21161-20-6

Basic information

• Product Name: 2-Azetidinone, 4-(4-chlorophenyl)-
• CAS NO: 21161-20-6
• Molecular Formula: C9H8ClNO
• Molecular Weight: 181.622
• Mol File: 21161-20-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 4-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-(4-chlorophenyl)-(21161-20-6)
• EPA Substance Registry System: 2-Azetidinone, 4-(4-chlorophenyl)-(21161-20-6)

Safety Data

• Hazardous Substances Data: 21161-20-6(Hazardous Substances Data)

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 269716-25-8 1-chloro-2-(trimethylsilyl)oxy-3-aza-4-p-chloro-phenyl-1,3-butadiene 
• 85654-07-5 N-(4-chlorobenzylidene)-N-(1,1,1-trimethylsilyl)amine 
• 104-88-1 4-chlorobenzaldehyde 
• 19947-39-8 3-amino-3-(4-chlorophenyl)propionic acid 
• 566198-11-6 (+/-)-trimethylsilyl β-(N-trimethylsilylamino)-β-(4-chlorophenyl)propionate 

Downstream Products

• 930769-49-6 (S)-4-(4-chlorophenyl)-2-azetidinone 
• 1350930-30-1 C₁₃H₁₄ClNO₂ 
• 1402941-74-5 4-(4-chlorophenyl)azetidine-2-thione 
• 948027-08-5 C₉H₈ClNO 
• 18166-64-8 4-chlorocinnamide 
• 22101-09-3 3-(4-chlorophenyl)-3-phenylpropionamide 
• 7474-19-3 3,3-diphenylpropionamide 
• 930769-55-4 (S)-3-Amino-3-(4-chloro-phenyl)-propionic acid; hydrochloride 

Relevant articles and documents

Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines

The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry of this class of four-membered heterocycles. Two unexpected and unprecedented results have been observed: an "ortho-effect" accounting for the regioselective functionalization of the azetidine ring, and self-condensation leading to new and interesting azetidine-based peptidomimetics.

A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams

A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).

A trans-stereoselective synthesis of 3-halo-4-alkyl(aryl)-NH-azetidin-2-ones

Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting β-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidino