1-Bromonaphthalene

Synonym(s):α-Naphthyl bromide;1-Bromonaphthalene

CAS NO.：90-11-9
Empirical Formula: C10H7Br
Molecular Weight: 207.07
MDL number: MFCD00003868
EINECS: 201-965-2
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-24 21:11:45

What is 1-Bromonaphthalene?

Chemical properties

Thick colorless yellow to yellow-brown liquid with a pungent odor. Insoluble in water, miscible with alcohol, ether, benzene and chloroform. 1-Bromonaphthalene is one of two isomeric bromonaphthalenes, the other being 2-bromonaphthalene.

The Uses of 1-Bromonaphthalene

1-Bromonaphthalene is used in organic synthesis and refractometry of fats. It is used in the preparation of N-aryl imidazoles and diaryl ethers. It is used to determine the refractive index of crystals and the water content of alcohols. It is utilized in the preparation of glutathione peroxidase-like antioxidant activity of diaryl diselenides. Further, it serves as a solvent for the exfoliation and dispersion of hexabenzocoronene. In addition to this, it is used as a refrigerant and a solvent molecular weight substance.

Preparation

1-Bromonaphthalene is synthesized by the reaction of naphthalene with bromine: C10H8+ Br2→ C10H7Br + HBr.
Reaction: add carbon tetrachloride and naphthalene in the reaction pot, stirring and heating, and slowly add bromine at 45℃. After adding, keep the reaction at 70-80℃ for 3-4h. distillation to recover carbon tetrachloride, wash the reaction product, distill under reduced pressure, wash again, filter, dry and get the finished product.

What are the applications of Application

1-Bromonaphthalene is a bromoarene that can be used in:
Palladium-catalyzed Suzuki–Miyaura coupling reaction with potassium aryltrifluoroborates without the use of phase-transfer catalysts or phosphine ligands.
The preparation of indeno annelated polycyclic aromatic hydrocarbons by reacting with o-bromobenzeneboronic acid and oligocyclic bromoarenes via Suzuki-Heck type coupling.
Ni catalyzed Kumada–Tamao–Corriu cross-coupling reaction with PhMgBr.
The preparation of arylnaphthalenes via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with aryl boronic acid.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 121, 1941
Tetrahedron, 64, p. 4999, 2008 DOI: 10.1016/j.tet.2008.03.085

General Description

The vibrational spectra of 1-bromonaphthalene has been studied.

Purification Methods

Purify 1-bromonaphthalene by passage through activated alumina, and three vacuum distillations. [Beilstein 5 H 547, 5 IV 1665.]

Properties of 1-Bromonaphthalene

Melting point:	−2-−1 °C(lit.)
Boiling point:	133-134 °C10 mm Hg(lit.)
Density	1.48 g/mL at 20 °C(lit.)
vapor pressure	0.013 hPa (20 °C)
refractive index	n20/D 1.6570(lit.)
Flash point:	>230 °F
storage temp.	Store below +30°C.
solubility	H2O: slightly soluble
form	Liquid
color	slightly yellow to deep brownish-yellow
Water Solubility	slightly soluble
Merck	14,1425
BRN	1906414
Dielectric constant	5.1（19℃）
CAS DataBase Reference	90-11-9(CAS DataBase Reference)
NIST Chemistry Reference	Naphthalene, 1-bromo-(90-11-9)
EPA Substance Registry System	Naphthalene, 1-bromo- (90-11-9)

Safety information for 1-Bromonaphthalene

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Environment GHS09
GHS Hazard Statements	H302:Acute toxicity,oral H319:Serious eye damage/eye irritation H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.