59200-38-3

Basic information

• Product Name: D-Phenylalanine, N-formyl-, methyl ester
• Synonyms: N-Formyl-D-phenylalaninmethylester;CHO-D-Phe-OMe;N-formyl-(S)-phenylalanine methyl ester;(R)-2-Formylamino-3-phenyl-propionic acid methyl ester;N-formyl-D-phenylalanine methyl ester;2-(formamido)-3-phenylpropionic acid acid methyl ester
• CAS NO: 59200-38-3
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Mol File: 59200-38-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 175 - 180 °C (21.8 mmHg)
• CAS DataBase Reference: D-Phenylalanine, N-formyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Phenylalanine, N-formyl-, methyl ester(59200-38-3)
• EPA Substance Registry System: D-Phenylalanine, N-formyl-, methyl ester(59200-38-3)

Safety Data

• Hazardous Substances Data: 59200-38-3(Hazardous Substances Data)

Upstream product

• 21685-51-8 D-phenylalanine methyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 149-73-5 trimethyl orthoformate 
• 196207-83-7 4-methoxycarbonyl-5-phenyl-2-oxazoline 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 65638-74-6 (Z)-N-Formyldehydrophenylalanin-methylester 
• 150760-95-5 formic acid cyanomethyl ester 

Downstream Products

• 112790-04-2 2-isocyano-3-phenylpropionic acid methyl ester 

Relevant articles and documents

TBSOTf-promoted versatile N-formylation using DMF at room temperature

Hydrazides and amines were N-formylated by DMF in the presence of tert-butyldimethylsilyl triflate (TBSOTf) at room temperature, in good to excellent yields.

Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands

Enantioselectivities up to >99% ee were achieved in the rhodium-catalyzed asymmetric hydrogenation of N-formyl dehydroamino esters using monodentate phosphoramidites as chiral ligands. The substrates were synthesized by condensation of methyl isocyanoacetate with a range of aldehydes and with cyclohexanone. A highly convenient multigram scale one step synthesis of methyl 2-(formamido)acrylate was developed. This compound was used in the synthesis of methyl 2-(formamido)cinnamate via a solvent free Heck reaction. Moreover, full conversion and >99% ee were obtained in 1 h in the hydrogenation of methyl 2-(formamido)acrylate with 0.2 mol% catalyst and 2 bar hydrogen pressure. The versatility of the formyl protection was established by its removal under mild conditions.

Formyloxy-acetonitrile - A reagent for convenient N- and O-formylations

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