Chemical Name: 4-Nitrobenzyl Bromide
Molecular Formula: C7H6BrNO2
CAS Number: 100-11-8
Molecular Weight: 216.03 g/mol
Appearance: Pale yellow crystalline solid
Melting Point: 102-106°C
Boiling Point: 289°C (decomposes)
Solubility: Slightly soluble in water; soluble in organic solvents like ethanol, acetone, and ether
Table of Contents
| Section | Details |
|---|---|
| 1. Introduction | Overview of 4-Nitrobenzyl Bromide, including its chemical structure and importance in organic chemistry |
| 2. Chemical Properties | Detailed description of the key chemical and physical properties of 4-Nitrobenzyl Bromide |
| 3. Synthesis and Production | Overview of the common methods used for the synthesis of 4-Nitrobenzyl Bromide |
| 4. Applications | Description of the primary applications of 4-Nitrobenzyl Bromide in pharmaceuticals, organic synthesis, and other industries |
| 5. Reactivity and Derivatives | Discussion of the reactivity of 4-Nitrobenzyl Bromide and the potential derivatives that can be synthesized |
| 6. Safety and Handling | Guidelines on safe handling, storage, and disposal of 4-Nitrobenzyl Bromide |
| 7. Environmental Impact | Information on the environmental considerations associated with the use of 4-Nitrobenzyl Bromide |
| 8. Safety Data | Hazard classifications, pictograms, precautionary statements, and relevant safety data |
| 9. Research and Studies | Summary of recent research and studies involving 4-Nitrobenzyl Bromide |
| 10. Conclusion | Final thoughts on the importance and applications of 4-Nitrobenzyl Bromide |
1. Introduction
4-Nitrobenzyl Bromide is an important organic compound used widely in the field of synthetic chemistry. It belongs to the family of nitrobenzyl halides, where the bromine atom is attached to a benzyl group bearing a nitro substituent at the para position. This structural configuration imparts unique reactivity, making 4-Nitrobenzyl Bromide a valuable reagent in various organic transformations, particularly in the synthesis of protected intermediates, pharmaceuticals, and fine chemicals.
2. Chemical Properties
- Molecular Formula: C7H6BrNO2
- Molecular Weight: 216.03 g/mol
- CAS Number: 100-11-8
- Appearance: Pale yellow crystalline solid
- Melting Point: 102-106°C
- Boiling Point: 289°C (decomposes)
- Solubility: Slightly soluble in water; soluble in organic solvents like ethanol, acetone, and ether
These properties highlight the compound’s utility in organic synthesis, where its solubility in various organic solvents facilitates its use in a range of reaction conditions. The nitro group enhances the electron-withdrawing capacity of the molecule, making it reactive under specific conditions.
3. Synthesis and Production
4-Nitrobenzyl Bromide can be synthesized through the bromination of 4-nitrotoluene. This process typically involves the use of bromine or a brominating agent such as N-bromosuccinimide (NBS) in the presence of a catalyst, often under controlled temperatures to ensure the selective bromination at the benzyl position. After the reaction, the product is purified by recrystallization from a suitable solvent to achieve the desired purity.
4. Applications
4-Nitrobenzyl Bromide is utilized in a variety of synthetic applications, particularly in the pharmaceutical and chemical industries:
- Pharmaceutical Industry: It serves as an intermediate in the synthesis of drugs and bioactive molecules. Its ability to introduce a benzyl protecting group is particularly valuable in the stepwise synthesis of complex molecules, allowing for the selective protection and deprotection of functional groups.
- Organic Synthesis: In organic chemistry, 4-Nitrobenzyl Bromide is used as a protecting group reagent. The nitrobenzyl group can be easily removed under mild conditions, making it ideal for protecting sensitive functional groups during multi-step syntheses.
- Material Science: The compound is also used in the preparation of specialized materials, including polymers and resins, where its unique structure can impart desired physical and chemical properties.
5. Reactivity and Derivatives
The reactivity of 4-Nitrobenzyl Bromide is influenced by the electron-withdrawing nitro group, which makes the benzyl bromide moiety more susceptible to nucleophilic substitution reactions. This allows for the formation of a wide variety of derivatives, including ethers, amines, and esters, which can be further utilized in the synthesis of complex organic molecules. The compound’s reactivity is also exploited in cross-coupling reactions and other transformations that require selective benzylation.
6. Safety and Handling
4-Nitrobenzyl Bromide should be handled with caution due to its potential health hazards. It can cause skin, eye, and respiratory irritation, and may be harmful if ingested or inhaled. Proper personal protective equipment (PPE), including gloves, goggles, and lab coats, should be worn when handling the compound. It should be stored in a cool, dry place, away from incompatible substances such as strong bases or oxidizing agents. In case of a spill, the area should be ventilated, and the spill should be cleaned up using appropriate absorbent materials.
7. Environmental Impact
The environmental impact of 4-Nitrobenzyl Bromide is an important consideration, especially in its disposal. The compound is potentially hazardous to aquatic life and should not be released into the environment. Waste containing 4-Nitrobenzyl Bromide should be disposed of according to local regulations, typically through incineration in a chemical waste facility. Environmental precautions should be taken to prevent contamination of water sources and soil.
8. Safety Data
Hazard Classifications
- Irritant: Causes skin and eye irritation.
- Toxic: Harmful if inhaled or ingested.
Pictograms
- Exclamation Mark (Irritant)
Hazard Statements
- H315: Causes skin irritation.
- H319: Causes serious eye irritation.
- H335: May cause respiratory irritation.
- H411: Toxic to aquatic life with long-lasting effects.
Precautionary Statements:
- P261: Avoid breathing dust/fume/gas/mist/vapors/spray.
- P280: Wear protective gloves/protective clothing/eye protection/face protection.
- P305+P351+P338: If in eyes, rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do so. Continue rinsing.
- P301+P312: If swallowed, call a POISON CENTER or doctor/physician if you feel unwell.
9. Research and Studies
Recent research on 4-Nitrobenzyl Bromide has focused on its role as a versatile protecting group in organic synthesis and its application in the development of new pharmaceutical agents. Studies have explored its utility in the synthesis of complex molecules, including potential drug candidates and advanced materials. Additionally, research into its reactivity has led to the discovery of new synthetic methodologies that exploit the unique properties of this compound.
10. Conclusion
4-Nitrobenzyl Bromide is a highly valuable compound in organic synthesis, with significant applications in pharmaceuticals, material science, and chemical research. Its unique chemical properties, including its reactivity and ability to serve as a protecting group, make it an essential tool for chemists. By understanding its properties, applications, and safety considerations, researchers can effectively utilize 4-Nitrobenzyl Bromide in their work, contributing to advances in various scientific and industrial fields.
Releted Blog
FAQ
p-Nitrobenzyl bromide has been used as a reagent for the identification of many acids1 and phenols2 by conversion into their p-nitrobenzyl esters and ethers.
4-Nitrobenzyl bromide (CAS 100-11-8)
3,4-Dimethoxybenzyl bromide is an organic compound that is used in the synthesis of isoquinoline alkaloids.
romide can cause drowsiness, depresses the central nervous system, and can cause poisoning if taken in high doses or bromism (bromide intoxication) if taken very regularly in excessive doses.
