50444-99-0

Basic information

• Product Name: (1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENE-
• Synonyms: (1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENE-
• CAS NO: 50444-99-0
• Molecular Formula: C₁₇H₂₆O₂S
• Molecular Weight: 230.38834
• Mol File: 50444-99-0.mol

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Boiling Point: 402.3°C at 760 mmHg
• Flash Point: 197.1°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 2.57E-06mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: (1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENE-(CAS DataBase Reference)
• NIST Chemistry Reference: (1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENE-(50444-99-0)
• EPA Substance Registry System: (1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENE-(50444-99-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 50444-99-0(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
(1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENEis used as a chiral auxiliary in asymmetric synthesis for its ability to induce selectivity in chemical reactions, leading to the formation of enantiomerically pure products.
Used in Organic Chemistry Reactions:
(1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENEis utilized as a chiral auxiliary in various organic chemistry reactions to enhance the stereoselectivity and yield of desired enantiomers, which is crucial for the development of pharmaceuticals and other chiral compounds.
Used in Chemical Synthesis and Drug Discovery Research:
(1S 2R 5S)-(+)-MENTHYL (R)-P-TOLUENEserves as a valuable tool in research and development for its potential applications in the synthesis of complex molecules and the discovery of new drugs, thanks to its intricate structure and chiral nature.

InChI:InChI=1/C17H26O2S/c1-12(2)16-10-7-14(4)11-17(16)19-20(18)15-8-5-13(3)6-9-15/h5-6,8-9,12,14,16-17H,7,10-11H2,1-4H3/t14-,16+,17-,20+/m0/s1

Upstream product

• 2216-51-5 (-)-menthol 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 103-19-5 di(p-tolyl) disulfide 
• 15356-70-4 menthol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 100-51-6 benzyl alcohol 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 89-78-1 menthol 

Downstream Products

• 219922-11-9 N-<(R)-phenyl-(2-(1-piperidinyl)phenyl)-methyl>-N-<(S')-p-toluene-sulfinyl>-amine 
• 219922-12-0 N-<(S)-phenyl-(2-(1-piperidinyl)phenyl)-methyl>-N-<(S')-p-toluene-sulfinyl>-amine 
• 229179-87-7 (R)-3-(p-tolylsulfinyl)pyridine 
• 229179-84-4 (R)-3,6-dimethoxy-4-(p-tolylsulfinyl)pyridazine 
• 232932-73-9 3-Isopropyl-4-methyl-1-((S)-toluene-4-sulfinyl)-pent-1-yn-3-ol 
• 274676-98-1 (+)-(Ss,2R,3S)-2-diphenylphosphoryl-3-methyl-N-p-toluenesulfinylaziridine 
• 274676-97-0 (+)-(Ss,2S,3R)-2-diphenylphosphoryl-3-methyl-N-p-toluenesulfinylaziridine 
• 274677-07-5 (-)-(Ss,2R,3S)-2-diphenylphosphoryl-3-ethyl-N-p-toluenesulfinylaziridine 
• 274677-06-4 (-)-(Ss,2S,3R)-2-diphenylphosphoryl-3-ethyl-N-p-toluenesulfinylaziridine 
• 288159-10-4 (R)-N-p-tolylsulfinyl tryptamine 
• 267899-26-3 8,8-Dimethyl-6-((S)-toluene-4-sulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene 
• 234436-57-8 (S_S)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol 
• 2509221-06-9 (S)-4-phenyl-2-(2-((R)-p-tolylsulfinyl)phenyl)-4,5-dihydrooxazole 
• 392662-71-4 (R)-N-p-tolylsulfinyl 2-(3,4-dimethoxy)phenylethylamine 

Relevant articles and documents

Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism

Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.

Synthesis of enantiopure sulfonimidamides and elucidation of their absolute configuration by comparison of measured and calculated CD spectra and X-ray crystal structure determination

Straightforward syntheses of enantiopure N-benzoyl- and N-tert-butyloxycarbonyl-protected sulfonimidamides, which can be used as building blocks in newly designed catalysts, are presented. Key synthetic step is a dynamic resolution of a racemic sulfinic acid sodium salt. All subsequent transformations proceed stereospecifically. The absolute configurations at the sulfur atoms of both sulfonimidamides were determined by comparison of measured and calculated CD spectra. An X-ray crystal structure determination of a sulfonimidoylguanidine derivative confirmed this result.

An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions

The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.

p-Tolylsulfinyl Amides: Reagents for Facile Electrophilic Functionalization of Olefins

A variety of olefins were found to react with sulfinyl amides in the presence of POCl3 to give β-chlorosulfides and β-hydroxysulfides in good yields. In the absence of nucleophiles, p-tolylsulfinyl amides were found to react with olefins with the formation of allylsulfoxides.

Highly diastereoselective synthesis and easy method for synthesis of optically active sulfinate esters from aromatic disulfides

One-step synthesis of chiral aromatic sulfinate esters 2 from aromatic disulfides 1 using lead tetraacetate is reported. The yields are good to excellent and diastereoselectivity is high.

An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine

An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphos

A convenient and highly diastereoselective synthesis of optically active sulfinate esters from sulfonyl chlorides under solid state conditions

A manipulatively simple and rapid method for synthesis of chiral sulfinate esters 1 and 2 from sulfonyl chloride and trimethyl phosphite in solid phase conditions supported on silica gel is described. The chemical yields are good to excellent and diastereoselectivity is high.

O-sulfinylation with methanesulfonyl cyanide or p-toluenesulfonyl cyanide and DBU

Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates is suggested.

SYNTHESES ASYMETRIQUES DE β-HYDROXYACIDES PAR CONDENSATION D'ANIONS ENOLATES D'ESTERS α-SULFINYLE CHIRAUX SUR DES COMPOSES CARBONYLES

A stereospecific synthesis of (R)-(+)-t-butyl p-tolylsulfinyl acetate 2 is described.The aldol-type condensation of this reagent leads to β-hydroxyacids in good chemical and optical yields.The determination of the absolute configuration of the condensatio