1-Bromonaphthalene
Catalog Number
ACM90119
CAS
90-11-9
IUPAC Name
1-bromonaphthalene
Application
1-Bromonaphthalene is a versatile chemical compound primarily used in organic synthesis and refractometry. It plays a crucial role in the preparation of N-aryl imidazoles, diaryl ethers, and compounds exhibiting glutathione peroxidase-like antioxidant activity, such as diaryl diselenides. This colorless to yellow-brown liquid seamlessly integrates with alcohol, ether, benzene, and chloroform, although it remains insoluble in water. Additionally, 1-bromonaphthalene serves as an essential medium for determining crystal refractive indices and the water content in alcohols. Its solvent properties facilitate the exfoliation and dispersion of hexabenzocoronene and its utility as a refrigerant. Moreover, in chemical synthesis, it supports palladium-catalyzed Suzuki-Miyaura coupling reactions, both with potassium aryltrifluoroborates and aryl boronic acids, to produce arylnaphthalenes without the need for phase-transfer catalysts or phosphine ligands. It also participates in nickel-catalyzed Kumada-Tamao-Corriu cross-coupling reactions and aids in forming indeno annelated polycyclic aromatic hydrocarbons.
Molecular Weight
207.07
Molecular Formula
C10H7Br
Product Information
Canonical SMILES
C1=CC=C2C(=C1)C=CC=C2Br
InChI
InChI=1S/C10H7Br/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
InChI Key
DLKQHBOKULLWDQ-UHFFFAOYSA-N
Boiling Point
282 °C
Melting Point
-2 °C
Purity
>95.0%(GC)
Appearance
Colorless to Light orange to Yellow clear liquid
Storage
Keep in dark place. Sealed in dry. Room temperature.
Complexity
133
Exact Mass
205.97311g/mol
Hazard Statements
H302 : Harmful if swallowed.H319 : Causes serious eye irritation.
Heavy Atom Count
11
MDL Number
MFCD00003868
Monoisotopic Mass
205.97311g/mol
Precautionary Statements
P501 : Dispose of contents/ container to an approved waste disposal plant.P270 : Do not eat, drink or smoke when using this product.P264 : Wash skin thoroughly after handling.P280 : Wear eye protection/ face protection.P337 + P313 : If eye irritation persists: Get medical advice/ attention.P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
Reaxys Registry Number
1906414
Refractive Index
1.66
Rotatable Bond Count
0
Signal Word
Warning
Solubility In Water
Slightly soluble
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