(2-Bromoethyl)benzene Property

Melting point:

-56 °C

Boiling point:

220-221 °C(lit.)

Density 

1.355 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.556(lit.)

Flash point:

193 °F

storage temp. 

2-8°C

solubility 

0.039g/l

form 

Liquid

color 

Clear colorless to pale yellow

Water Solubility 

INSOLUBLE

BRN 

507487

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

WMPPDTMATNBGJN-UHFFFAOYSA-N

CAS DataBase Reference

103-63-9(CAS DataBase Reference)

NIST Chemistry Reference

1-Bromo-2-phenylethane(103-63-9)

EPA Substance Registry System

Benzene, (2-bromoethyl)- (103-63-9)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36-36/37/38

Safety Statements 

26-37/39-39

RIDADR 

UN 1993 / PGIII

WGK Germany 

3

RTECS 

CY9032000

TSCA 

Yes

HS Code 

29036990

Hazardous Substances Data

103-63-9(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

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

(2-Bromoethyl)benzene Chemical Properties,Usage,Production

Description

Phenethylbromide is an analytical reference material that is structurally categorized as an organobromide. It is used in the synthesis of a variety of compounds, including fentanyl. Phenethylbromide is combined with 4-piperidinone to produce N-phenethyl-4-piperidone, which, as a precursor in the synthesis of fentanyl, is scheduled as a List I chemical in the United States. Phenethylbromide may be found as in impurity in samples of fentanyl produced using this pathway.

Chemical Properties

colourless to yellow liquid. It is miscible with ether and benzene, but insoluble in water.

Uses

(2-Bromoethyl)benzene is used in the preparation of phenelzine by reacting with hydrazine. It is also used as a starting material to prepare various beta-phenethyl derivatives, active pharmaceutical ingredients, and fragrances. It finds application as a flame retardant.

Uses

(2-Bromoethyl)benzene is an important starting material for the production of various b-phenethyl derivatives, pharmaceuticals, fragrances, and other fine chemicals.

Preparation

(2-Bromoethyl)benzene is synthesized by the reaction of phenethyl alcohol with hydrogen bromide.
Reaction: The phenethyl alcohol was heated to 110°C, hydrogen bromide was slowly introduced, and the reaction was refluxed. The reaction was completed, cooled, washed with water, 10% sodium carbonate solution, and water in turn. After drying with anhydrous potassium carbonate, fractional distillation under reduced pressure was carried out to collect fractions at 97-99°C (2.0 kPa) with a yield of over 90%.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 2317, 1964 DOI: 10.1021/jo01031a051
Synthetic Communications, 20, p. 2349, 1990 DOI: 10.1080/00397919008053179

Safety

Store at 2-8° C in a tightly closed container in a dry, well-ventilated place. Containers that are opened must be carefully resealed and kept upright to prevent leakage. (2-Bromoethyl)benzene is incompatible with strong oxidizing agents. This chemical is harmful if swallowed and causes severe eye irritation.

Synthesis

Phenethylbromide is commonly synthesized through the addition of HBr to styrene via a free-radical reaction. This process is typically carried out in a glasslined reactor by introducing gaseous HBr into a solution of styrene in an inert solvent that contains a free-radical initiator. The reaction, which is fast and releases a moderate amount of heat, can be managed by introducing HBr at a rate that matches its consumption. Once all the styrene has been converted, any remaining excess HBr can be reclaimed using different methods before the solvent and product are recovered through distillation.

Purification Methods

Wash the bromide with conc H2SO4, water, aqueous 10% Na2CO3 and water again, then dry it with CaCl2 and fractionally distil it just before use. [Beilstein 5 IV 907.]

References

1. Shukla, P.; Sharma, A.; Pallavi, B.; Cheng, C. H. Nickel-catalyzed reductive Heck type coupling of saturated alkyl halides with acrylates and oxabenzonorbornadiene. Tetrahedron 2015, 71 (15), 2260-2266. DOI:10.1016/J.TET.2015.02.067
2. Huang, Y. B.; Yan, L.; Chen, M. Y.; Guo, Q. X.; Fu, Y. Selective hydrogenolysis of phenols and phenyl ethers to arenes through direct C-O cleavage over ruthenium-tungsten bifunctional catalysts. Green Chem. 2015, 17 (5), 3010-3017. DOI:10.1039/C5GC00326A
3. Justice, D.E.A.D.o. Control of a chemical precursor used in the illicit manufacture of fentanyl as a List I chemical. Final rule. Federal Register 73(144), 43355-43357 (2008). PMID: 18949877