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4-Nitrobenzyl Bromide: A Versatile Intermediate fo
4-Nitrobenzyl Bromide: A Versatile Intermediate fo
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Apr 18, 2025
11:08 PM
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Introduction
4-Nitrobenzyl bromide
is a highly reactive benzyl halide widely used in organic synthesis, pharmaceutical research, and chemical manufacturing. Known for its electron-withdrawing nitro group at the para-position, this compound acts as a powerful alkylating agent, enabling the formation of C–N, C–O, and C–S bonds in a variety of chemical transformations.
Chemical Identity
IUPAC Name: 1-(Bromomethyl)-4-nitrobenzene
Common Name: 4-Nitrobenzyl bromide
Molecular Formula: C7H6BrNO2
Molecular Weight: 216.03 g/mol
CAS Number: 1002-83-3
Appearance: Pale yellow to light brown crystalline powder
Solubility: Soluble in most organic solvents like acetone, chloroform, and ethanol
Reactivity and Structure
The para-nitro group enhances the electrophilic character of the benzyl carbon, making 4-nitrobenzyl bromide an excellent substrate for nucleophilic substitution reactions. It reacts readily with:
Amines to form benzylated amines
Alcohols to produce ethers
Thiols to create thioethers
Applications
1. Pharmaceutical Intermediate
4-Nitrobenzyl bromide is used in the synthesis of various bioactive compounds, such as enzyme inhibitors, CNS agents, and antibiotics. It plays a key role in introducing protected benzyl functionalities during multi-step synthesis.
2. Protecting Group Chemistry
The 4-nitrobenzyl group is widely used as a photolabile protecting group, especially for protecting carboxylic acids and amines in peptide and nucleotide chemistry.
3. Material Science and Specialty Chemicals
It is employed in the design of photoresists, photoreactive polymers, and dyes, where its nitro functionality contributes to specific electronic properties.
4. Academic and Industrial R&D
Used in research laboratories for the development of novel molecules and functional materials.
Handling and Storage
Store in a cool, dry place, away from heat and moisture
Handle under inert atmosphere (e.g., nitrogen or argon) when possible
Use appropriate PPE: gloves, lab coat, safety goggles
Avoid inhalation or direct contact with skin
Safety Information
Hazards: Irritant to skin, eyes, and respiratory tract; harmful if swallowed
Risk Phrases: R22 (harmful if swallowed), R36/37/38 (irritating to eyes, respiratory system, and skin)
First Aid: Rinse immediately with water in case of contact; seek medical advice if symptoms persist
Conclusion
4-Nitrobenzyl bromide is a valuable synthetic intermediate that serves a key function in chemical synthesis across multiple industries. Its reactivity, ease of use, and versatility make it a preferred choice for alkylation reactions and photolabile protection strategies.
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