54912-92-4

Basic information

• Product Name: S-phenyl 1-tert-butylaziridine-2-carbothioate
• CAS NO: 54912-92-4
• Molecular Formula: C₁₃H₁₇NOS
• Molecular Weight: 235.3452
• Mol File: 54912-92-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 323.2°C at 760 mmHg
• Flash Point: 149.3°C
• Density: 1.14g/cm³
• Vapor Pressure: 0.000266mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: S-phenyl 1-tert-butylaziridine-2-carbothioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-phenyl 1-tert-butylaziridine-2-carbothioate(54912-92-4)
• EPA Substance Registry System: S-phenyl 1-tert-butylaziridine-2-carbothioate(54912-92-4)

Safety Data

• Hazardous Substances Data: 54912-92-4(Hazardous Substances Data)

Upstream product

• 25662-14-0 methyl 1-tert-butylaziridine-2-carboxylate 
• 108-98-5 thiophenol 

Downstream Products

• 109849-73-2 rac-S-phenyl 1-(tert-butyl)-2-(2-nitro-1-phenylethyl)aziridine-2-carbothioate 
• 109849-72-1 rac-1-(tert-butyl)-6-phenyl-1-aza-5-oxaspiro<2,3>-hexan-4-one 
• 109849-70-9 rac-S-phenyl u-1-(tert-butyl)-2-(α-hydroxybenzyl)aziridine-2-carbothioate 
• 109849-70-9 rac-S-phenyl l-1-(tert-butyl)-2-(α-hydroxybenzyl)aziridine-2-carbothioate 
• 109849-68-5 rac-S-phenyl 1-(tert-butyl)-2-(1-hydroxyethyl)aziridine-2-carbothioate 
• 109849-75-4 rac-S-phenyl 1-(tert-butyl)-2-methylaziridine-2-carbothioate 

Relevant articles and documents

Preparation and C-Alkylation of Enantiomerically Pure S-Phenyl Aziridenecarbothioates. On the Structure of Small-Ring Ester Lithium Enolates

Racemic and enantiomerically pure methyl N-(tert-butyl)-N-benzyl- and N-1-(phenylethyl)aziridinecarboxylates are prepared by known methods and converted to phenyl thioesters (1, 2, 15, 16; Schemes 2 and 3).These are deprotonated with lithium diisopropylamide (LDA) and BuLi (for removal of diisopropylamine) in THF at dry-ice temperature.The resulting lithiated species are surprizingly stable and deuterated, alkylated (CH3, C2H5, allyl, benzyl), and added to aldehydes and nitroolefins in good yields (50-80 percent, 18 examples; Schemes 1 and 4-6).The configurational stability of the lithiated species is studied, and conclusions about their structures are drown.Thus, a C(α)-lithiated ester (see L, Scheme 9) or an O-liithia1ed "enolate" (see M) with pyramidalized C(β)-atom is proposed for species from levorotatory S-phenyl N-benzylaziridinecarbothioate which does not undergo racemization after 1 h at -60 deg C (THF solution).