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
• Article Data: 3

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

General Description

"(R)-2-Methylaziridine, also known as (R)-2-Methylaziridine and (R) -.alpha.-Methylaziridine, is a chemical compound classified as an isomer. The compound falls under aziridines' family which are monocyclic, saturated compounds with three carbon atoms in the ring. Due to its reactive nature, it is often used as a building block in organic synthesis, particularly in pharmaceutical drug manufacturing. However, it's important to note that (R)-2-Methylaziridine is quite unstable and can be potentially toxic and hazardous, making careful handling a must when dealing with this chemical. Its precise physical and chemical properties may vary, often depending on its purity and specific preparation techniques.

Upstream product

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

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.

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.