23044-57-7

Basic information

• Product Name: N-[(3E)-1-tert-butyl-2-methyldiaziridin-3-ylidene]-2-methylpropan-2-amine
• Synonyms: 2-propanamine, N-[1-(1,1-dimethylethyl)-2-methyl-3-diaziridinylidene]-2-methyl-; N-(1-tert-Butyl-2-methyldiaziridin-3-ylidene)-2-methylpropan-2-amine
• CAS NO: 23044-57-7
• Molecular Formula: C₁₀H₂₁N₃
• Molecular Weight: 183.2938
• Mol File: 23044-57-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 203.6°C at 760 mmHg
• Flash Point: 77°C
• Density: 0.93g/cm³
• Vapor Pressure: 0.275mmHg at 25°C
• Refractive Index: 1.491
• PKA: 12.95±0.20(Predicted)
• CAS DataBase Reference: N-[(3E)-1-tert-butyl-2-methyldiaziridin-3-ylidene]-2-methylpropan-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(3E)-1-tert-butyl-2-methyldiaziridin-3-ylidene]-2-methylpropan-2-amine(23044-57-7)
• EPA Substance Registry System: N-[(3E)-1-tert-butyl-2-methyldiaziridin-3-ylidene]-2-methylpropan-2-amine(23044-57-7)

Safety Data

• Hazardous Substances Data: 23044-57-7(Hazardous Substances Data)

Upstream product

• 1189055-47-7 N',N-di(tert-butyl)-N-methyl-N-hydroxyguanidine O-sulfonic acid 

Downstream Products

• 691-24-7 1,3-di-tert-butylcarbodiimide 
• 100-97-0 hexamethylenetetramine 

Relevant articles and documents

Syntheses and15N NMR Spectra of Iminodiaziridines - Ring-Expansions of 1-Aryl-3-iminodiaziridines to 1H- and 3aH-Benzimidazoles, 2H-Indazoles, and 5H-Dibenzo[d,f] [1,3]diazepines

Iminodiaziridines are synthesized, by (i) 1,3-dehydrochlorination with potassium, teri-butoxide of N-chloroguanidines, generated in situ from. N,N′,N″-substituted guanidines with tert-butyl hypochlorite, and (ii) base-mediated 1,3-elimination of sulfuric acid from N,N',N″- substituted hydroxyguanidine O-sulfonic acids. At elevated temperatures, (alkylimino)diaziridines undergo valence isomerization by 1,3shift, [2+1] cycloelimination to afford isocyanides and diazenes, and ring-opening elimination to yield alkylideneguanidines. N′-Aryl-N-hydroxyguanidine O-sulfonic acids furnish (N-arylimino)diaziridines, but no 1-aryl-3- iminodiaziridines, instead giving rearranged isomere. Precursors containing perdeuterated feri-butyl groups give rearranged products that show complete scrambling. This indicates that l-aryl-3iminodiaziridines are intermediates that undergo very rapid I degenerate valence isomerization. Provided that the ortho aryl positions are substituted, high yields of (arylimino)diaziridines are obtained, along with 2-imino-2,3-dihydro-3aHbenzimidazoles, Otherwise, 2-amino-lH-benzimidazoles and strongly fluorescent 3-amino-2H-indazoles, originating from rearrangements of the elusive l-aryl-3-iminodiaziridines, predominate. N',N″-Diaryl-N-hydroxyguanidine O-sulfonic acids give only rearranged products: a 2-amino-1H-benzimidazole and a 6-amino-5H-dibenzo[d,f][1. 3]diazepine if aryl = phenyl, or a 2-imino-2,3-dihydro-3aH-benzimidazole if aryl = mesityl. 3aH-Benzimidazoles slowly dimerize through Diels-Alder reactions. 15N NMR signals were assigned, to the syn and anti ring nitrogen atoms of iminodiaziridines with the help of a combination of homonuclear NOE and HNHMBC or HN-gHMBC experiments.