83647-99-8

Basic information

• Product Name: (R)-2-Methylaziridine
• Synonyms: R-2-Methylaziridine
• CAS NO: 83647-99-8
• Molecular Formula: C₃H₇N
• Molecular Weight: 57.09
• Mol File: 83647-99-8.mol

Chemical Properties

• Boiling Point: 66.5 °C at 760 mmHg
• Appearance: /
• Density: 0.824 g/cm³
• CAS DataBase Reference: (R)-2-Methylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Methylaziridine(83647-99-8)
• EPA Substance Registry System: (R)-2-Methylaziridine(83647-99-8)

Safety Data

• Hazardous Substances Data: 83647-99-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-Methylaziridine is used as a building block in organic synthesis for the development of pharmaceutical drugs. Its reactive nature allows for the creation of various drug molecules, contributing to the advancement of medicinal chemistry.
Used in Organic Synthesis:
(R)-2-Methylaziridine is used as a key intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new chemical entities and the modification of existing ones.

Upstream product

• 42163-48-4 (R)-2-aminopropyl hydrogen sulfate 
• 2799-17-9 (S)-1-amino-2-propanol 
• 126301-26-6 (R)-2-aminopropanol methanesulfonate hydrochloride 
• 75-55-8 2-Methylaziridine 

Relevant articles and documents

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.