4279-77-0

Basic information

• Product Name: MONOTHIOLPHENYL MALONATE
• Synonyms: MONOTHIOLPHENYL MALONATE;3-oxo-3-(phenylthio)propanoic acid;3-oxo-3-phenylsulfanylpropanoic acid
• CAS NO: 4279-77-0
• Molecular Formula: C₉H₈O₃S
• Molecular Weight: 196.22
• Mol File: 4279-77-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Solubility: Acetone; Chloroform; Methanol
• CAS DataBase Reference: MONOTHIOLPHENYL MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: MONOTHIOLPHENYL MALONATE(4279-77-0)
• EPA Substance Registry System: MONOTHIOLPHENYL MALONATE(4279-77-0)

Safety Data

• Hazardous Substances Data: 4279-77-0(Hazardous Substances Data)

Usage

Uses

3-Oxo-3-(phenylthio)propanoic Acid is an intermediate in synthesizing Difethialone (D445450), is an anticoagulant rodenticide widely used to control rodent infestations.

Upstream product

• 141-82-2 malonic acid 
• 108-98-5 thiophenol 
• 51932-41-3 malonic acid monochloride 
• 1663-67-8 malonoyl dichloride 
• 80282-54-8 tert-butyl 3-oxo-3-(phenylthio)propanoate 

Downstream Products

• 934-87-2 S-phenyl thioacetate 
• 40053-29-0 S-phenyl 3-oxobutanethioate 
• 1323421-18-6 C₂₂H₂₀ClNO₃S₂ 
• 121788-80-5 (R)-3-Hydroxy-3-phenyl-thiopropionic acid S-phenyl ester 

Relevant articles and documents

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Organocatalytic enantioselective decarboxylative aldol reaction of malonic acid half thioesters with aldehydes

Copycat: A highly enantioselective biomimetic aldol reaction of malonic acid half thioesters with a variety of aldehydes affords optically active β-hydroxy thioesters by employing the cinchona-derived sulfonamide organocatalyst 1. The synthetic utility of this protocol was demonstrated by performing formal syntheses of the antidepressants (R)-fluoxetine, (R)-tomoxetine, (-)-paroxetine, and (R)-duloxetine. Copyright

Expanding the utility of Bronsted base catalysis: Biomimetic enantioselective decarboxylative reactions

As a result of the low reactivity of simple esters, the use of them as nucleophiles in direct asymmetric transformations is a long-standing challenge in synthetic organic chemistry. Nature approaches this difficulty through a decarboxylative mechanism, which is used for polyketide synthesis. Inspired by nature, we report guanidine-catalyzed biomimetic decarboxylative C-C and C-N bond-formation reactions. These highly enantioselective decarboxylative Mannich and amination reactions utilized malonic acid half thioesters as simple ester surrogates. It is proposed that nucleophilic addition precedes decarboxylation in the mechanism, which has been investigated in detail through the identification of intermediates by using electrospray ionization (ESI) mass-spectrometric analysis and DFT calculations. Copyright