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Description
TCI D4776 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl Chloride is a heterocyclic building block in the form of an acid chloride that combines a substituted isoxazole core with a dichlorinated phenyl ring. The compound is recognised as a key intermediate in the synthesis of isoxazolyl penicillin antibiotics, for example the dicloxacillin group, because its acyl chloride group reacts readily and directly with the amine group of the beta-lactam nucleus. In an organic synthesis laboratory, its role is to present a complete isoxazole framework so that researchers can move straight into the coupling stage without having to construct the heterocyclic ring from the beginning.
The properties that make this material a preferred choice begin with the high reactivity of the carbonyl chloride group towards nucleophiles such as amines, alcohols and thiols, which allows amide and ester formation to proceed rapidly at mild temperatures with the help of an acid-scavenging base. The isoxazole ring contributes structural rigidity and a characteristic electronic profile that is useful in drug molecule design, while the two chlorine atoms at the 2 and 6 positions of the phenyl ring create directed steric hindrance and an electronic influence that improves the resistance of the resulting products. Together, these features give chemists a reliable and predictable acylating partner.
In Indonesian laboratories, this building block is typically used in pharmaceutical and medicinal chemistry research groups, in university organic synthesis laboratories, and in development units working on beta-lactam antibiotic derivatives. It suits work carried out at bench scale, where a ready-made isoxazole framework shortens a synthetic route and reduces the number of preparative steps. Analytical and formulation teams also draw on it when preparing reference derivatives, and teaching laboratories use it to demonstrate acid chloride chemistry in a practical, application-linked context.
Laboratory Applications
- Isoxazolyl penicillin synthesis: the acyl chloride group couples directly with the amine of the beta-lactam nucleus, giving a short and efficient route to antibiotics of the dicloxacillin group.
- Amide bond formation: high reactivity towards primary and secondary amines allows rapid acylation at mild temperatures when an acid-scavenging base is present in the reaction mixture.
- Ester preparation: alcohols react readily with the carbonyl chloride function, so researchers can build ester derivatives of the isoxazole scaffold without additional coupling reagents or activation steps.
- Thioester and thiol derivatisation: thiols are among the nucleophiles this acid chloride accepts, opening access to sulfur-containing analogues of the dichlorophenyl isoxazole framework for structure studies.
- Medicinal chemistry scaffold work: the rigid isoxazole ring and the directed steric hindrance from the 2,6-dichloro substitution make it valuable for designing drug molecules with defined geometry.
Specifications
- Brand: TCI
- CAS number: 4462-55-9
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Product code: D4776
- Chemical class: heterocyclic building block, acid chloride (carbonyl chloride)
- Pack sizes: available in standard TCI research pack sizes; please confirm the current options when ordering
- Storage: keep tightly closed in a cool, dry place, protected from moisture
Handling and Storage
Store the container tightly closed in a cool, dry and well-ventilated place, away from moisture, since acid chlorides hydrolyse on contact with water or humid air and release hydrogen chloride. Keep the material in its original tightly sealed glass container, and reseal promptly after each use; where practical, handle and weigh under dry inert gas. Work in a fume hood and wear chemical-resistant gloves, safety goggles and a laboratory coat, because the compound is corrosive and its vapours irritate the eyes and respiratory tract. Keep it separated from water, alcohols, amines, bases and oxidising agents, and use dry glassware and dry solvents throughout. Dispose of residues and rinses as chemical waste following institutional procedures, and consult the manufacturer's safety data sheet before first use.
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