperidinedione compounds and an application thereof in preparing a drug for treating a disease related to CRBN protein. In particular, disclosed is a derivative compound represented by formula (I) or a pharmaceutically acceptable salt thereof.

Enhancing the Antiaromaticity ofs-Indacene through Naphthothiophene Fusion

Addressing the instability of antiaromatic compounds often involves protection with bulky groups and/or fusion of aromatic rings, thus decreasing paratropicity. We report four naphthothiophene-fuseds-indacene isomers, one of which is more antiaromatic tha

Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols

An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes

Tuning of the physicochemical properties of the 1,3-diphosphacyclobutane-2,4-diyl unit is attractive in view of materials applications. The use of arynes is shown to be effective for installing relatively electron rich aryl substituents into the open-shell singlet P-heterocyclic system. Treatment of the sterically encumbered 1,3-diphosphacyclobuten-4-yl anion with ortho-silylated aryl triflates in the presence of fluoride under appropriate conditions afforded the corresponding 1-aryl 1,3-diphosphacyclobutane-2,4-diyls. The air-stable open-shell singlet P-heterocycles exhibit considerable electron-donating character, and the aromatic substituent influences the open-shell character, which is thought to be related to the property of p-type semiconductivity. The P-arylated 1,3-diphosphacyclobutane-2,4-diyl systems can be further utilized as detectors of hydrogen fluoride (HF), which causes a remarkable change in their photoabsorption properties.

Reductive cleavage of aryl O-carbamates to phenols by the Schwartz reagent. Expedient link to the directed ortho metalation strategy?

A general, mild, and efficient method for the reductive cleavage of aryl O-carbamates to phenols, 1 → 2 using the Schwartz reagent is reported. The method is selective, tolerating a large number of functional groups; may be carried out by direct or by an economical in situ procedure; and, notably, establishes a synthetic connection to the directed ortho metalation strategy (Figure 1) allowing new entries into difficult to prepare contiguously substituted aromatics and heteroaromatics.

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.