ChemicalBook > CAS DataBase List > (2-Bromoethyl)benzene

(2-Bromoethyl)benzene

Product Name
(2-Bromoethyl)benzene
CAS No.
103-63-9
Chemical Name
(2-Bromoethyl)benzene
Synonyms
PHENETHYL BROMIDE;2-Phenethyl bromide;2-PHENYLETHYL BROMIDE;1-BROMO-2-PHENYLETHANE;1-phenyl-2-bromoethane;Tetrabomoethane;2-phenethylbromide;-Bromoethylbenzene;β-Bromophenylethane;2-bromoethy benzene
CBNumber
CB0427485
Molecular Formula
C8H9Br
Formula Weight
185.06
MOL File
103-63-9.mol
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(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)
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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)
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B65780
Product name
(2-Bromoethyl)benzene
Purity
98%
Packaging
5g
Price
$43.3
Updated
2024/03/01
Sigma-Aldrich
Product number
1269913
Product name
Fentanyl Related Compound A
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100mg
Price
$520
Updated
2024/03/01
TCI Chemical
Product number
B0594
Product name
(2-Bromoethyl)benzene
Packaging
100G
Price
$38
Updated
2024/03/01
TCI Chemical
Product number
B0594
Product name
(2-Bromoethyl)benzene
Packaging
500G
Price
$98
Updated
2024/03/01
Alfa Aesar
Product number
A12528
Product name
(2-Bromoethyl)benzene, 98%
Packaging
100g
Price
$36.2
Updated
2024/03/01
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(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.]

Toxics Screening Level

The Initial Threshold Screening Level (ITSL) is 2.7 μg/m3 with an annual averaging time.

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

(2-Bromoethyl)benzene Preparation Products And Raw materials

Raw materials

Potassium carbonate Phenethyl alcohol

Preparation Products

1-Phenyl-1,2-ethanediol 1-(2-PHENYLETHYL)PIPERAZINE 4-Vinylbenzyl chloride N-METHYLPHENETHYLAMINE
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View Lastest Price from (2-Bromoethyl)benzene manufacturers

Dorne Chemical Technology co. LTD
Product
(2-Bromoethyl)benzene 103-63-9
Price
US $10.00/ASSAYS
Min. Order
1ASSAYS
Purity
99%
Supply Ability
10 tons
Release date
2024-03-26
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
(2-Bromoethyl)benzene 103-63-9
Price
US $1000.00-800.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-16
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
(2-Bromoethyl)benzene 103-63-9
Price
US $999.00-666.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-13

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