Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate, CAS No. 90866-33-4

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90866-33-4

Catalog No. EBD47629

CAS 90866-33-4

Name Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate

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Basic Information

Synonyms: 4-Chloro-3-hydroxybutyricacidethylester Ethyl(R)-(+)-4-chloro-3-hydroxybutyrate (R)-(+)-ethyl-4-chloro-3-hydroxybutanoate (R)-(+)-4-Chloro-3-hydroxybutyricacidethylester R(+)-Ethyl-4-Chloro-3-Hydroxybutanoate (R)-4-chloro-3-hydroxybutyricacidethylester (R)-4-Chloro-3-hydroxybutanoicacidethylester Ethyl(R)-4-chloro-3-hydroxybutyrate Ethyl(R)-4-chloro-3-Hydroxybutanoate Ethyl(R)-(+)-4-chloro-3-Hydroxybutanoate butanoicacid,4-chloro-3-hydroxy-,EthylESTER,(R) (R)-(+)-Ethyl-4-chloro-3-hydroxybutyrate rechb (r)-(+)-ethyl-4-chloro3-hydroxybutanoate (R)-4

Molecular Formula: C6H11ClO3

Molecular Weight: 166.6

MDL Number: MFCD00211242

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Halogenated Compounds

Product Description:

Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate is a chiral building block characterized by its (R)-configuration at the stereogenic center. It is a colorless to pale yellow liquid with the molecular formula C6H11ClO3. This compound is a key synthon due to the presence of both a reactive chloro group and a protected hydroxyl group (as an ester), which can be further manipulated in synthetic sequences. Its primary and most significant application is as a crucial chiral intermediate in the synthesis of various pharmaceuticals. Most notably, it serves as a key precursor in the industrial production of the cholesterol-lowering drug Atorvastatin (Lipitor) and other HMG-CoA reductase inhibitors (statins). The (R)-enantiomer is specifically required for constructing the biologically active side chain of these molecules. The compound is also used in the synthesis of L-carnitine and other bioactive compounds. The synthesis and use of this high-purity chiral intermediate are of great importance in asymmetric synthesis and pharmaceutical process chemistry. It is typically handled with care, as it is a halogenated compound and may cause skin and eye irritation.

Physical Properties

Melting Point: 93-95 °C

Boiling Point: 93-95 °C/5 mmHg(lit.)

Flash Point: 113 °C

Density: 1.19 g/mL at 25 °C(lit.)

Refractivity: n20/D 1.453(lit.)

Analytical Data

Appearance: Colorless to light yellow liquid