Tert-Butyl Bromoacetate: Chemical Insights and Industrial Realities

What Is Tert-Butyl Bromoacetate?

Tert-Butyl Bromoacetate comes up in chemical labs across the globe. Known by its molecular formula C6H11BrO2, this compound brings together a tert-butyl group with a bromoacetate core, making it stand out as a useful alkylating agent. The HS Code for Tert-Butyl Bromoacetate, usually 2915.90.9000, distinguishes it in trade databases, helping customs and importers identify its regulated nature. From a materials point of view, its molecular weight clocks in at roughly 195.06 g/mol. Researchers who come into contact with this chemical see it most as a colorless to light yellow liquid at room temperature. The appearance might trick new hands who expect a solid or powder, but the liquid phase and the slight, sharp odor clear any confusion once the seal breaks.

Physical Properties and Observations

Tert-Butyl Bromoacetate attracts attention for specific reasons. The density sits at about 1.26 g/cm³. Pouring a sample reveals a clear, almost oily-looking liquid, with some batches showing faint crystals or flakes if the storage temperature drops. Unlike simple organic solvents, this compound does not evaporate rapidly, and you notice the viscous drag on glassware. The boiling point generally measures around 62–64 °C at 15 mmHg, with a melting point below typical room temperatures, confirming that solid or powder forms rarely appear unless chilled or isolated carefully. I once spilled a few milliliters on a benchtop during cleanup and observed its residue tending towards a sticky, crystalline smear if it sits exposed—unmistakable for any other common chemical.

Chemical Structure and Reactivity

The backbone, a tert-butyl ester attached to a reactive bromoacetate group, comes with some chemistry baggage. Lab work often turns to this molecule for its reliability as a halogen alkylating agent in organic synthesis. The bromo group, sticking out from the electron-withdrawing acetate, allows efficient nucleophilic substitution, making it particularly useful for introducing tert-butyl ester protecting groups. I’ve seen graduate students eagerly reach for bottles of Tert-Butyl Bromoacetate to modify amino acids, peptides, or advanced intermediates during multi-step syntheses. They count on its purity, structure, and high reactivity—attributes rooted in the stability and electron balance of its functional groups.

Applications and Industry Impact

Peptide synthesis teams rely on this chemical for protecting carboxyl groups. Medicinal chemistry divisions often prefer tert-butyl derivatives over methyl due to the ease of removing the protecting group after crucial coupling reactions. The material flows freely within synthetic chemistry pipelines, helping to shape pharmaceutical intermediates for both research and commercial-scale drug development. My time collaborating with manufacturing chemists offered clarity—this chemical, found in 1-liter or 5-liter containers shipped with special liners, comes consistently checked for purity of at least 98%. Analytical data—such as IR, NMR, and GC-MS—serves as a secondary guarantee. These measures are non-negotiable because even slight impurities derail downstream reactions, costing companies both time and money.

Safety, Hazards, and Storage

Tert-Butyl Bromoacetate cannot be handled lightly. The bromo functional group, coupled with the ester, sets off several hazard bells. Prolonged skin contact brings a severe, burning irritation, and inhaling its vapors irritates respiratory pathways. Safety data sheets carry clear warnings: wear gloves and goggles, use in a chemical fume hood, and avoid any ingestion or direct inhalation under any circumstances. I keep the waste stream segregated and double-check the fume hood sash height specifically when weighing or transferring this material. Even a single drop, left on an unprotected forearm, can trigger redness that lingers for days. Fire and chemical reactivity risk remain low under standard laboratory conditions, yet the bromine content brings heightened environmental harm. Waste must be dealt with through licensed chemical wastewater contractors because direct disposal risks local water systems. Proper storage demands cool, dry places—UV, moisture, and exposure to air cause breakdown and hazardous fume generation. In long-term use, amber or opaque containers shielded from direct sunlight extend shelf life and safeguard anyone working nearby.

Quality, Form, and Raw Material Sourcing

Form dictates handling and application routes. Though most shipments arrive in liquid form, some specialized orders provide the compound as flakes, pearls, or crystals—usually to simplify dosing in automated synthesis systems. Experienced chemists recognize that form consistency makes a crucial difference during scale-up: a liquid allows for continuous pumping in manufacturing plants, while solid forms get portioned by weight for small-scale or batch reactions. Genuine quality assurance starts at the sourcing stage. Raw material checks must confirm both identity and absence of cross-contaminants. Fluctuations in density, purity measurements, or crystal structure point towards possible issues in synthesis or storage—factors that demand immediate resolution. As regulations tighten, auditors visit suppliers periodically, inspect production logs, and collect analytical samples to ensure the product meets regulatory requirements from both environmental and worker-safety perspectives.

Risks, Harm, and the Push Toward Safer Solutions

Historical trends show why attention to safe handling and sustainability stays front and center. Past accidents with organic bromides regularly made the news—spills that sickened lab staff, pipeline leaks affecting downstream aquifers, or storage tank mishaps leading to fire hazards. Stories from older colleagues about rough safety standards in the 1980s reinforce just how far the industry has come. Current protocols, shaped by regulatory bodies and real-world lessons, set a zero-tolerance policy for exposure and waste mishandling. Engineering controls, written documentation, and digitized safety logs accompany every transaction, giving oversight into how much, where, and by whom the material gets used. Ongoing advances in synthetic route design encourage swapping harmful alkylating agents for greener counterparts wherever possible. Peer-reviewed studies now highlight reagents or alternative protecting groups with similar performance but lower environmental or human health impacts. Companies that publicly disclose their safety metrics and introduce research initiatives focused on “green chemistry” earn trust, retain business, and manage risk while contributing toward broader, positive change within the industry.