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Description
TCI D2647 2,3-Dibromo-3-phenylpropionic Acid, bearing CAS number 6286-30-2, is a three-carbon carboxylic acid that carries two neighbouring bromine atoms together with a phenyl group at the end of the chain. The compound belongs to the family of non-heterocyclic building blocks and, structurally, represents the product of bromine addition across the double bond of cinnamic acid. In the laboratory it serves as a versatile intermediate because it presents three reactive points at once: a carboxyl group that can be esterified or amidated, and two bromine atoms that are ready to undergo substitution or elimination depending on the reaction conditions the researcher selects.
The property that makes this material widely used is the ease with which double elimination can be performed. Under suitable basic treatment, both bromine atoms can be removed together with one proton to form a triple bond, which makes the compound a practical route towards phenylpropiolic acid derivatives and phenyl-substituted terminal alkynes without the need for expensive reagents. When only a single elimination step is desired, the vinyl bromide product that forms still retains one bromine atom as a cross-coupling handle. The presence of bromine atoms at adjacent positions also creates stereogenic centres, giving synthetic chemists control over the geometry of the products they obtain.
In Indonesian laboratories, this building block is typically encountered in university and institutional research groups working on organic synthesis, in postgraduate research on the preparation of alkyne and cinnamate derivatives, and in methodology studies that explore elimination and coupling reactions. It is generally used at bench scale in fume-hooded synthesis laboratories, where researchers weigh out the solid, run the reaction under controlled basic or coupling conditions, and characterise the resulting intermediates before carrying them forward into longer synthetic sequences.
Laboratory Applications
- Synthesis of phenylpropiolic acid derivatives: double dehydrohalogenation under basic conditions removes both bromine atoms and a proton, delivering the alkyne acid framework directly without recourse to expensive specialist reagents.
- Preparation of phenyl-substituted terminal alkynes: the same double elimination pathway provides a straightforward and economical entry to arylalkyne scaffolds that are otherwise prepared through more elaborate multi-step routes.
- Vinyl bromide intermediate generation: stopping at a single elimination step yields an alkenyl bromide that retains one bromine atom, ready to serve as a handle in subsequent cross-coupling chemistry.
- Carboxyl group derivatisation studies: the free carboxylic acid can be esterified or amidated, allowing researchers to build ester and amide libraries while leaving the dibromide portion intact for later transformation.
- Stereochemistry and reaction methodology teaching or research: the adjacent bromine atoms create stereogenic centres, making this compound useful for investigating stereocontrol in elimination, substitution and coupling reactions.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS Number: 6286-30-2
- Catalogue Code: D2647
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack Sizes: available in standard TCI catalogue pack sizes; please confirm the required quantity when ordering
- Storage: keep in a tightly closed original container, in a cool, dry and well-ventilated place away from incompatible materials
Handling and Storage
Store the material in its original, tightly closed container in a cool, dry and well-ventilated area, protected from direct sunlight, moisture and heat sources, and kept away from strong bases and strong oxidising agents. Use only chemically compatible containers with secure closures, and reseal immediately after each use to prevent moisture uptake and contamination of the remaining stock. All weighing and transfer operations should be carried out inside a fume hood using appropriate personal protective equipment, including safety goggles, chemically resistant gloves and a laboratory coat. As an organobromine compound, it should be handled with care to avoid skin contact, eye contact and inhalation of dust. Dispose of residues and contaminated materials as halogenated chemical waste in accordance with institutional and local regulations, and always consult the manufacturer's safety data sheet before use.
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