119461-40-4

Basic information

• Product Name: (S)-1-Tosyl-2-methylaziridine
• Synonyms: (S)-1-Tosyl-2-methylaziridine;(S)-2-Methyl-1-[(4-methylphenyl)sulfonyl]aziridine
• CAS NO: 119461-40-4
• Molecular Formula: C₁₀H₁₃NO₂S
• Molecular Weight: 211.28
• Product Categories: Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 119461-40-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 56-58 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 326.2°C at 760 mmHg
• Flash Point: 151.1°C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 0.00022mmHg at 25°C
• Refractive Index: 1.58
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: -6.39±0.40(Predicted)
• CAS DataBase Reference: (S)-1-Tosyl-2-methylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Tosyl-2-methylaziridine(119461-40-4)
• EPA Substance Registry System: (S)-1-Tosyl-2-methylaziridine(119461-40-4)

Safety Data

• Hazardous Substances Data: 119461-40-4(Hazardous Substances Data)

Usage

Description

(S)-1-Tosyl-2-methylaziridine, with the chemical name (2S)-8-methyl-8-tosyl-1-azabicyclo[3.2.0]heptane, is a chiral compound characterized by its unique aziridine ring structure. It is a brown solid with a specific stereochemistry, which is crucial for its applications in organic synthesis. (S)-1-Tosyl-2-methylaziridine is identified by its CAS number 119461-40-4.

Uses

Used in Organic Synthesis:
(S)-1-Tosyl-2-methylaziridine is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure and reactivity make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. (S)-1-Tosyl-2-methylaziridine's chirality and stability contribute to its utility in creating enantioselective products, which are essential in many biologically active molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-1-Tosyl-2-methylaziridine is used as a key intermediate in the synthesis of chiral drugs. Its specific stereochemistry allows for the development of enantiomerically pure compounds, which is critical for ensuring the desired biological activity and minimizing potential side effects. (S)-1-Tosyl-2-methylaziridine's role in drug synthesis can lead to the creation of new medications with improved efficacy and safety profiles.
Used in Research and Development:
(S)-1-Tosyl-2-methylaziridine is also utilized in academic and industrial research settings for the exploration of new synthetic methods and the development of innovative chemical processes. Its unique properties make it an interesting subject for studying reaction mechanisms, catalysts, and other aspects of organic chemistry. Additionally, it can be used to test and validate new synthetic strategies and techniques in the field of asymmetric synthesis.

InChI:InChI=1/C10H13NO2S/c1-8-3-5-10(6-4-8)14(12,13)11-7-9(11)2/h3-6,9H,7H2,1-2H3/t9-,11?/m0/s1

Upstream product

• 88129-44-6 (S)-N-(p-toluenesulfonyl)-2-amino-1-propyl p-toluenesulfonate 
• 2749-11-3 (S)-Alaninol 
• 98-59-9 p-toluenesulfonyl chloride 
• 100132-60-3 (S)-2-(toluene-4-sulfonamido)propan-1-ol 
• 56-41-7 L-alanin 
• 4816-81-3 p-tosyl-L-alanine 
• 59724-69-5 (S)-N-tosylalanine methyl ester 

Downstream Products

• 119461-41-5 (S)-N-(p-toluenesulfonyl)-4-amino-1-(trimethylsilyl)-1-pentyne 
• 196520-91-9 N(CH₂CH(Me)NH(4-CH₃(C₆H₄)SO₂))3 
• 362495-77-0 [2S,4S,1'S,2'S]-(+)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide 
• 406937-95-9 N-[(1S)-2-(1-benzothien-3-yl)-1-methylethyl]-4-methylbenzenesulfonamide 
• 34542-12-6 4-methyl-N-[(1S)-1-methyl-2-phenylethyl]benzenesulfonamide 
• 406937-96-0 4-methyl-N-[(1S)-1-methyl-2-(1-naphthyl)ethyl]benzenesulfonamide 
• 1027839-81-1 C₂₃H₃₆N₄O₄S₂ 
• 460743-46-8 N-[(1S)-2-(benzylamino)-1-methylethyl]-4-methylbenzenesulfonamide 
• 460743-51-5 N-{(1S)-2-[benzyl((2S)-{[(4-methylphenyl)sulfonyl]amino}propyl)amino]-1-methylethyl}-4-methylbenzenesulfonamide 
• 462119-78-4 4-methyl-N-{(1S)-1-methyl-2-[((2S)-2-{[(4-methylphenyl)sulfonyl]amino}propyl)amino]ethyl}benzenesulfonamide 
• 670069-56-4 [(1S)-2-amino-1-methylethyl]-4-methylbenzenesulfonamide 

Relevant articles and documents

A general method for the preparation of chiral TREN derivatives

A general procedure for the preparation of C3-symmetric TREN derivatives with backbone chirality has been developed. Stereo- and regioselective ring opening by ammonia of (S)-N-tosyl-2-isopropylaziridine, obtained starting from either the corre

Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids

We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In pa

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.