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Here's a concise explanation of 1-Bromoethyl acetate:
1-Bromoethyl acetate (CH₃C(O)OCHBrCH₃, C₄H₇BrO₂) is a reactive organic compound used as a versatile synthetic reagent. It's typically prepared by reacting acetaldehyde with acetic acid and bromine.
Its primary function is as an acetyl group transfer agent. The bromine atom is easily displaced by nucleophiles (like amines or alcohols), facilitating the transfer of the acetyl group (CH₃C(O)-) to form esters or amides. It can also serve as a masked source of acetaldehyde.
Properties: A volatile, moisture-sensitive liquid with a pungent, tear-inducing (lachrymatory) odor. It decomposes easily, releasing acetaldehyde.
Handling: Requires a fume hood due to its reactivity, toxicity, and irritant properties.
1-Bromoethyl acetate (C₄H₇BrO₂) is a reactive organic compound primarily used as a synthetic reagent in organic chemistry. Here are its key characteristics:
Structure: An ester where the acetyl group (CH₃COO-) is attached to a 1-bromoethyl group (-CHBrCH₃). It's often written as CH₃C(O)OCHBrCH₃.
Preparation: Typically made by acetoxybromination of acetaldehyde (CH₃CHO) using acetic acid (CH₃COOH) and bromine (Br₂) or HBr/Ac₂O.
Key Reactivity & Uses:
Acetylating Agent: The bromine atom is easily displaced by nucleophiles (Nu⁻), generating an unstable acetoxonium ion intermediate (CH₃C⁺(OEt)). This readily transfers the acetyl group (CH₃CO-) to the nucleophile, forming esters or amides:CH₃C(O)OCHBrCH₃ + Nu⁻ → CH₃C(O)Nu + CH₃CHO + Br⁻
Source of Acetaldehyde: Hydrolysis releases acetaldehyde.
Building Block: Used to synthesize other compounds like α-acetoxy ketones.
Properties: A volatile, moisture-sensitive liquid with a pungent, lachrymatory odor (causes tears). Boils around ~145-155°C.
Handling: Requires care due to its reactivity, lachrymatory nature, and potential decomposition. Use in a fume hood is essential.
In short: 1-Bromoethyl acetate is a versatile reagent valued for its ability to efficiently transfer an acetyl group (CH₃CO-) to nucleophiles in synthesis.
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