Methyl 2-Bromooctanoate: Comprehensive Description and Commentary

What is Methyl 2-Bromooctanoate?

Methyl 2-Bromooctanoate serves a clear purpose in organic synthesis. It belongs to the family of bromoalkanoate esters, structured as a methyl ester attached to an eight-carbon chain, with a single bromine atom bonded at the second carbon. This setup brings a certain reactivity and value to tasks that involve forming new carbon-carbon or carbon-heteroatom bonds, especially for introducing a brominated aliphatic segment in specialty chemicals or pharmaceuticals. Many chemists who work with building-block molecules appreciate how methyl esters like this one help when precision and sequential reactions matter. Its typical applications reach from agrochemical intermediates to surfactant synthesis, reflecting not only the reactivity of the bromide but also the relative non-volatility expected for an octanoate derivative.

Structure and Molecular Details

Molecular formula stands at C9H17BrO2, indicating a straight octane backbone with a methyl ester at the terminal and a bromine at position two. Its molar mass comes in at about 237.13 g/mol, a figure that guides both logistical planning and hazard analysis. Looking at the structural formula tells a lot: the carboxyl group’s methylation reduces its polarity compared to an acid, while the two-position bromination enhances the molecule’s reactivity and potential for selective displacement reactions. On a practical note, the bromine’s large atomic size shifts electron density, which many organic chemists use when seeking regioselectivity, especially in the production of chiral molecules using asymmetric synthesis.

Physical Properties

Methyl 2-Bromooctanoate appears as a colorless to light-yellow liquid under standard conditions, sometimes presenting as a slightly oily solid as storage temperatures drop toward ambient levels. Specific density ranges from 1.13 to 1.17 g/cm³, a value higher than water, thanks to the contribution of both the bromine atom and the long hydrocarbon chain. Its solubility leans toward organic solvents—ethyl acetate, acetone, and chloroform feature as frequent choices—while water solubility remains negligible. Boiling point commonly falls around 120-130°C at reduced pressure, considering the methyl ester functional group’s volatility and the heavy bromine slowing down vaporization. Handling the raw material in daily laboratory or plant settings also means taking note of its moderate viscosity. Sometimes it comes in the form of thick liquid, other times as small flakes or even pearls, depending on storage, though crystal forms rarely show up outside carefully controlled crystallization protocols.

Chemical Properties and Safety Issues

A key feature of methyl 2-bromooctanoate centers on its dual reactivity. The ester group stays mostly stable under mild conditions, but saponification with aqueous base yields 2-bromooctanoic acid, while the bromine atom reacts lively under nucleophilic substitution with amines, thiols, or other nucleophiles. This makes the compound a frequent intermediate in pharmaceutical and agrochemical synthesis. Risks come in from both the ester and bromide moieties. Direct contact can irritate skin and mucous membranes; inhalation of vapor or extended exposure brings headaches and nausea—one more example of why fume hoods and gloves count in real-world handling. Chronic exposure or mishandling brings concern for organ toxicity. Combustion generates corrosive and toxic gases, including hydrogen bromide, so proper ventilation and Class B fire extinguishing agents should always stay close during operations.

Material Forms and Handling

Lab shipments and industrial drums both often carry methyl 2-bromooctanoate as a stabilized liquid in amber bottles or steel-lined plastic containers, kept away from direct light and moisture. In the rare cases where crystal or powdered forms appear, they tend to cluster during recrystallization—a reminder to chemists of the need for careful control of cooling rates and solvent systems. Contamination risk exists both from moisture ingress, leading to hydrolysis, and from dust, making sealed transfer lines or nitrogen-purged systems routine in bulk storage. Disposal policies focus on high-temperature incineration in facilities equipped for halogenated waste. Emergency eye washes and spill kits are must-haves in any facility storing liters or more of this raw material.

HS Code, Regulatory, and Supply Information

Methyl 2-bromooctanoate falls under HS Code 2915.90, tying it to acyclic carboxylic acids and their derivatives classified for customs and shipping. International transport requires documentation regarding hazard class and UN numbers associated with both flammable and toxic organic chemicals. Suppliers list the product as either a lab reagent or a fine chemical intermediate. Regulations on import and transport vary: the United States and REACH-compliant Europe both require SDS documentation and reporting for quantities exceeding certain thresholds. Facilities planning new procurement rounds must coordinate shipping schedules and customs clearances to minimize storage time, reduce risk, and guarantee batch quality.

Hazards and Solutions in Workplace Settings

In most professional laboratories and plants, the top risk involves accidental skin or eye exposure and spill-related inhalation of vapor. A single missed glove change or lapse in use of goggles can mean discomfort or injury. Proper PPE habits, backed by clear training for all employees, cut accident rates. Chemical-resistant gloves, splash-proof goggles, and dedicated fume extraction hoods or booths have become standard. I’ve seen firsthand how setting up clear spill protocols—such as absorbents, neutralizers, and immediate disposal—restores a sense of security after near-miss events. Ignoring disposal safety can lead to fires or toxic releases, so management oversight and maintenance of extinguishers and chemical spill kits pay off in everyday resilience. For organizations scaling up, consulting both regulatory advisors and environmental health specialists before expansion can prevent workplace injuries, regulatory fines, and unnecessary hazards.

Impact and Recommendations in Sourcing and Use

As demand for specialty intermediates continues, supply chain disruptions from regulatory changes or shipping bottlenecks pose a real headache. In practice, robust partnerships with vetted suppliers and routine quality checks limit surprises. Scanning for batch documentation, full Certificates of Analysis, and periodic impurity profiling makes a difference in keeping downstream synthesis on track. I find that companies with dedicated raw materials teams, trained not just in purchasing but in chemical engineering and risk assessment, handle procurement smoother and with fewer losses from spoilage or mishandling. Onsite chemical inventories can easily spiral out of control without quarterly audits and smart tracking systems. Achieving safe, reliable use calls for active collaboration between purchasing, EHS, and laboratory teams in any facility.