104597-98-0

Basic information

• Product Name: 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE
• Synonyms: 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE;(S)-1-benzyl 2-methyl aziridine-1,2-dicarboxylate;Methyl (S)-(-)-N-Z-aziridine-2-carboxylate;Methyl (S)-(-)-N-benzyloxycarbonylaziridine-2-carboxylate;(S)-N-[(Benzyloxy)carbonyl]aziridine-2-carboxylic Acid Methyl Ester;Methyl (S)-(-)-N-Z-aziridine-2-carboxylate 96%;1-benzyl 2-methyl (S)-aziridine-1,2-dicarboxylate
• CAS NO: 104597-98-0
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.24
• Product Categories: Aziridines;Chiral Building Blocks;Organic Building Blocks
• Mol File: 104597-98-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 160-165 °C2 mm Hg(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.04E-05mmHg at 25°C
• Refractive Index: n20/D 1.519(lit.)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Soluble), Dichloromethane
• PKA: -5.65±0.40(Predicted)
• CAS DataBase Reference: 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE(104597-98-0)
• EPA Substance Registry System: 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE(104597-98-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 104597-98-0(Hazardous Substances Data)

Usage

Description

Methyl (S)-(–)-N-Z-aziridine-2-carboxylate is a chiral building block that is commonly used in the organic stereoselective synthesis of various compounds, including anticancer agents, antibiotics, and enzyme inhibitors.

Uses

Like aziridine carboxylic acid ester derivative, (S)-1-Benzyl 2-methyl aziridine-1,2-dicarboxylate can be used for the synthetic application of chiral aziridine via esterification.

InChI:InChI=1/C12H13NO4/c1-16-11(14)10-7-13(10)12(15)17-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3/t10-,13?/m0/s1

Upstream product

• 75154-69-7 (S)-methyl aziridine-2-carboxylate 
• 501-53-1 benzyl chloroformate 
• 67-56-1 methanol 
• 1314042-77-7 (4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole 
• 64420-86-6 O-p-toluenesulfonyl benzyloxyhydroxamate 
• 107-02-8 acrolein 
• 75154-68-6 methyl (2S)-N-tritylaziridine-2-carboxylate 

Downstream Products

• 2717-76-2 (S)-N-benzyloxycarbonyl-L-tryptophan methyl ester 
• 126496-83-1 (S)-2-Benzyloxycarbonylamino-3-(5-methoxy-1H-indol-3-yl)-propionic acid methyl ester 
• 126496-88-6 (S)-2-{[3-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-7-hexyl-1H-indol-4-yl]-methyl-amino}-3-methyl-butyric acid methyl ester 
• 1017238-28-6 (S)-methyl 2-{[(benzyloxy)carbonyl]amino}-3-(6-methoxy-1H-indol-3-yl)propanoate 
• 75154-69-7 (S)-methyl aziridine-2-carboxylate 

Relevant articles and documents

Synthesis of homochiral acyclic mono- and bis(α-amino acid)s with oligo(oxyethylene) chains

Synthesis of homochiral α-amino acids 3a-3e and bis(α-amino acid)s 4a-4e via BF3·Et2O-catalyzed ring-opening of methyl (S)-1-[(benzyloxy)carbonyl]aziridine-2-carboxylate (7) with oligo(ethylene glycol)s and subsequent acid hydrolysis

Selective cleavage of carbamate protecting groups from aziridines with otera's catalyst

Otera's distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selec

Catalytic asymmetric aziridination of α,β-unsaturated aldehydes

The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziri