1-Bromonaphthalene Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Bromonaphthalene Chemical Properties,Usage,Production

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.]