Methyl bromoacetate
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Category：Chemical Additives Own Brand：MT /MOQ:100KG /From China/ B2B only.
Introduction
Methyl bromoacetate is an organic compound with the chemical formula C₃H₅BrO₂. It consists of a bromoacetate group (BrCH₂COO-) attached to a methyl group (-CH₃). This structure makes it an ester of bromoacetic acid and methanol, belonging to the class of halogenated esters.
Methyl bromoacetate is widely used as a reagent in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. It is valued for its ability to introduce the bromoacetyl group into target molecules, which is useful in the synthesis of complex organic compounds. It is also employed in the modification of peptides and other biomolecules, as well as in the production of dyes and fragrances.
The compound is typically a clear, colorless to pale yellow liquid with a pungent odor. It is highly reactive, moisture-sensitive, and can cause severe irritation to the skin, eyes, and respiratory system. Proper handling, including the use of personal protective equipment (PPE) and working in a fume hood, is essential. It should be stored in a cool, dry place, away from moisture and incompatible materials.
| Category | Details |
|---|---|
| Chemical Name | Methyl bromoacetate (MBrA) |
| Molecular Formula | C₃H₅BrO₂ |
| CAS Number | 96-32-2 |
| Appearance | Colorless to pale yellow liquid |
| Odor | Pungent, irritating |
Physical & Chemical Properties
| Property | Value/Description |
|---|---|
| Boiling Point | 143–145°C (289–293°F) |
| Melting Point | −50°C (−58°F) |
| Density | 1.655 g/cm³ (20°C) |
| Solubility | Miscible with organic solvents (ethanol, ether); insoluble in water |
| Flash Point | 47°C (117°F) – Flammable |
| Vapor Pressure | 4.5 mmHg (20°C) |
Production Methods
| Method | Process Description |
|---|---|
| Esterification | Bromoacetic acid + Methanol (acid-catalyzed, e.g., H₂SO₄) |
| Halogenation | Methyl acetate + Bromine (under UV light or catalyst) |
Applications
| Industry | Uses |
|---|---|
| Chemical Synthesis | Alkylating agent for pharmaceuticals, agrochemicals |
| Pharmaceuticals | Intermediate for antibiotics, antimalarials |
| Agrochemicals | Precursor for herbicides, pesticides |
| Peptide Chemistry | Reagent for carboxyl group activation |
Safety & Toxicity
| Parameter | Value/Recommendation |
|---|---|
| OSHA Exposure Limit | Not established (handle with extreme caution) |
| Health Hazards | Corrosive; causes severe skin/eye burns, respiratory irritation |
| Environmental Impact | Toxic to aquatic life; avoid release into water |
| Handling | Use PPE (gloves, goggles, fume hood); store in cool, ventilated area |
Comparison with Related Esters
| Ester | Methyl Bromoacetate vs. Alternatives |
|---|---|
| Methyl chloroacetate | Less reactive but more toxic |
| Ethyl bromoacetate | Higher boiling point, slower reaction kinetics |
| Methyl iodoacetate | More reactive but less stable |
Summary
Methyl bromoacetate is a highly reactive alkylating ester used in pharmaceuticals, agrochemicals, and peptide synthesis. Its corrosive nature and toxicity demand strict safety measures. Despite hazards, it remains valuable in organic synthesis due to its versatility. Research focuses on safer handling protocols and greener alternatives.
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