27593-61-9

Basic information

• Product Name: Carbamic acid, (phenylmethylene)-, methyl ester
• Synonyms: methyl N-phenylmethylenecarbamate;N-benzylidene methyl carbamate;Carbamic acid,(phenylmethylene)-,methyl ester;benzaldehyde N-carbomethoxy-imine;methyl benzylidenecarbamate;N-methoxycarbonylbenzaldimine
• CAS NO: 27593-61-9
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.176
• Mol File: 27593-61-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (phenylmethylene)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (phenylmethylene)-, methyl ester(27593-61-9)
• EPA Substance Registry System: Carbamic acid, (phenylmethylene)-, methyl ester(27593-61-9)

Safety Data

• Hazardous Substances Data: 27593-61-9(Hazardous Substances Data)

Upstream product

• 134920-16-4 N-methoxycarbonyl-3-phenyloxaziridine 
• 121-44-8 triethylamine 
• 603-35-0 triphenylphosphine 
• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 598-55-0 methyl carbamate 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 79-22-1 methyl chloroformate 
• 100-52-7 benzaldehyde 
• 774-48-1 (diethoxymethyl)benzene 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 27593-56-2 methyl N-(1-ethoxy-1-phenylmethyl)carbamate 

Downstream Products

• 127941-21-3 (2R,6R)-4-(2-Benzyloxy-ethyl)-2,6-diphenyl-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 27593-56-2 methyl N-(1-ethoxy-1-phenylmethyl)carbamate 
• 141178-32-7 methyl N-(1-phenylpropyl)carbamate 
• 53842-74-3 methyl L-N-(benzylidene)valil-L-leucinate 
• 13803-83-3 methyl (S)-2-(benzylideneamino)-3-methylbutanoate 
• 538-51-2 benzylidene phenylamine 

Relevant articles and documents

Asymmetric allylboration of acyl imines catalyzed by chiral diols

Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3′-Ph2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) are obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asymmetric transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic investigations of the allylboration reaction including IR, NMR, and mass spectrometry studies indicate that acyclic boronates are activated by chiral diols via exchange of one of the boronate alkoxy groups with activation of the acyl imine via hydrogen bonding.

Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: Use of phenyldiazomethane, diazoesters and diazoacetamides

Imine aziridination using diazo-compounds and catalytic quantities of metal salts and sulfides has been investigated. A range of imines derived from benzaldehyde bearing electron-withdrawing groups (N-Ts,N-SO2CH2CH2SiMesu

Electrophilic Amination: Preparation and Use of N-Boc-3-(4-cyanophenyl)oxaziridine, a New Reagent That Transfers a N-Boc Group to N- and C-Nucleophiles

We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b.Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Nβ-Boc-hydrazines) and enolates (to give N-Boc-amino drivatives).