(1-Bromoethyl)benzene
[CAS# 585-71-7]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: (1-Bromoethyl)benzene
• Synonyms: alpha-Methylbenzyl bromide
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06
• CAS Registry Number: 585-71-7
• EC Number: 209-560-2
• SMILES: CC(C1=CC=CC=C1)Br

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*, 1.356 g/mL (Expl.)
• Melting point: -65 ºC (Expl.)
• Boiling point: 203.0 ºC 760 mmHg (Calc.)^*, 227.5 ºC (Expl.)
• Flash point: 81.7 ºC (Calc.)^*, 81 ºC (Expl.)
• Index of refraction: 1.552 (Calc.)^*, 1.56 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	4	H227
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

1-Bromoethylbenzene is an organic compound that consists of a benzene ring (C6H5) attached to an ethyl group (C2H5) through a bromine atom (Br). It is classified as an alkyl halide and can be represented by the chemical formula C8H9Br. This compound is widely used in organic synthesis, serving as an intermediate in the production of various chemicals and as a reagent in several types of reactions.

1-Bromoethylbenzene is synthesized by the electrophilic substitution reaction of ethylbenzene with a brominating agent, such as N-bromosuccinimide (NBS) or elemental bromine (Br2). In this reaction, the bromine atom replaces a hydrogen atom on the ethyl group of ethylbenzene, forming the bromoethyl derivative. The reaction is typically carried out in the presence of a suitable solvent and under controlled conditions to ensure the desired substitution occurs.

The primary application of 1-bromoethylbenzene is as a versatile intermediate in the synthesis of other organic compounds. It is used in the preparation of various aromatic compounds through reactions such as nucleophilic substitution or coupling reactions. For example, it can be employed in the synthesis of substituted styrenes, where the ethyl group is replaced by other functional groups. Additionally, it is used in the production of various pharmaceutical and agricultural chemicals, where its ability to undergo electrophilic substitution reactions makes it a valuable building block in the formation of more complex structures.

In the laboratory, 1-bromoethylbenzene is often used as a starting material for the synthesis of various organic intermediates. It can participate in a range of reactions, including the formation of Grignard reagents, which are highly reactive species used in the synthesis of a variety of compounds. Moreover, the bromine atom in 1-bromoethylbenzene makes it an excellent candidate for nucleophilic substitution reactions, where the bromine is replaced by other nucleophiles, such as hydroxyl, amine, or alkoxide groups, depending on the conditions used.

Additionally, 1-bromoethylbenzene finds applications in the production of polymers and copolymers. It can be utilized as a comonomer in the synthesis of styrene-based polymers, which are widely used in the manufacture of plastics and other materials. In these applications, the compound serves to modify the properties of the resulting polymer, such as its flexibility, strength, or chemical resistance.

1-Bromoethylbenzene also serves as a reagent in various chemical processes in research and industrial settings. For example, it can be used in reactions to introduce functional groups into organic molecules, allowing for the design and synthesis of new compounds with specific properties. This versatility in synthetic applications is one of the reasons why 1-bromoethylbenzene is valued in the chemical industry.

Despite its usefulness, 1-bromoethylbenzene should be handled with care, as it is a halogenated organic compound that can pose health and environmental risks. Prolonged exposure to the compound can lead to irritation of the skin, eyes, and respiratory system. In laboratory settings, proper protective equipment, such as gloves, goggles, and adequate ventilation, should be used to minimize exposure. Additionally, its disposal must be done in accordance with environmental regulations to prevent contamination.

In conclusion, 1-bromoethylbenzene is a useful organic compound widely employed in synthetic chemistry for the preparation of various other chemicals. Its role as an intermediate in organic synthesis, its ability to undergo nucleophilic substitution reactions, and its use in polymer production make it a valuable tool in the chemical industry. However, as with many halogenated compounds, it must be handled with care to avoid potential health and environmental hazards.

References

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DOI: 10.1007/bf00664102

2019. Photochemical Organocatalytic Borylation of Alkyl Halides and Sulfonates. Synfacts, 15(09).
DOI: 10.1055/s-0039-1690453

2023. A general copper-catalysed enantioconvergent radical Michaelis�Becker-type C(sp3)�P cross-coupling. Nature Synthesis, 2(4).
DOI: 10.1038/s44160-023-00252-3