1074-42-6

Basic information

• Product Name: 1-benzylaziridine
• Synonyms: 1-benzylaziridine;1-(Phenylmethyl)aziridine
• CAS NO: 1074-42-6
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• Mol File: 1074-42-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 179.3°Cat760mmHg
• Flash Point: 54.7°C
• Appearance: /
• Density: 1.086g/cm³
• Vapor Pressure: 0.95mmHg at 25°C
• Refractive Index: 1.6
• PKA: 6.85±0.20(Predicted)
• CAS DataBase Reference: 1-benzylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzylaziridine(1074-42-6)
• EPA Substance Registry System: 1-benzylaziridine(1074-42-6)

Safety Data

• Hazardous Substances Data: 1074-42-6(Hazardous Substances Data)

Usage

General Description

1-benzylaziridine is a chemical compound that is a type of organic compound containing a six-membered nitrogen-containing cycle. It is also known as N-benzylaziridine and has the chemical formula C9H13N. 1-benzylaziridine is commonly used as a precursor in organic synthesis, especially in the production of various pharmaceuticals and agrochemicals. It is a versatile building block in organic chemistry and can be easily modified to create new compounds with diverse properties. The compound is also known to have potential application as a chiral auxiliary in asymmetric synthesis. Additionally, 1-benzylaziridine is a stable, colorless liquid at room temperature, and its handling and storage generally require standard precautions for working with organic chemicals.

InChI:InChI=1/C9H11N/c1-2-4-9(5-3-1)8-10-6-7-10/h1-5H,6-8H2

Upstream product

• 104-63-2 N-Benzylethanolamine 
• 17886-25-8 1-benzyl-4,5-dihydro-1H-[1,2,3]triazole 
• 100-52-7 benzaldehyde 
• 2133-07-5 2-(benzylamino)ethyl hydrogen sulfate 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 100-39-0 benzyl bromide 
• 100-46-9 benzylamine 
• 122079-50-9 N-benzyloxazolidin-5-one 
• 17136-36-6 N-benzylglycine 
• 33538-02-2 N-(2-bromoethyl)benzylammonium bromide 
• 1972-28-7 diethylazodicarboxylate 
• 104143-95-5 3-benzyl-5-phenyl-1,3-oxazolidine 
• 151-56-4 ethyleneimine 
• 100-44-7 benzyl chloride 

Downstream Products

• 6772-61-8 2-(4-benzylphenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 1034-11-3 N,N'-dibenzylpiperazine 
• 578-66-5 8-amino quinoline 
• 735351-82-3 2-benzyl-6-bromo-3,4-dihydroisoquinolin-1(2H)-one 
• 808141-26-6 2-benzyl-7-chloro-3,4-dihydro-2H-isoquinolin-1-one 

Relevant articles and documents

Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines

A nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines has been disclosed. The current strategy provides direct access to benzolactams by the C-H alkylation-intramolecular amidation cascade event with the concomitant removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines can be controlled by the substituents. The reaction with chiral aziridines proceeds with inversion of configuration, thus suggesting an SN2-type nucleophilic ring-opening pathway.

Observations on the modified wenker synthesis of aziridines and the development of a biphasic system

A cheap and reliable process for the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions for a range of amino alcohol starting materials. A 100 mmol "one-pot" process has also been devised, and the enantiopurity of the starting amino alcohol is retained in the aziridine product.

Preparation of N-arylmethyl aziridine derivatives, 1,4,7,10-tetraazacyclododecane derivatives obtained therefrom and N-arylmethyl-ethanol-amine sulphonate esters as intermediates

PCT No. PCT/GB96/00552 Sec. 371 Date Dec. 2, 1997 Sec. 102(e) Date Dec. 2, 1997 PCT Filed Mar. 8, 1996 PCT Pub. No. WO96/28420 PCT Pub. Date Sep. 19, 1996Aziridines may be subjected to a cyclooligomerization reaction to produce polyazacycloalkane compounds useful for example in the preparation of chelating agents for use in diagnostic imaging contrast agents. N-benzyl-aziridine in particular is useful as it can be cyclotetramerized and debenzylated to yield cyclen, a key intermediate in chelating agent preparation. The invention provides a particularly attractive route to production of N-benzyl and other N-arylmethyl aziridines of formula (I) where each R1 is independently hydrogen or a group AR and Ar is an optionally substituted phenyl group. The process comprises reacting a purified N-arylmethylethanolaminesulphonate ester with a base. N-arylmethyl-ethanolamine sulphonate ester of the formula R'NHCH2CH2OSO3H, wherein the N-arylmethyl group R' is an N-(bisarylmethyl) or N-(triarylmethyl) group, as intermediates. In a further aspect, the invention provides compounds of formula (II) where Ar and R1 are as hereinabove defined and at least two differing ArCHR21 moieties are present.