Organic chemistry relies on a variety of small but highly reactive molecules to build complex compounds. Among these, bromoacetonitrile stands out as a valuable synthetic intermediate. Known for its reactive nature and simple structure, bromoacetonitrile plays a significant role in pharmaceutical research, agrochemical development, and academic studies.
This blog explores what bromoacetonitrile is, its chemical properties, common applications, and safety considerations, offering a comprehensive overview for students, researchers, and professionals working in the chemical sciences.
What Is Bromoacetonitrile?
The halogenated nitrile chemical bromoacetonitrile has the molecular formula C2H2BrN. It consists of a bromine atom and a nitrile group (–C≡N) attached to a two-carbon backbone. This small but highly reactive molecule is known for its ability to participate in a wide range of organic transformations.
Basic Information:
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Chemical Name: Bromoacetonitrile
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Molecular Formula: C₂H₂BrN
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Molecular Weight: 120.95 g/mol
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CAS Number: 590-17-0
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Appearance: Clear to pale yellow liquid
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Odor: Pungent, irritating
Chemical Structure and Properties
In chemical synthesis, bromoacetonitrile’s structure is straightforward but efficient. It has a nitrile group (-C≡N) that is directly linked to a bromomethyl group (-CH₂Br). This combination gives the compound both electrophilic and nucleophilic reactivity, making it a useful intermediate.
Key Properties:
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Boiling Point: Approximately 108°C
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Solubility: Water-soluble to a slight extent; soluble in the majority of organic solvents
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Reactivity: Because it contains both nitrile and bromine functional groups, it is extremely reactive.
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Stability: Stable under recommended storage conditions but should be handled carefully due to its toxic and volatile nature
The dual functional groups allow bromoacetonitrile to undergo a variety of reactions, such as nucleophilic substitution, condensation, and cyclization.
Applications of Bromoacetonitrile
Bromoacetonitrile is used in a number of specialized chemical applications. Its reactivity allows it to serve as a building block in the preparation of more complex molecules.
1. Pharmaceutical Synthesis
Bromoacetonitrile is commonly used in the preparation of heterocyclic compounds, which are a core structure in many pharmaceutical drugs. Its ability to react with amines, alcohols, and other nucleophiles makes it valuable in early-stage drug discovery and medicinal chemistry.
2. Agrochemical Research
In agrochemical development, bromoacetonitrile serves as a precursor for compounds with fungicidal, herbicidal, or pesticidal properties. It is used to create biologically active molecules that help protect crops from pests and diseases.
3. Intermediate in Organic Reactions
Due to its structure, bromoacetonitrile is used as a key intermediate in various laboratory-scale reactions. It is particularly useful in the synthesis of nitriles, amides, and imines. In many reactions, it introduces a cyanoethyl group or acts as a linker between molecular fragments.
4. Polymer Chemistry
Though less common, bromoacetonitrile can also be used in modifying polymer backbones by introducing reactive groups for cross-linking or functionalization, especially in research applications.
Handling and Safety Precautions
Bromoacetonitrile is toxic and potentially hazardous, and it should be handled with caution in well-controlled laboratory environments. It can release toxic fumes if heated or exposed to moisture and may be harmful if inhaled or absorbed through the skin.
Safety Guidelines:
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Always handle in a well-ventilated fume hood.
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Use appropriate personal protective equipment (PPE) including gloves, goggles, and lab coats.
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Store in tightly sealed containers in a cool, dry, and well-ventilated area, away from incompatible substances such as strong oxidizing agents and bases.
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Avoid direct contact with skin or eyes. In case of exposure, seek immediate medical attention.
First Aid:
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Inhalation: Move to fresh air and seek medical help.
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Skin contact: Wash with plenty of water and remove contaminated clothing.
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Eye contact: Rinse thoroughly with water for at least 15 minutes and get medical attention.
Always consult the Material Safety Data Sheet (MSDS) before working with bromoacetonitrile.
Environmental Considerations
Bromoacetonitrile is not readily biodegradable and can pose environmental risks if not properly managed. Laboratories and industrial facilities must follow regulatory guidelines for the safe disposal of bromoacetonitrile and its byproducts. Waste should be collected in labeled hazardous chemical containers and disposed of through certified chemical waste handlers. Methyl carbazate is commonly used as a key intermediate in the synthesis of heterocyclic compounds.
Conclusion
Bromoacetonitrile is a versatile and valuable compound in the realm of organic synthesis. Its dual functionality, combining a bromine atom with a nitrile group, allows it to participate in a wide range of chemical reactions. Whether used in pharmaceutical research, agrochemical development, or material science, bromoacetonitrile offers strong utility as an intermediate.
However, its reactivity and toxicity demand careful handling and strict adherence to safety protocols. When used responsibly, bromoacetonitrile can significantly aid chemists in developing new compounds and advancing scientific knowledge.
