1-Bromonaphthalene Chemical Properties

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℃）

InChIKey

DLKQHBOKULLWDQ-UHFFFAOYSA-N

LogP

4.06

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

Hazard Codes 

Xn,Xi

Risk Statements 

22-36-36/37/38-20/21/22

Safety Statements 

26-36

RIDADR 

2810

WGK Germany 

3

RTECS 

QJ1545000

F 

8

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29036990

Toxicity

LD50 orally in Rabbit: 810 mg/kg

MSDS

• Language:English Provider:alpha-Bromonaphthalene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Bromonaphthalene Usage And Synthesis

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.

Uses

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.

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.]

1-Bromonaphthalene(90-11-9)Related Product Information

• b-Bromonaphthalene,2-BROMONAPHTHALENE,BETA-BROMONAPHTHALENE,BROMONAPHTHALENE(2-)
• Sodium bromide
• Phosphorus tribromide
• Bromocyclopentane
• Tetrabutylammonium bromide
• Cuprous bromide
• Potassium bromide
• 1-Bromo-2-methylpropane
• 1-Hexadecylpyridinium bromide
• beta-Bromostyrene
• Boron tribromide
• Hydrogen bromide
• Ammonium bromide
• 1-Bromododecane
• 1-Bromohexadecane
• Calcium bromide
• 1-Bromo-3-methylbutane
• 6-Bromonaphthalene-2-ol,6-Hydroxy-2-bromonaphthalene