2283-42-3

Basic information

• Product Name: 3-methylphenylalanine
• Synonyms: 3-METHYLPHENYLALANINE
• CAS NO: 2283-42-3
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.2157
• Mol File: 2283-42-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 322.8°C at 760 mmHg
• Flash Point: 149°C
• Density: 1.165g/cm³
• Vapor Pressure: 0.000112mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 3-methylphenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylphenylalanine(2283-42-3)
• EPA Substance Registry System: 3-methylphenylalanine(2283-42-3)

Safety Data

• Hazardous Substances Data: 2283-42-3(Hazardous Substances Data)

Upstream product

• 60-29-7 diethyl ether 
• 872270-42-3 2-azidocarbonyl-3-m-tolyl-propionic acid 
• 61676-25-3 2-oxo-3-m-tolyl-propionic acid 
• 3029-79-6 (E)-3-methylcinnamic acid 
• 5472-70-8 3-methyl-phenylalanine 
• 620-23-5 m-tolyl aldehyde 
• 68208-17-3 (R,S)-3-amino-3-(3-methylphenyl)propionic acid 
• 3029-79-6 3-methylcinnamic acid 
• 620-13-3 1-bromomethyl-3-methyl-benzene 
• 145243-34-1 2-(Benzhydrylidene-amino)-3-m-tolyl-propionic acid methyl ester 
• 72615-63-5 α-benzoylamino-3-methyl-cinnamic acid 
• 5440-54-0 acetylamino-(3-methyl-benzyl)-malonic acid diethyl ester 

Downstream Products

• 225120-37-6 (S)-N-(1-((cyanomethyl)amino)-1-oxo-3-(m-tolyl)propan-2-yl)-3-(trifluoromethyl)benzamide 
• 167217-14-3 methyl (S)-2-amino-3-(m-tolyl)propanoate 
• 374119-33-2 (R)-2-hydroxy-3-(3-methylphenyl)-propionic acid 

Relevant articles and documents

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One-Pot Enzymatic Synthesis of d-Arylalanines Using Phenylalanine Ammonia Lyase and l-Amino Acid Deaminase

The phenylalanine ammonia-lyase (AvPAL) from Anabaena variabilis catalyzes the amination of substituent trans-cinnamic acid (t-CA) to produce racemic d,l-enantiomer arylalanine mixture owing to its low stereoselectivity. To produce high optically pure d-arylalanine, a modified AvPAL with high d-selectivity is expected. Based on the analyses of catalytic mechanism and structure, the Asn347 residue in the active site was proposed to control stereoselectivity. Therefore, Asn347 was mutated to construct mutant AvPAL-N347A, the stereoselectivity of AvPAL-N347A for d-enantiomer arylalanine was 2.3-fold higher than that of wild-type AvPAL (WtPAL). Furthermore, the residual l-enantiomer product in reaction solution could be converted into the d-enantiomer product through stereoselective oxidation by PmLAAD and nonselective reduction by reducing agent NH3BH3. At optimal conditions, the conversion rate of t-CA and optical purity (enantiomeric excess (eeD)) of d-phenylalanine reached 82% and exceeded 99%, respectively. The two enzymes displayed activity toward a broad range of substrate and could be used to efficiently synthesize d-arylalanine with different groups on the phenyl ring. Among these d-arylalanines, the yield of m-nitro-d-phenylalanine was highest and reached 96%, and the eeD exceeded 99%. This one-pot synthesis using AvPAL and PmLAAD has prospects for industrial application.

Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines

With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.