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Usage

Uses

Used in Organic Synthesis:
(-)-Benzotetramisole is used as a chiral auxiliary for enhancing the selectivity and yield in the asymmetric synthesis of various biologically active compounds and pharmaceuticals. Its presence helps in achieving the desired enantioselectivity, which is crucial for the production of enantiomerically pure compounds.
Used in Pharmaceutical Industry:
(-)-Benzotetramisole is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with improved efficacy and selectivity. Its role in the production of optically pure amino alcohols and heterocycles is particularly noteworthy, as these are vital building blocks in medicinal chemistry.
Used in Chemical Research:
(-)-Benzotetramisole is utilized as a research tool in the study of asymmetric synthesis and the development of novel synthetic methodologies. Its unique properties allow chemists to explore new reaction pathways and improve existing synthetic processes.
Used in Medicinal Chemistry:
(-)-Benzotetramisole is used as a starting material or intermediate in the preparation of compounds with potential antiparasitic, antiviral, and immunomodulatory properties. Its versatility in organic synthesis makes it a valuable asset in the discovery and development of new therapeutic agents.
Overall, (-)-Benzotetramisole is a multifaceted chemical compound with a wide range of applications in the fields of organic synthesis, pharmaceuticals, chemical research, and medicinal chemistry. Its ability to improve the synthesis of biologically active compounds and its potential pharmacological activities make it an indispensable tool in the advancement of modern chemistry and drug development.

InChI:InChI=1/C15H12N2S/c1-2-6-11(7-3-1)12-10-17-13-8-4-5-9-14(13)18-15(17)16-12/h1-9,12H,10H2/t12-/m1/s1

Upstream product

• 1141-88-4 2-Aminophenyl disulfide 
• 1235891-51-6 (S)-N-(2-benzothiazolyl)-2-hydroxy-1-phenylethylamine 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 20989-17-7 (2S)-2-phenylglycinol 

Relevant academic research and scientific papers

In Situ Activation of Disulfides for Multicomponent Reactions with Isocyanides and a Broad Range of Nucleophiles

Activation of disulfides with N-halogen succinimide in the presence of TEMPO allows insertion reaction by an isocyanide, the product of which can further accept a wide range of nucleophiles for the generation of isothioureas and related molecular moieties. This new procedure overcomes previous methods that accept essentially only aryl amines as the third nucleophilic component. The diverse nucleophiles usable in our new protocol make this approach a general method for de novo synthesis of many S-containing heterocycles.

A scalable, chromatography-free synthesis of benzotetramisole

The scalable, chromatography-free synthesis of the chiral isothiourea benzotetramisole (BTM) in two steps from commercially available materials is presented. A detailed procedure for the synthesis of both enantiomers and the racemate on ca. 10 gram scale

A scalable, chromatography-free synthesis of benzotetramisole

The scalable, chromatography-free synthesis of the chiral isothiourea benzotetramisole (BTM) in two steps from commercially available materials is presented. A detailed procedure for the synthesis of both enantiomers and the racemate on ca. 10 gram scale

In situ evaluation of kinetic resolution catalysts for nitroaldol by rationally designed fluorescence probe

Development of effective chemical catalysts is a key concern in organic chemistry. Therefore, convenient screening systems for chemical catalysts are required, and although some fluorescence-based HTS systems have been developed, little attempt has been made to apply them to asymmetric catalysts. Therefore, we tried to develop a chiral fluorescence probe which can evaluate the reactivity and enantioselectivity of asymmetric catalysts. We focused on kinetic resolution catalysts as a target of our novel fluorescence probe, employing β-elimination following acylation of nitroaldol. Once the hydroxyl group of nitroaldol is acylated, β-elimination occurs immediately, affording nitro olefin. Therefore, we designed and synthesized a fluorescence probe with an asymmetric nitroaldol moiety. Its fluorescence intensity decreases dramatically upon β-elimination, so the fluorescence decrease is an indicator of the reaction yield. Thus, the enantioselectivity of kinetic resolution catalysts can be assessed simply by measuring the fluorescence intensities of the reaction mixtures of the two enantiomers; it is not necessary to purify the product. This fluorescence probe revealed that benzotetramisole is a superior catalyst for kinetic resolution of nitroaldol. Furthermore, we established an HTS system for asymmetric catalysts, using a fluorescence probe and benzotetramisole. To our knowledge, this is the first fluorescence-based HTS system for asymmetric catalysts.