57651-34-0

Basic information

• Product Name: (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE)
• Synonyms: (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE)
• CAS NO: 57651-34-0
• Molecular Formula: C₁₀H₁₃ClNOPS
• Molecular Weight: 261.708081
• Mol File: 57651-34-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE)(57651-34-0)
• EPA Substance Registry System: (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE)(57651-34-0)

Safety Data

• Hazardous Substances Data: 57651-34-0(Hazardous Substances Data)

Usage

Description

(2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE, also known as N-sulfinyl-2-(2-chloro-5-methylphenyl)-1,3,2-oxazaphospholidine, is a chiral oxazaphospholidine with a sulfinyl group. It has the molecular formula C8H9ClNOPS and is known for its strong odor and potential toxic effects. This chemical compound is utilized in various applications, particularly in the field of asymmetric catalysis and organic synthesis.

Uses

Used in Asymmetric Catalysis:
(2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE is used as a reagent in asymmetric catalysis for the asymmetric addition of alkyl zinc reagents to aldehydes and enones. Its chiral structure allows for the selective formation of specific enantiomers, which is crucial in the synthesis of biologically active compounds and pharmaceuticals.
Used in Organic Synthesis:
In the field of organic synthesis, (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE is employed as a reagent for various asymmetric transformations. Its unique properties enable the synthesis of complex organic molecules with high enantioselectivity and efficiency.
Used in Pharmaceutical Industry:
(2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its ability to facilitate asymmetric reactions contributes to the production of enantiomerically pure drugs, which is essential for ensuring the desired therapeutic effects and minimizing side effects.
Safety Precautions:
Due to its strong odor and potential toxic effects, (2S,4S,5R)-(-)-2-CHLORO-3,4-DI-ME-5-PH-1,3,2-OXAZAPHOSPHOLIDINE 2-SULFIDE requires proper handling and storage. It is essential to follow safety guidelines and use appropriate personal protective equipment when working with this compound to minimize health risks and environmental contamination.

Upstream product

• 50-98-6 ephedrine hydrochloride 
• 299-42-3 ephedrine 
• 3982-91-0 trichlorothiophosphine 
• 90-82-4 pseudoephedrine 
• 57573-32-7 (2R,4S,5R)-(-)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine-2-thione 

Downstream Products

• 71877-71-9 4-((2R)-3,4c-dimethyl-5c-phenyl-2-thioxo-2λ⁵-[1,3,2]oxazaphospholidin-2r-yl)-morpholine 
• 1089310-25-7 (2S,4S,5R)-2-ethoxy-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine-2-thione 
• 66193-90-6 (4S)-3,4r-dimethyl-2-(4-nitro-phenoxy)-5c-phenyl-[1,3,2]oxazaphospholidine 2t-sulfide 
• 91279-88-8 (2S,4S,5R)-3,4-Dimethyl-2-((S)-1-methyl-heptyloxy)-5-phenyl-[1,3,2]oxazaphospholidine 2-sulfide 
• 91228-11-4 (2S,4S,5R)-2-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-3,4-dimethyl-5-phenyl-[1,3,2]oxazaphospholidine 2-sulfide 
• 66007-24-7 ((2R,4S,5R)-3,4-Dimethyl-5-phenyl-2-thioxo-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-((S)-1-phenyl-ethyl)-amine 
• 57573-33-8 (2R,4S,5R)-2-methoxy-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide 
• 68027-91-8 (2S,4S,5R)-2-methylthio-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine-2-one 
• 79236-66-1 (S)-Thiophosphoric acid O-ethyl ester S-methyl ester O'-((1R,2S)-2-methylamino-1-phenyl-propyl) ester; hydrochloride 
• 66193-93-9 (S)-Thiophosphoric acid O-ethyl ester O'-methyl ester O''-((1R,2S)-2-methylamino-1-phenyl-propyl) ester 
• 66193-93-9 (R)-Thiophosphoric acid O-ethyl ester O'-methyl ester O''-((1R,2S)-2-methylamino-1-phenyl-propyl) ester 
• 66193-94-0 (S)-Thiophosphoric acid O-isopropyl ester O'-methyl ester O''-((1R,2S)-2-methylamino-1-phenyl-propyl) ester 
• 66193-94-0 (R)-Thiophosphoric acid O-isopropyl ester O'-methyl ester O''-((1R,2S)-2-methylamino-1-phenyl-propyl) ester 

Relevant articles and documents

Novel methods for ester detoxication

This invention relates to a method for detoxication of inorganic or organic esters including OP nerve agents, cocaine, and respective analogs. More specifically, this invention pertains to the treatment of potentially neurotoxic esters or other ester grou

Intermolecular effects on the radiogenic formation of electron-capture phosphorus-centered radicals. A single-crystal ESR study of diastereoisomeric precursors

ESR experiments on X-irradiated single crystals of the 2R,4S,5R and 2S,4S,5R diastereoisomers of 2-chloro3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide reveal that the yield of radiogenic electron-capture reactions in the solid state strongly depends on intermolecular interactions in the crystal. In the present case a high yield of P-Cl three-electron-bond phosphoranyl radical anions is found in crystals of the 2R,4S,5R isomer, whereas no radical formation can be detected for the 2S,4S,5R isomer. An analysis of nonbonded interactions with neighboring molecules reveals that the geometry relaxation necessary for the radical stabilization is easily accommodated in crystals of the 2R,4S,5R isomer but not in the 2S,4S,5R isomer, explaining the observed difference in electron-capture efficiency. Experiments on radical formation in a MeTHF host matrix give further insight into the importance of the environment on radiogenic radical formation. The possible concurrent effect of the matrix on the electronic configuration and spin density distribution of the resulting phosphoranyl radical is discussed.