2658-24-4

Basic information

• Product Name: 2,2-dimethylaziridine
• Synonyms: 2,2-Dimethylethyleneimine;AI3-50669;Aziridine, 2,2-diMethyl-
• CAS NO: 2658-24-4
• Molecular Formula: C₄H₉N
• Molecular Weight: 71.12096
• EINECS: 220-191-6
• Mol File: 2658-24-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 49°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.78g/cm³
• Vapor Pressure: 295mmHg at 25°C
• Refractive Index: 1.413
• PKA: 8.28±0.40(Predicted)
• CAS DataBase Reference: 2,2-dimethylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethylaziridine(2658-24-4)
• EPA Substance Registry System: 2,2-dimethylaziridine(2658-24-4)

Safety Data

• Hazardous Substances Data: 2658-24-4(Hazardous Substances Data)

Usage

Purification Methods

Dry the 2,2-dimethylaziridine over solid KOH, filter and freshly distil from sodium before use, and store it under dry nitrogen. The N-phenylthiocarbamoyl derivative crystallises from pet ether containing a trace of Me2CO with m 92.5-93.5o. [Hassner et al. J Am Chem Soc 91 5046 1969, Cairns J Am Chem Soc 63 871 1941, Lamaty et al. Justus Liebigs Ann Chem 726 77 1969, Beilstein 20 III/IV 280.]

InChI:InChI=1/C4H9N/c1-4(2)3-5-4/h5H,3H2,1-2H3

Upstream product

• 124-68-5 2-Amino-2-methyl-1-propanol 
• 4879-95-2 4,4-dimethyl-azetidin-2-one 
• 7732-18-5 water 
• 108343-17-5 2,2-Dimethyl-aziridine-1-carboxylic acid (4-chloro-phenyl)-amide 
• 105-53-3 diethyl malonate 
• 927-82-2 2-amino-2-methylpropyl hydrogensulfate 

Downstream Products

• 77376-91-1 cis-β-(2,2-dimethylethyleneimino)acrylonitrile 
• 95081-57-5 (2,2-Dimethyl-aziridin-1-yl)-propynoic acid methyl ester 
• 73882-21-0 2-Chloroacetamido-3-(2',2'-dimethylaziridino)-1,4-naphthoquinone 
• 129835-31-0 3',5'-diacetyl-N⁴--2'-deoxycytidine 
• 129835-23-0 5'-O-acetyl-3'-O-<carbamoyl>thymidine 
• 129835-20-7 3'-O-(tert-butyldimethylsilyl)-5'-O-<carbamoyl>thymidine 
• 129835-21-8 5'-O-(tert-butyldimethylsilyl)-3'-O-<carbamoyl>thymidine 
• 129835-24-1 3'-O-acetyl-5'-O-<carbamoyl>thymidine 
• 129835-28-5 N⁴--2',3',5'-triacetylcytidine 
• 129835-33-2 N⁴--1-(2',3',5'-triacetyl-β-D-arabinosyl)cytosine 
• 105798-97-8 4-nitrobenzyl carbamate 
• 105799-00-6 2-nitrobenzyl carbamate 
• 98943-68-1 2,2-dimethyl-1-(4-phenylbenzoyl)aziridine 
• 2191-60-8 1,1-dimethyl-2-(phenylthio)ethylamine 

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.

A new route towards N-(α-methoxybenzyl)aziridines

A new synthesis of N-(α-methoxyarylmethyl)-2,2-dimethylaziridines is presented. Different benzaldehydes were converted into the corresponding imines upon reaction with 2-bromo-2-methylpropylamine. Treatment of the latter imines with sodium methoxide affor

Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors

Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C-C bond formation remains challenging. Herein, we describe the development of a TiIII-catalyzed radical addition of 2° and 3° alkyl chlorides to electron-deficient alkenes. Mechanistic data are consistent with inner-sphere activation of the C-Cl bond featuring TiIII-mediated Cl atom abstraction. Evidence suggests that the active TiIII catalyst is generated from the TiIV precursor in a Lewis-acid-assisted electron transfer process.