57057-80-4

Basic information

• Product Name: L-(-)-O-TOSYLLACTIC ACID ETHYL ESTER
• Synonyms: ETHYL L-(-)-O-(P-TOLUENESULFONYL)LACETATE;ETHYL L(-)-O-(P-TOLUENESULFONYL)LACTATE;ETHYL L-(-)-O-TOSYLLACTATE;Tosyllacticacidethylester;(-)-2-O-(p-Tolylsulfonyl)-L-lactic acid ethyl ester;(S)-2-(Tosyloxy)propionic acid ethyl ester;[S,(-)]-2-[(p-Tolylsulfonyl)oxy]propionic acid ethyl ester;Ethyl L-(-)-O-(p-Toluenesulfonyl)lactate L-(-)-O-(p-Toluenesulfonyl)lactic Acid Ethyl Ester L-(-)-O-Tosyllactic Acid Ethyl Ester
• CAS NO: 57057-80-4
• Molecular Formula: C₁₂H₁₆O₅S
• Molecular Weight: 272.32
• Product Categories: Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry
• Mol File: 57057-80-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: 32 °C
• Boiling Point: 384.321 °C at 760 mmHg
• Flash Point: 32 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -36.5 ° (C=5, CHCl3)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: L-(-)-O-TOSYLLACTIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: L-(-)-O-TOSYLLACTIC ACID ETHYL ESTER(57057-80-4)
• EPA Substance Registry System: L-(-)-O-TOSYLLACTIC ACID ETHYL ESTER(57057-80-4)

Safety Data

• Hazardous Substances Data: 57057-80-4(Hazardous Substances Data)

Usage

General Description

L-(-)-O-Tosyllactic Acid Ethyl Ester is a chemical compound that belongs to the class of tosylates, which are esters of tosyl (p-toluenesulfonyl) acid. It is used as a reagent in organic synthesis, particularly in the preparation of various pharmaceutical intermediates and chiral compounds. L-(-)-O-TOSYLLACTIC ACID ETHYL ESTER has a tosyl group attached to the lactic acid ethyl ester, making it a valuable building block for asymmetric synthesis and chiral resolution. L-(-)-O-Tosyllactic Acid Ethyl Ester is known for its high reactivity and selectivity in chemical reactions, and it is widely used in the pharmaceutical and fine chemical industries for various synthetic applications.

InChI:InChI=1/C12H16O5S/c1-4-16-12(13)10(3)17-18(14,15)11-7-5-9(2)6-8-11/h5-8,10H,4H2,1-3H3/t10-/m0/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 687-47-8 (S)-Ethyl lactate 

Downstream Products

• 51063-99-1 (R)-ethyl 2-bromopropanoate 
• 133608-96-5 (S)-2-tert-Butoxycarbonyl-3-methyl-succinic acid 1-tert-butyl ester 4-ethyl ester 
• 100325-83-5 (R)-ethyl 2-(4-phenoxyphenoxy)propionate 
• 188251-66-3 (R)-2-(4-[1,2,3]Triazol-1-ylmethyl-phenoxy)-propionic acid ethyl ester 
• 835-86-9 (R)-1-ethoxy-1-oxopropan-2-yl benzoate 
• 42411-39-2 (R)-ethyl 2-chloropropanoate 
• 30365-54-9 ethyl (S)-2-bromopropionate 
• 31253-08-4 (L)-2-iodo-propionic acid ethyl ester; l(-)-α-iodo-propionic acid ethyl ester 
• 31253-08-4 (D)-2-iodo-propionic acid ethyl ester; d(+)-α-iodo-propionic acid ethyl ester 
• 7699-00-5 (R)-Ethyl lactate 
• 66513-22-2 (R)-2-(4-chloro-2-methylphenoxy)propionic acid ethyl ester 
• 94051-08-8 quizalofop-p 
• 84028-99-9 diethyl (2R,2′S)-2,2′-iminodipropanoate 
• 1374764-31-4 C₁₂H₁₇NO₅S 

Relevant articles and documents

Synthesis and properties of optically active phenoxypropionates having various cores

Optically active phenoxypropionates having a variety of cores were synthesized and the effect of the different core structures on the spontaneous polarization (Ps) values was investigated. The results indicate that the core structure has a great influence on the Ps value and compound 3 in which a chiral group attached to the 5-phenyl side of the 2,5-diphenylpyrimidine core showed the largest Ps of 240 nC/cm2. The ability as a chiral dopant for ferroelectric liquid crystal (FLC) were also evaluated. It was found that compound 3 was the most interesting, because the doping of compound 3 induced large Ps and wide tilt angle and this FLC mixture showed short response time. Moreover, the Sc range of host liquid crystal mixture are slightly extended by doping of compound 3.

Preparation method of quizalofop-P-ethyl

The invention provides a preparation method of quizalofop-P-ethyl. Ethyl S(-)-tosyllactate is prepared from p-toluenesulfonyl chloride and L-ethyl lactate through a reaction, and quizalofop-P-ethyl is prepared from ethyl S(-)-tosyllactate and 6-chloro-2-(4-hydroxyphenoxy) quinoxaline through a reaction. Ethyl S(-)-tosyllactate is prepared from liquid organic tertiary amine as alkali through reaction in a solvent-free and desiccant-free system, and hydrolysis of L-ethyl lactate is avoided, so that the content of impurities in p-toluenesulfonyl chloride is reduced, the content of impurities in quizalofop-P-ethyl is further reduced, and the chemical content of obtained quizalofop-P-ethyl is 98% or higher, the optical purity is high (R/S is larger than 99/1); operating procedures are simplified, and the production cost is reduced.

Synthesis method of chiral fenoxanil

The invention relates to a synthesis method of chiral fenoxanil. The synthesis method of the chiral fenoxanil is characterized in that chiral ethyl lactate is subjected to sulfonylation reaction to obtain sulfonic acid ester; the sulfonic acid ester reacts with 2,4-dichlorophenol to generate 2-(2,4-dichlorophenoxy) ethyl propionate; the 2-(2,4-dichlorophenoxy) ethyl propionate and 2,-amino-2,3-dimethyl nitrile are subjected to ammonia ester exchange reaction to generate corresponding chiral fenoxanil, wherein the molar ratio of the 2-(2,4-dichlorophenoxy) ethyl propionate to the 2,-amino-2,3-dimethyl nitrile is 1:1 and the reaction temperature is 60 to 85 DEG C. The method is simple in synthesis route, hydrolysis and chlorination are not needed, little waste water and waste gas are generated, a high environmentally-friendly benefit is achieved, the production cost is greatly reduced, the condition is mild, the fenoxanil with optical chirality can be synthesized in an oriented mode by selecting different configuration of ethyl lactate, and important significance of further exploring the optical property of the fenoxanil is achieved.