Bromoacetonitrile: An Overview
Bromoacetonitrile is an organobromine compound with the chemical formula C₂H₂BrN. It is a volatile and reactive chemical that plays an important role as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals.
Chemical Structure and Properties
Chemical Name: Bromoacetonitrile
Molecular Formula: C₂H₂BrN
Molecular Weight: 118.95 g/mol
CAS Number: 590-17-0
Physical Properties:
Bromoacetonitrile consists of a bromo group (-Br) attached to a carbon atom, which is also part of a nitrile group (-CN). This simple two-carbon structure makes the compound highly reactive, especially due to the presence of the electron-withdrawing nitrile group and the electron-attracting bromine atom.
Synthesis
Bromoacetonitrile can be synthesized through the bromination of acetonitrile, usually involving bromine (Br₂) or a bromine source in the presence of catalysts. The reaction occurs at the methylene group (CH₂) adjacent to the nitrile, introducing a bromine atom into the molecule.
Applications
Bromoacetonitrile is an organobromine compound with the chemical formula C₂H₂BrN. It is a volatile and reactive chemical that plays an important role as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals.
Chemical Structure and Properties
Chemical Name: Bromoacetonitrile
Molecular Formula: C₂H₂BrN
Molecular Weight: 118.95 g/mol
CAS Number: 590-17-0
Physical Properties:
| Property | Description |
|---|---|
| Appearance | Colorless to pale yellow liquid |
| Melting Point | -58°C |
| Boiling Point | 102-104°C |
| Density | 1.616 g/cm³ |
| Solubility in Water | Reacts with water |
| Solubility in Organic Solvents | Soluble in solvents like ethanol, ether, and acetone |
Synthesis
Bromoacetonitrile can be synthesized through the bromination of acetonitrile, usually involving bromine (Br₂) or a bromine source in the presence of catalysts. The reaction occurs at the methylene group (CH₂) adjacent to the nitrile, introducing a bromine atom into the molecule.
Applications
- Pharmaceutical Industry:
Bromoacetonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. It provides a reactive platform that can undergo further chemical transformations to introduce more complex molecular structures in drug development. For instance, it can be used in alkylation reactions or to introduce nitrile functionalities into drug candidates. - Agrochemicals:
In the agrochemical industry, bromoacetonitrile is employed in the synthesis of herbicides, fungicides, and pesticides. The reactivity of the nitrile and bromine groups makes it a valuable precursor for creating bioactive molecules that can protect crops from pests and diseases. - Organic Synthesis:
Bromoacetonitrile serves as a versatile reagent in organic synthesis. Its dual functional groups (bromo and nitrile) enable it to participate in various chemical reactions, including nucleophilic substitution and addition reactions. It can be used to introduce nitriles or bromoalkyl groups into organic molecules. - Polymer Chemistry:
Bromoacetonitrile can also be used in the functionalization of polymers, introducing reactive groups for further modification. It allows for the incorporation of nitrile groups into polymer backbones, which can be used to modify the physical properties of the material.