Ethyl S-4-chloro-3-hydroxybutyrate
[CAS# 86728-85-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl S-4-chloro-3-hydroxybutyrate
• Synonyms: Ethyl (S)-(-)-4-chloro-3-hydroxybutyrate
• Molecular Formula: C₆H₁₁ClO₃
• Molecular Weight: 166.60
• CAS Registry Number: 86728-85-0
• EC Number: 617-912-5
• SMILES: CCOC(=O)C[C@@H](CCl)O

Properties

• Density: 1.19
• Boiling point: 93-95 °C (5 mmHg)
• Refractive index: 1.4515-1.4535
• Flash point: 109 °C
• alpha: -14.5 ° (c=neat)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P354+P338-P317-P321-P330-P332+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Ethyl S-4-chloro-3-hydroxybutyrate is prepared by condensation of an ethyl ester with chloroacetic acid followed by hydroxylation under controlled conditions. This synthesis produces a clear, colorless liquid with a specific molecular structure characterized by a chlorobutyrate moiety with a hydroxyl group at the third carbon position. From a chemical point of view, ethyl S-4-chloro-3-hydroxybutyrate is characterized by the presence of an ester functional group (-COOEt), a chlorinated carbon (-CH2Cl), and a hydroxyl group (-OH) on the butyrate backbone. These structural elements give it unique physical and chemical properties, including solubility in organic solvents, stability under mild conditions, and reactivity suitable for a wide range of organic transformations.

This compound is a key intermediate in the synthesis of pharmaceutical compounds, especially those targeting metabolic disorders and neurological diseases. Its structural modification potential can be used to develop prodrugs and analogs with enhanced bioavailability and therapeutic effects.

Ethyl S-4-chloro-3-hydroxybutyrate can be used as a key intermediate in the production of fine chemicals and specialty compounds. Its incorporation into chemical synthesis pathways can enhance product functionality and facilitate the synthesis of complex organic molecules.

The biochemical properties of this compound make it valuable in biomedical research, including enzyme kinetic studies and biochemical pathway studies. Its selective interactions with biological targets aid in understanding cellular processes and disease mechanisms.

Ongoing research programs focus on exploring the potential of ethyl S-4-chloro-3-hydroxybutyrate in: studying its role in drug delivery systems, such as liposomal formulations and nanocarriers to improve drug stability and targeted delivery to specific tissues; exploring its catalytic properties in organic reactions, aiming to improve reaction efficiency and selectivity in industrial processes; evaluating its environmental impact and exploring sustainable synthetic pathways to minimize waste and promote environmentally friendly manufacturing practices.

Research on the safety and regulatory compliance of ethyl S-4-chloro-3-hydroxybutyrate ensures its safe handling and use in industrial applications. The regulatory framework involves environmental impact assessments, occupational health guidelines, and product stewardship to mitigate potential risks associated with its manufacture and use.

References

2021. Biocatalytic approaches for the synthesis of optically pure vic-halohydrins. Applied Microbiology and Biotechnology, 105(8).
DOI: 10.1007/s00253-021-11266-2

2019. Stereoselective synthesis of optical isomers of ethyl 4-chloro-3-hydroxybutyrate in a microfluidic chip reactor. Journal of Flow Chemistry, 9(3).
DOI: 10.1007/s41981-019-00043-y

2017. Enhancing the biocatalytic manufacture of the key intermediate of atorvastatin by focused directed evolution of halohydrin dehalogenase. Scientific Reports, 7.
DOI: 10.1038/srep42064