2-Bromobutyric acid #CAS80-58-0

2-Bromobutyric acid #CAS80-58-0

Colorless, clear or slightly yellow oily liquid. Melting point -4°C, boiling point 181–182°C (33.25 kPa), 127–128°C (3.33 kPa, Chemicalbook), 107°C (1.6 kPa). Relative density 1.5669 (20/20°C). Soluble in alcohol and ether, soluble in 15 parts water. Refractive index 1.4720.

It is a dual-functional aliphatic saturated halogenated acid that combines the properties of carboxylic acids and α-position active halogens. In terms of chemical properties, due to the bromine atom in the structure being located at the α-position of the carbonyl group, it is strongly influenced by the electron-withdrawing effect of the carbonyl group. The α-carbon-bromine bond is extremely prone to nucleophilic substitution reactions. Under the action of mild bases or nucleophilic reagents (such as amines, sodium alcohols, thioalcohols, cyanides), it can efficiently be converted into corresponding high-value-added derivatives such as α-amino butyric acid, α-hydroxybutyric acid, or α-cyanobutyric acid; meanwhile, it retains the typical activity of aliphatic carboxylic acids. Its carboxyl group can form salts with bases, undergo esterification reactions with alcohols (forming 2-bromobutyrate), or react with dicyclo-sulfoxide to convert into highly reactive 2-bromobutyldichloro chloride. Moreover, this compound belongs to a strong organic acid and has strong corrosiveness and hygroscopicity. In alkaline aqueous solutions, it is prone to hydrolyze bromine easily when heated, or undergo intramolecular elimination and dehydrogenation of hydrogen bromide (HBr) reaction at high temperatures. Daily storage requires sealing in a cool, dry, moisture-proof environment, and must be strictly avoided from contact with strong bases and strong oxidants.

Application Of 2-Bromobutyric acid

2-Bromobutyric acid was used in the synthesis of S-(1-carboxypropyl)-L-cysteine.

Organic synthesis intermediates. Used in organic synthesis, also as colorant intermediates, and used as intermediates for pesticides and medicines.

In industry, it is mainly used as an efficient and key core component for synthesizing pharmaceutical intermediates, agricultural fine chemicals and special fine chemicals. In the pharmaceutical industry, it relies on its dual reactive properties of the active α-carbon bromo bond and the acylated carboxyl group, and is widely used on a large scale to construct the core frameworks of chiral and non-chiral drugs. It is the core starting material for industrial synthesis of broad-spectrum antiepileptic drugs, cerebrovascular dilators, and various non-steroidal anti-inflammatory drugs. In the pesticide manufacturing field, it is often used to synthesize nitrogen- or oxygen-containing heterocyclic fatty acid derivatives with high bactericidal or herbicidal activity, in order to enhance the targeted biological activity of pesticides. Moreover, due to its ability to be efficiently converted into non-natural amino acid monomers such as α-amino butyric acid through nucleophilic substitution reactions, it is also widely applied in the modification and research process of special high-molecular surfactants, liquid crystal material modifiers, and biochemical functional additives in industry.

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