5619-07-8

Basic information

• Product Name: DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE
• Synonyms: METHYL 2-AMINO-3-PHENYLPROPANOATE HYDROCHLORIDE;TIMTEC-BB SBB003394;Methyl-d,1-phenylalanine hydrochloride;(±)-Phenylalanine methyl ester hydrochloride;DL-Phe-OMe hydrochloride;Methyl DL-phenylalaninate hydrochloride;DL-Phe-OMe HCl;H-DL-PHE-OME HCL
• CAS NO: 5619-07-8
• Molecular Formula: C₁₀H₁₄NO₂*Cl
• Molecular Weight: 215.68
• EINECS: 227-049-2
• Mol File: 5619-07-8.mol

Chemical Properties

• Melting Point: 158-162°C
• Boiling Point: 264.2 °C at 760 mmHg
• Flash Point: 126 °C
• Appearance: /
• Vapor Pressure: 0.00986mmHg at 25°C
• Storage Temp.: -15°C
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• Water Solubility: Slightly soluble in water.
• Sensitive: Hygroscopic
• BRN: 3597947
• CAS DataBase Reference: DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE(5619-07-8)
• EPA Substance Registry System: DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE(5619-07-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 5619-07-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE is used as an active pharmaceutical ingredient for the development of various medications. Its role in the synthesis of drugs and its potential therapeutic effects make it a valuable component in the creation of new pharmaceuticals.
Used in Food Industry:
DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE is used as a flavor enhancer and a building block for the synthesis of other flavor compounds in the food industry. Its ability to contribute to the taste and aroma of various food products makes it an important ingredient in the development of new and improved food items.

InChI:InChI=1/C10H13NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h2-6,9H,7,11H2,1H3;1H

Upstream product

• 100020-81-3 β-chloro-β-phenylalanine methyl ester hydrochloride 
• 90315-76-7 PChd-Phe-OMe 
• 69-96-5 Phenylserin 
• 100-52-7 benzaldehyde 
• 112792-62-8 trans-dichlorobis(dehydrophenylalanin-methylester)palladium(II) 
• 150-30-1 Phenylalanine 
• 67-56-1 methanol 
• 27172-85-6 phenylalanine methyl ester hydrochloride 
• 21132-20-7 (RS)-ethyl-2-acetamido-2-cyano-3-phenylpropanoate 
• 77-76-9 2,2-dimethoxy-propane 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 229485-67-0 β-chloro-β-phenylalanine 
• 112302-89-3 methyl 2-(N,N-dibenzylamino)-3-phenylpropanoate 

Downstream Products

• 4833-87-8 N-(N,N-phthaloyl-glycyl)-DL-phenylalanine-methyl ester 
• 41888-85-1 N-(N-benzyloxycarbonyl-glycyl)-DL-phenylalanine methyl ester 
• 17193-31-6 (R,S)-2-amino-3-phenylpropionamide 
• 122389-58-6 N-stearoyl-phenylalanine methyl ester 
• 97100-97-5 N-(N-formyl-valyl)-phenylalanine methyl ester; optically inactive substance 
• 24692-80-6 2-(2-Formylamino-4-methyl-pentanoylamino)-3-phenyl-propionic acid methyl ester 
• 141635-23-6 2-(Methoxyoxalyl-amino)-3-phenyl-propionic acid methyl ester 
• 96017-08-2 2-(1-Oxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionic acid methyl ester 
• 83851-72-3 2-thenoyl-DL-Phe-OMe 
• 83851-78-9 (5-bromo-2-thenoyl)-DL-Phe-OMe 
• 107326-52-3 2-[Bis-(3-methyl-but-3-enyl)-amino]-3-phenyl-propionic acid methyl ester 
• 83851-86-9 (5-nitro-2-thenoyl)-DL-Phe-OMe 
• 69358-28-7 ethyl 3‐((2‐benzyl‐3‐methoxy‐3‐oxopropyl)amino)‐3‐oxopro‐panoate 
• 127750-60-1 N-cinnamoyl-D,L-phenylalanine methyl ester 

Relevant articles and documents

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

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Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Chiral polycyclic tropane compound as well as preparation method and application thereof

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Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines

Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.

Bioinspired Radical Stetter Reaction: Radical Umpolung Enabled by Ion-Pair Photocatalysis

A bioinspired, intermolecular radical Stetter reaction of α-keto acids and aldehydes is disclosed that is contingent on a formal “radical umpolung” concept. Enabled by secondary amine activation, electrostatic recognition ensures that the α-ketocarboxylic acids, which function as latent acyl radicals, are proximal to the in situ generated iminium salts. This photoactive contact ion pair is an electron donor–acceptor (EDA) complex, and undergoes facile single electron transfer (SET) and rapid decarboxylation prior to radical–radical recombination. Importantly, decarbonylation is mitigated by this strategy. The initial computational validation on which the process is predicated matches closely with experiment. Synergising organo- and photocatalysis activation principles finally expands the mechanistic and synthetic scope of the classic Stetter reaction to include α,β-unsaturated aldehydes as acceptors.

Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates

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Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

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A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids

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A PRODUCING METHOD OF D-FORM OR L-FORM AMINO ACID DERIVATIVES HAVING A THIOL GROUP

This invention provides a producing method of an optical active D-form and/or L-form amino acid having a thiol group on its side chain by a simple method with good yield. This invention provides a producing method of an amino acid derivative having a thiol group on its side chain, and an intermediate thereof, wherein the producing method is characterized by producing an intermediate composition comprising a D-form and L-form of amino acid derivate having a thiol group at β -position, reacting D- or L-amino acid selective hydrolytic enzyme, and isolating the hydrolyzed D- or L-amino acid derivative.

Asymmetric chemoenzymatic synthesis of N-acetyl-α-amino esters based on lipase-catalyzed kinetic resolutions through interesterification reactions

Several phenylalanine analogs have been synthesized through a four-step route starting from easily available ethyl acetamidocyanoacetate. In a first reaction, and making use of phase transfer catalysts, this compound reacted with several alkyl halides, being benzyltributylammonium chloride identified as the best one for the production of a series of quaternary amino acids in moderate to excellent yields (52-95%). Then, the corresponding N-acetyl-phenylalanine methyl and allyl ester derivatives were obtained through acidic hydrolysis, esterification, and N-acetylation. Rhizomucor miehei lipase was found as a versatile enzyme for the resolution of these amino esters, finding the best results through interesterification reactions with butyl butyrate in acetonitrile. A great influence in the stereoselectivity was found depending on the chemical structure of the compound, achieving for the non- or para-substituted in the phenyl ring excellent stereoselectivities, being moderate for the meta-nitro derivative, while the ortho-nitro amino ester did not react.