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(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
Molecular Weight:
185.06
MDL Number:
MFCD00000240
MOL File:
103-63-9.mol
MSDS File:
SDS
Last updated:2024-05-16 10:38:43

(2-Bromoethyl)benzene Properties

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)
EWG's Food Scores 1
FDA UNII 96O442668X
NIST Chemistry Reference 1-Bromo-2-phenylethane(103-63-9)
EPA Substance Registry System Benzene, (2-bromoethyl)- (103-63-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H319
Precautionary statements  P301+P312+P330-P305+P351+P338
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
NFPA 704
2
1 0

(2-Bromoethyl)benzene price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B65780 (2-Bromoethyl)benzene 98% 103-63-9 5g $43.3 2024-03-01 Buy
Sigma-Aldrich 1269913 Fentanyl Related Compound A United States Pharmacopeia (USP) Reference Standard 103-63-9 100mg $520 2024-03-01 Buy
TCI Chemical B0594 (2-Bromoethyl)benzene 103-63-9 100G $38 2024-03-01 Buy
TCI Chemical B0594 (2-Bromoethyl)benzene 103-63-9 500G $98 2024-03-01 Buy
Alfa Aesar A12528 (2-Bromoethyl)benzene, 98% 103-63-9 100g $36.2 2024-03-01 Buy
Product number Packaging Price Buy
B65780 5g $43.3 Buy
1269913 100mg $520 Buy
B0594 100G $38 Buy
B0594 500G $98 Buy
A12528 100g $36.2 Buy

(2-Bromoethyl)benzene Chemical Properties,Uses,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

60-12-8
103-63-9
Synthesis of (2-Bromoethyl)benzene from Phenethyl alcohol
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View Lastest Price from (2-Bromoethyl)benzene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(2-Bromoethyl)benzene pictures 2024-05-27 (2-Bromoethyl)benzene
103-63-9
US $10.00 / G 1G 99% 20 CONTIDE BIOTECH CO.,LTD
(2-Bromoethyl)benzene pictures 2024-05-27 (2-Bromoethyl)benzene
103-63-9
US $30.00 / kg 1kg 98% 2000kg hebei hongtan Biotechnology Co., Ltd
(2-Bromoethyl)benzene pictures 2024-05-27 (2-Bromoethyl)benzene
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US $10.00 / ASSAYS 1ASSAYS 99% 10 tons Dorne Chemical Technology co. LTD
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