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Methyl bromoacetate

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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.

CategoryDetails
Chemical NameMethyl bromoacetate (MBrA)
Molecular FormulaC₃H₅BrO₂
CAS Number96-32-2
AppearanceColorless to pale yellow liquid
OdorPungent, irritating

Physical & Chemical Properties

PropertyValue/Description
Boiling Point143–145°C (289–293°F)
Melting Point−50°C (−58°F)
Density1.655 g/cm³ (20°C)
SolubilityMiscible with organic solvents (ethanol, ether); insoluble in water
Flash Point47°C (117°F) – Flammable
Vapor Pressure4.5 mmHg (20°C)

Production Methods

MethodProcess Description
EsterificationBromoacetic acid + Methanol (acid-catalyzed, e.g., H₂SO₄)
HalogenationMethyl acetate + Bromine (under UV light or catalyst)

Applications

IndustryUses
Chemical SynthesisAlkylating agent for pharmaceuticals, agrochemicals
PharmaceuticalsIntermediate for antibiotics, antimalarials
AgrochemicalsPrecursor for herbicides, pesticides
Peptide ChemistryReagent for carboxyl group activation

Safety & Toxicity

ParameterValue/Recommendation
OSHA Exposure LimitNot established (handle with extreme caution)
Health HazardsCorrosive; causes severe skin/eye burns, respiratory irritation
Environmental ImpactToxic to aquatic life; avoid release into water
HandlingUse PPE (gloves, goggles, fume hood); store in cool, ventilated area

Comparison with Related Esters

EsterMethyl Bromoacetate vs. Alternatives
Methyl chloroacetateLess reactive but more toxic
Ethyl bromoacetateHigher boiling point, slower reaction kinetics
Methyl iodoacetateMore 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.

Declaration: The products displayed on this website are intended exclusively for industrial applications or scientific research. They are not intended for medical, pharmaceutical, or food use. In accordance with applicable laws and regulations, purchasing organizations must hold valid qualifications and approvals.

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