13200-85-6

Basic information

• Product Name: N-FORMYL-L-PHENYLALANINE
• Synonyms: FOR-PHENYLALANINE;FOR-PHE-OH;FORMYL-L-PHENYLALANINE;N-FORMYL-L-PHENYLALANINE;N-FORMYL-L-PHENYLALNANINE;N-FORMYL-PHENYLALANINE;N-formyl-3-phenyl-L-alanine;(S)-α-(Formylamino)benzenepropionic acid
• CAS NO: 13200-85-6
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• EINECS: 236-166-8
• Product Categories: A - H;Amino Acids;Modified Amino Acids
• Mol File: 13200-85-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 165°C
• Boiling Point: 449.7 °C at 760 mmHg
• Flash Point: 225.8 °C
• Appearance: /
• Density: 1.235g/cm³
• Vapor Pressure: 7.11E-09mmHg at 25°C
• Refractive Index: 74 ° (C=4, EtOH)
• Storage Temp.: −20°C
• CAS DataBase Reference: N-FORMYL-L-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-FORMYL-L-PHENYLALANINE(13200-85-6)
• EPA Substance Registry System: N-FORMYL-L-PHENYLALANINE(13200-85-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 13200-85-6(Hazardous Substances Data)

Usage

Definition

ChEBI: An N-acyl-L-phenylalanine that is L-phenylalanine in which one of the hydrogens of the amino group has been replaced by a formyl group.

InChI:InChI=1/C10H11NO3/c12-7-11-9(10(13)14)6-8-4-2-1-3-5-8/h1-5,7,9H,6H2,(H,11,12)(H,13,14)/t9-/m0/s1

Upstream product

• 5856-63-3 (2R)-2-aminobutan-1-ol 
• 4289-95-6 N-formyl-phenylalanine 
• 63-91-2 L-phenylalanine 
• 2258-42-6 formyl acetic anhydride 
• 63-91-2 L-phenylalanine 
• 113388-44-6 (formyloxy)(acetoxy)phenylmethane 
• 2311-21-9 N-formyl-L-phenylalanine-methylester 
• 77287-34-4 formamide 
• 150-30-1 Phenylalanine 
• 64-18-6 formic acid 
• 131348-01-1 (1S)-endo-fenchylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 101783-14-6 N-(N-formyl-phenylalanyl)-glycine anilide 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 4172-32-1 N-(N-formyl-DL-phenylalanyl)-glycine ethyl ester 
• 3480-79-3 N-formyl-L-phenylalanine cyanomethyl ester 
• 4172-32-1 N-formyl-L-phenylalanylglycine ethyl ester 
• 5249-47-8 N-Formyl-L-phenylalanin-<2>naphthylamid 
• 35858-71-0 N-Formyl-L-phenylalanin-methylhydrazid 
• 35742-76-8 N-Formyl-L-phenylalanin-formylhydrazid 
• 100135-64-6 N-formyl-L-phenylalanylglycine 
• 69231-09-0 (-)-(2S)-2-(formylamino)-3-phenyl-1-propanol 
• 1126921-70-7 (S)-2-formylamino-3-phenyl-N-((S)-1-phenyl-ethyl)-propionamide 
• 1057856-46-8 (S)-2-formylamino-3-phenyl-propionic acid 1-((2S,3S,4S)-3-hexyl-4-oxo-oxetan-2-ylmethyl)-hex-4-enyl ester 
• 1057856-42-4 (S)-2-formylamino-3-phenyl-propionic acid 1-((2S,3S,4S)-3-hexyl-4-oxo-oxetan-2-ylmethyl)-tetradecyl ester 
• 130106-84-2 (S)-2-formylamino-3-phenyl-propionic acid 1-((2S,3S,4S)-3-hexyl-4-oxo-oxetan-2-ylmethyl)-pent-4-enyl ester 

Relevant articles and documents

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Solvent dependency though not solvate formation in the derivative-derivative resolution of N-formylphenylalanine

The efficiency of the resolution of N-formylphenylalanine was remarkably improved using (S)-(+)-2-benzylaminobutanol resolving agent in acetone. The efficiency of the resolution strongly depended on the quality of the solvent. Nevertheless, solvate formation did not occur during the process. The nature of the solvent-dependence was studied. The solid-melt binary phase diagram of the diastereomeric salts formed during the resolution by (S)-(+)-2-benzylaminobutanol was measured and discussed. It was recognized that the (S)-(+)-benzylaminobutanol (S)-(+)-N-formylphenylalanine salt exists in two polymorphic modifications. The effect of structurally related chiral and achiral auxiliary reagents in the above resolution was also studied. Thus, (S)-(+)-2-benzylaminobutanol was applied together with an (R)-(+)-1-phenylethylamine auxiliary resolving agent and benzylamine was used as a half-equivalent achiral basic reagent in a Pope-Peachey type resolution of N-formylphenylalanine by (S)-(+)-2-benzylaminobutanol. The results are compared to those obtained by the structurally related (R)-(+)-1-phenylethylamine chiral auxiliary.

THE FORMYLATION OF AMINO ACIDS WITH ACETIC FORMIC ANHYDRIDE.

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An aryne-based three-component access to α-aroylamino amides

Aryne chemistry has recently received widespread attention and isocyanides have been reported as efficient nucleophilic partners in a set of multicomponent transformations. In this study, we demonstrate that tertiary α-monosubstituted α-isocyanoacetamides are efficaciously coupled with water and benzyne to offer a direct and metal-free access to densely functionalized α-benzoylamino amides, without competing with the intramolecular cyclization to 5-aminooxazoles. Despite the formation of the aryl anion as a key intermediate, the reaction displays a stereoconservative course, allowing for the preparation of enantiomerically pure α-benzoylamino amides. Finally, the synthetic utility of the reported MCR was exemplified by the preparation of proglumide, a cholecystokinin antagonist.

MgI2-chemoselective cleavage for removal of amino acid protecting groups: A fresh vision for peptide synthesis

In the field of peptide synthesis, the key to a successful access to synthetic targets lies on a pertinent combination of protecting groups. Their choice is directed by their selective removal conditions. We present here the behavior of some of the most used protecting groups in peptide chemistry under experimental cleavage conditions, combining MgI2 with MW irradiation, using 2-Me-THF as a green solvent. In these experimental conditions, the benzyloxycarbonyl protecting group as well as the Merrifield resin can be re-considered in peptide chemistry.