4-NITROBENZYL BROMIDE: A VERSATILE BUILDING BLOCK IN ORGANIC SYNTHESIS

4-Nitrobenzyl Bromide: A Versatile Building Block in Organic Synthesis

4-Nitrobenzyl Bromide: A Versatile Building Block in Organic Synthesis

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Introduction


4-Nitrobenzyl bromide is an important organic intermediate widely used in chemical synthesis, particularly in the fields of pharmaceuticals, agrochemicals, and materials science. This compound is valued for its reactivity, which is primarily attributed to the presence of both a benzyl bromide moiety and an electron-withdrawing nitro group at the para-position.





Chemical Identity



  • Chemical Name: 4-Nitrobenzyl bromide

  • Molecular Formula: C7H6BrNO2

  • Molecular Weight: 216.03 g/mol

  • CAS Number: 100-11-8

  • Appearance: Pale yellow to light brown crystalline powder

  • Solubility: Soluble in organic solvents like acetone, ether, and ethanol; slightly soluble in water







Structure and Reactivity


The molecule consists of a benzyl bromide group (–CH2Br) attached to a benzene ring with a para-nitro substituent (–NO2). This structure facilitates:

  • Nucleophilic substitution reactions, where the bromide acts as a good leaving group

  • Photolabile protection, often used in photochemistry and photolabile protecting groups (PPGs)







Applications of 4-Nitrobenzyl Bromide


1. Pharmaceutical Intermediate


Used in the synthesis of bioactive molecules and active pharmaceutical ingredients (APIs), especially for compounds requiring selective benzylation.

2. Protecting Group in Organic Chemistry


Serves as a photolabile protecting group (PPG) for alcohols, carboxylic acids, and amines in complex synthesis workflows.

3. Chemical Probes and Fluorophores


Utilized in the design of chemical sensors and fluorogenic substrates, especially in biological labeling and molecular imaging.

4. Agrochemical Synthesis


Plays a role in the production of specific pesticides and herbicides, due to its reactivity with amines and thiols.

5. Material Science


Acts as a cross-linking or surface modification agent in polymer chemistry and nanomaterial development.





Safety and Handling



  • Hazards: Harmful if inhaled or absorbed through skin; causes irritation to eyes, skin, and respiratory tract

  • Precautions: Handle with protective gloves, goggles, and lab coat in a well-ventilated environment or fume hood

  • Storage: Store in a cool, dry place, away from moisture and strong bases or oxidizing agents







Packaging & Supply


4-Nitrobenzyl bromide is available in:

  • Small-scale research packs (5g, 25g, 100g)

  • Bulk containers (1kg, 5kg, 25kg drums)


All shipments include COA, MSDS, and custom packaging options upon request.





Conclusion


4-Nitrobenzyl bromide is a highly versatile reagent valued for its strong electrophilicity and the ability to participate in diverse synthetic reactions. Whether for laboratory research or industrial production, it remains a vital tool in modern chemistry.

Looking for bulk or lab-grade 4-Nitrobenzyl Bromide? Contact us for pricing, lead time, and regulatory documentation.

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