(2-Bromoethyl)benzene
[CAS# 103-63-9]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: (2-Bromoethyl)benzene
• Synonyms: 1-Bromo-2-phenylethane; beta-Bromophenylethane; Phenethyl bromide
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• CAS Registry Number: 103-63-9
• EC Number: 203-130-8
• SMILES: C1=CC=C(C=C1)CCBr

Properties

• Density: 1.355
• Melting point: -56 °C
• Boiling point: 220-221 °C
• Refractive index: 1.5553-1.5573
• Flash point: 89 °C
• Water solubility: INSOLUBLE

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

(2-Bromoethyl)benzene, also known as phenethyl bromide, is an organobromine compound with the molecular formula C8H9Br. This chemical was first synthesized in the late 19th century as part of the broader exploration of halogenated hydrocarbons. Early research aimed to understand the reactivity and properties of benzene derivatives. (2-Bromoethyl)benzene is produced through the bromination of ethylbenzene, a reaction facilitated by the presence of light or a radical initiator.

One of the primary applications of (2-Bromoethyl)benzene is in the pharmaceutical industry. It serves as a crucial building block in the synthesis of various drugs and active pharmaceutical ingredients (APIs). Its ability to undergo nucleophilic substitution reactions makes it valuable for creating complex molecular structures necessary for therapeutic agents. For instance, it is used in the synthesis of beta-blockers, antihistamines, and other medications.

(2-Bromoethyl)benzene is also employed in the production of agrochemicals, including herbicides, insecticides, and fungicides. Its bromine moiety enhances the biological activity of these compounds, making them more effective in protecting crops from pests and diseases. The chemical's reactivity allows for the modification of agrochemical structures, optimizing their efficacy and stability.

In organic synthesis, (2-Bromoethyl)benzene is used as an intermediate to construct more complex molecules. Its ability to participate in various chemical reactions, such as Grignard reactions, Friedel-Crafts alkylations, and coupling reactions, makes it a versatile reagent in synthetic chemistry.

(2-Bromoethyl)benzene is used in material science for the development of polymers and advanced materials. It acts as a precursor in the synthesis of functionalized polymers, where its bromine atom can be replaced with other groups to tailor the material's properties. These polymers are used in coatings, adhesives, and electronic materials, where specific characteristics such as conductivity, adhesion, and thermal stability are required.

In research and development, (2-Bromoethyl)benzene is employed in the study of reaction mechanisms and the development of new synthetic methodologies. Its well-characterized reactivity provides a reliable model for exploring chemical transformations and optimizing reaction conditions.

References

2020. Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N-Iodosuccinimide. Synthesis, 52(06).
DOI: 10.1055/s-0039-1691642

2024. Synthesis of chiral 2-(N-Boc-azetidin-3-yl)-2-alkylpropanoic acids as novel GABA derivatives. Monatshefte für Chemie - Chemical Monthly, 155(1).
DOI: 10.1007/s00706-023-03149-1

2024. Adenine derivatives as inhibitors of the casein kinase CK1delta enzyme. Medicinal Chemistry Research, 33(4).
DOI: 10.1007/s00044-024-03202-6