1517-82-4

Basic information

• Product Name: (1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE
• Synonyms: (S)-(-)-Menthyl p-toluenesulfinate, (-)-(1R)-Menthyl (S)-p-toluenesulfinate;4-Methylbenzenesulfinic acid (1R)-2α-isopropyl-5β-methylcyclohexane-1β-yl ester;4-Methylbenzenesulfinic acid (1R,3R,4S)-p-menthane-3-yl ester;p-Toluenesulfinic acid (1R,1β)-2α-isopropyl-5β-methylcyclohexyl ester;p-Toluenesulfinic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester;p-Toluenesulfinic acid (1R,3R,4S)-menthyl ester;p-Toluenesulfinic acid (1R,3R,4S)-p-menthane-3-yl ester;(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate,98%
• CAS NO: 1517-82-4
• Molecular Formula: C₁₇H₂₆O₂S
• Molecular Weight: 294.45
• Product Categories: Chiral Building Blocks;Organic Building Blocks;Sulfonates/Sulfinates;chiral;Asymmetric Synthesis;Biochemistry;Monocyclic Monoterpenes;Synthetic Organic Chemistry;Terpenes
• Mol File: 1517-82-4.mol
• Article Data: 41

Chemical Properties

• Melting Point: 99-104 °C
• Boiling Point: 402.342 °C at 760 mmHg
• Flash Point: 197.13 °C
• Appearance: Yellow to brown or gray/Solution
• Density: 1.08
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -199 ° (C=1.5, Acetone)
• Storage Temp.: −20°C
• Solubility: Acetone (Slightly), Chloroform (Slightly)
• BRN: 3207468
• CAS DataBase Reference: (1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE(1517-82-4)
• EPA Substance Registry System: (1R,2S,5R)-(-)-MENTHYL (S)-P-TOLUENESULFINATE(1517-82-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1517-82-4(Hazardous Substances Data)

Usage

Description

(1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate is a white crystalline powder that is primarily utilized for the introduction of the p-toluenesulfinyl group in asymmetric synthesis. (1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate plays a crucial role in the formation of various complex molecules, particularly in the field of organic chemistry.

Uses

1. Chemical Synthesis:
(1R,2S,5R)-(-)-Menthyl (S)-p-Toluenesulfinate is used as a reactant in the synthesis of sulfoxide pincer complexes of Mg, Rh, and Ir. These complexes are essential in various chemical reactions and applications, contributing to the development of new materials and compounds.
2. Enantiopure Synthesis:
It is also used as a reactant to react with metal ketimines, leading to the formation of enantiopure sulfinimines. Enantiopure compounds are crucial in the pharmaceutical industry, as they can have different biological activities and are often required for the development of new drugs.
3. Chiral Auxiliary:
(1R,2S,5R)-(-)-Menthyl (S)-p-toluenesulfinate can react with p-(methylthio)benzaldehyde to form (S)-(-)-N-(4-methylthiobenzylidene)-p-toluenesulfinimine, which is a chiral auxiliary. Chiral auxiliaries are essential in asymmetric synthesis, as they help to control the stereochemistry of the resulting products, leading to the formation of specific enantiomers with desired properties.

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?/m1/s1

Upstream product

• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 2216-51-5 (-)-menthol 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 103-19-5 di(p-tolyl) disulfide 
• 788-86-3 p-tolylsulfinyl p-tolyl sulfone 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 158009-86-0 (S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate 
• 216855-44-6 (R)-2-Benzyl-3,3,3-trifluoro-2-((S)-toluene-4-sulfinylamino)-propionic acid methyl ester 
• 188447-91-8 (S)-p-toluenesulfinimide 
• 216855-39-9 (S)-N-(p-tolylsulfinylimino)triphenylphosphorane 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 

Downstream Products

• 30506-35-5 (R)-1-(butylsulfinyl)-4-methylbenzene 
• 50299-85-9 (R_s)-(+)-p-toluenesulfinylcyclopropane 
• 10381-68-7 (S)-2-methyl-1-(p-tolylsulfinyl)benzene 
• 20268-15-9 (-)-(S)-mesityl p-tolyl sulphoxide 
• 33418-16-5 (-)-(R,Z)-1-(p-methylphenylsulfinyl)prop-1-ene 
• 21179-27-1 (S)-(+)-N,N,4-trimethylbenzenesulfinamide 
• 66967-38-2 (+)-(R)_S-(E)-1-(p-tolylsulfinyl)oct-1-ene 
• 61783-64-0 (+)-(S)-1-hexynyl p-tolyl sulfoxide 
• 59336-69-5 (R)-α-Methylvinyl-tolyl-sulfoxid 
• 123642-79-5 (+)-(R)-4,5-dihydro-2-<<(4-methylphenyl)sulfinyl>methyl>-3H-pyrrole 
• 128949-52-0 (R)-(+)-2-<(4-methylphenyl)sulfinylmethyl>pyridine 
• 143810-74-6 (Ss)-2-(p-tolylsulfinyl)-furane 
• 143810-77-9 (S_S)-2-(p-tolylsulfinyl)thiophene 

Relevant articles and documents

Stereochemistry of organic sulfur compounds: More than 100?years of history, current state and further challenges

In the paper presented are the author's subjective views on the most important achievements in the stereochemistry of organic sulfur compounds, which, as an object of research, has more than 100-year history. Prospects for further development are also men

Efficient Synthesis of Sulfinate Esters and Sulfinamides via Activated Esters of p -Toluenesulfinic Acid

Sulfinate esters were prepared by the process of activating p -toluenesulfinic acid with either cyanuric chloride, methanesulfonyl chloride, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl). Activation of p -toluenesulfinic acid with cyanuric chloride led to the formation of sulfinate esters that were accompanied by the formation of the corresponding sulfones. The use of methanesulfonyl chloride for activation via methanesulfonic p -toluenesulfinic anhydride afforded mixtures of sulfinate esters and methanesulfonates. The use of the carbodiimide EDC proved to yield the best results with the highly selective formation of the target sulfinate esters. The use of trimethylacetic p -toluenesulfinic anhydride or cyanuric chloride to achieve the synthesis of sulfinamides proved to be ineffective due to poor chemoselectivity of the nucleophilic attack on the activated p -toluenesulfinic acid anhydride. Ultimately, the use of EDC-HCl to form the sulfinamides proved to be the best pathway for synthesis.

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.

Palladium-Catalyzed Enantioselective C?H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization

The first example of PdII-catalyzed enantioselective C?H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) throu