52340-20-2

Basic information

• Product Name: (S)-2-Methylaziridine
• Synonyms: (S)-2-METHYL AZIRIDINE;Aziridine, 2-methyl-, (2S)-
• CAS NO: 52340-20-2
• Molecular Formula: C₃H₇N
• Molecular Weight: 57.09
• Mol File: 52340-20-2.mol

Chemical Properties

• Boiling Point: 66.5 °C at 760 mmHg
• Appearance: /
• Density: 0.824g/cm³
• Refractive Index: 1.413
• PKA: 8.21±0.40(Predicted)
• CAS DataBase Reference: (S)-2-Methylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Methylaziridine(52340-20-2)
• EPA Substance Registry System: (S)-2-Methylaziridine(52340-20-2)

Safety Data

• Hazard Codes: T
• Statements: 11-34-41-37/38-25
• Safety Statements: 16-26-36-45-39
• RIDADR: 2733
• Hazardous Substances Data: 52340-20-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Methylaziridine is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the creation of chiral amines and heterocyclic compounds, which are crucial in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-2-Methylaziridine serves as a key intermediate, facilitating the production of compounds that are integral to the development of pesticides and other agricultural chemicals.
Used in Specialty Chemicals Industry:
(S)-2-Methylaziridine is utilized as a versatile building block in the synthesis of specialty chemicals, where its unique properties allow for the creation of complex and specific chemical structures.
Used in Asymmetric Synthesis:
(S)-2-Methylaziridine is employed as a reagent in asymmetric synthesis, a technique that is vital for producing enantiomerically pure compounds, which are often necessary for biological activity and pharmaceutical applications.
Used in Natural Product Modification:
(S)-2-Methylaziridine has been studied for its potential use in the modification of natural products, where it can be employed to alter the properties or functions of naturally occurring substances, enhancing their utility in various applications.

InChI:InChI=1/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3/t3-/m1/s1

Upstream product

• 75-55-8 2-Methylaziridine 
• 946088-68-2 benzyl 2-methylaziridine-1-carboxylate 
• 119461-40-4 S-(+)-2-methyl-N-p-tosylaziridine 
• 126301-21-1 (S)-2-aminopropanol methanesulfonate hydrochloride 
• 2799-16-8 (2R)-hydroxypropylamine 
• 2749-11-3 (S)-Alaninol 
• 114080-83-0 2-ammoniopropyl sulfate 

Downstream Products

• 110481-01-1 (2S,9S)-4,7-diphenyl-4,7-diphosphodecane-2,9-diamine 
• 122673-70-5 (S)-1-methyl-2-phenylsylfanylethylamine 
• 1564287-62-2 C₁₃H₂₃NO 
• 4680-24-4 cis-(R)-limonene oxide 
• 1430334-91-0 C₁₂H₁₃NO₃ 
• 1430334-89-6 C₁₈H₁₇NO₃ 
• 1202556-45-3 C₁₉H₂₁NO₃S 
• 946088-68-2 benzyl 2-methylaziridine-1-carboxylate 

Relevant articles and documents

Synthesis and evaluation of biological activities of aziridine derivatives of urea and thiourea

In the present paper, we report the synthesis and evaluation of in vitro antimicrobial activities of aziridine-thiourea derivatives. A series of aziridines in reaction with isocyanates and isothiocyanates to obtain urea and thiourea derivatives were used.

Scalable synthesis of N -acylaziridines from N -tosylaziridines

N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N

Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step

Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β3-amino nitriles into their corresponding N-protected β3-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β3-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β3-amino nitriles. Two simple and efficient procedures to prepare the β3-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.

A new and expeditious asymmetric synthesis of (R)- and (S)-2-aminoalkanesulfonic acids from chiral amino alcohols

The mechanism for the transformation of β-amino alcohol methanesulfonate hydrochlorides into sodium β-amino alkanesulfonates using sodium sulfite was investigated. The results show that sodium sulfite initially neutralizes the β-amino alcohol methanesulfonate hydrochloride to give a free β-amino alcohol methanesulfonate, which then cyclizes to a 2-alkylaziridine. Attack by the previously formed sodium bisulfite at the less hindered carbon atom of the aziridine ring then yields a β-amino alkanesulfate sodium salt. Based on this mechanistic proposal, a new and rapid asymmetric synthesis of (R)- and (S)-2-aminoalkanesulfonic acids from chiral amino alcohols was developed. Chiral amino alcohols were converted to chiral aziridines through the Wenker method or Mitsunobu reaction and the resulting aziridines were reacted with sodium bisulfite to produce chiral β-amino alkanesulfonic acids.

Efficient Optical Resolution of Aziridines with Optically active host compounds

Some aziridines are resolved efficiently by complexation with optically active host compounds which were derived from tartaric acid.

STEREOCHEMISTRY OF THE RING CLOSURE REACTION OF OPTICALLY ACTIVE 1-AMINO-2-PROPANOL

Optically active 2-methylethylenimine has been prepared via ring closure reaction of (R)- or (S)- 1-amino-2-propanol.The reaction is explained by an intramolecular SN mechanism.

Chiroptical properties of 2-alkylaziridines and their N-methyl derivatives

Some optically active 2-alkylaziridines and their N-methyl derivatives have been prepared from the corresponding L-amino acids.Both the ORD and the CD spectra of the aziridines have been determined.From these spectra it is concluded that a cis orientation of the lone pair of the nitrogen, relative to the 2-alkyl substituent, can be correlated with a negative Cotton effect in the 200 nm region.

Asymmetrical nonbridgehead nitrogen-IV. Chiroptical properties of the amines, N-chloroamines and cyanamides

The ORD and CD spectra of 2-methyl-aziridine, azetidine, pyrrolidine, piperidine, their N-Me, N-Hal, N-CN derivatives as well as those of camphidine, N-methyl- and N-cyano-camphidine have been investigated. The possibility of application of the quadrant rule for N-chloroamines is discussed. A similar rule is proposed for the N-CN chromophore.