188818-06-6

Basic information

• Product Name: Aziridine, 2-methylene-1-(phenylmethyl)-
• CAS NO: 188818-06-6
• Molecular Formula: C10H11N
• Molecular Weight: 145.204
• Mol File: 188818-06-6.mol

Chemical Properties

• CAS DataBase Reference: Aziridine, 2-methylene-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Aziridine, 2-methylene-1-(phenylmethyl)-(188818-06-6)
• EPA Substance Registry System: Aziridine, 2-methylene-1-(phenylmethyl)-(188818-06-6)

Safety Data

• Hazardous Substances Data: 188818-06-6(Hazardous Substances Data)

Upstream product

• 865-47-4 potassium tert-butylate 
• 25662-24-2 N-benzyl-2-(bromomethyl)aziridine 
• 100-46-9 benzylamine 
• 72551-10-1 N-(2-bromoallyl)benzylamine 
• 188818-01-1 N-benzylidene-2,3-dibromopropylamine 
• 68003-55-4 benzylidene allylamine 
• 41233-93-6 potassium 2-methylbutan-2-olate 

Downstream Products

• 1437300-17-8 dimethyl 2-((1-benzyl-4,5-dimethyl-1H-pyrrol-3-yl)methyl)-2-(but-2-yn-1-yl)malonate 
• 1437300-33-8 1-benzyl-4-(hex-4-yn-1-yl)-2,3-dimethyl-1H-pyrrole 
• 1437300-35-0 diethyl 2-((1-benzyl-4,5-dimethyl-1H-pyrrol-3-yl)methyl)-2-(but-2-yn-1-yl)malonate 
• 1437300-37-2 dibenzyl 2-((1-benzyl-4,5-dimethyl-1H-pyrrol-3-yl)methyl)-2-(but-2-yn-1-yl)malonate 
• 1437300-39-4 1-benzyl-4-((but-2-ynyloxy)methyl)-2,3-dimethyl-1H-pyrrole 
• 1437300-45-2 1-benzyl-2,3-dimethyl-4-(((3-(trimethylsilyl)prop-2-yn-1-yl)oxy)methyl)-1H-pyrrole 
• 1437300-43-0 dimethyl 2-((1-benzyl-4,5-dimethyl-1H-pyrrol-3-yl)methyl)-2-(3-(trimethylsilyl)prop-2-yn-1-yl)malonate 

Relevant articles and documents

Nickel-catalyzed [3 + 2] cycloaddition of diynes with methyleneaziridines via C-C bond cleavage

A Ni-catalyzed [3 + 2] cycloaddition via C-C bond cleavage of methyleneaziridines under mild conditions was developed. This reaction gave substituted pyrroles with excellent regioselectivity and a pendant alkyne unit, which is advantageous for further derivatization. The Royal Society of Chemistry 2013.

Observations on the ring opening reactions of 2-methyleneaziridines with acid chlorides and alkyl chloroformates

The ring-opening reactions of 2-methylene-aziridines with acid chlorides and alkyl chloroformates were studied. The mechanism suggested that the reactions proceeded by initial N-acylation to form corresponding aziridinium cation. This was followed by regiospecific ring opening by chloride ion at the sp3 hybridized aziridine carbon atom to produce the observed product.

A new synthesis of 2-methyleneaziridines

A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.