5472-70-8

Basic information

• Product Name: 2-AMINO-3-M-TOLYL-PROPIONIC ACID
• Synonyms: 2-AMINO-3-M-TOLYL-PROPIONIC ACID;DL-3-METHYLPHENYLALANINE;3-Methy-DL-Phenylalanine;DL-3-Me-Phe-OH;3- Methylphenylalanine(3-Methylphe);Nsc29447;3-Methyl-DL-phenylalanine;2-AMINO-3-M-TOLYL-PR
• CAS NO: 5472-70-8
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Mol File: 5472-70-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 245℃
• Boiling Point: 567.2 °C at 760 mmHg
• Flash Point: 296.8°C
• Appearance: /
• Density: 1.165
• Vapor Pressure: 6.99E-13mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.22±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-3-M-TOLYL-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-M-TOLYL-PROPIONIC ACID(5472-70-8)
• EPA Substance Registry System: 2-AMINO-3-M-TOLYL-PROPIONIC ACID(5472-70-8)

Safety Data

• Hazardous Substances Data: 5472-70-8(Hazardous Substances Data)

Usage

General Description

2-Amino-3-M-Tolyl-Propionic Acid, also known as alpha-amino-3-m-tolylpropionic acid, is a chemical compound with the molecular formula C10H13NO2. It exists as a solid substance and finds its use in the field of organic synthesis. The compound consists of an alpha amino group (NH2), a phenyl group substituted with a methyl group (3-M-Tolyl), and a carboxylic acid group (COOH) attached to a three-carbon aliphatic chain. 2-AMINO-3-M-TOLYL-PROPIONIC ACID is often used in the production of other chemicals such as pharmaceuticals and can be used as an intermediate during these synthesis processes.

InChI:InChI=1/C20H18N2O2/c23-19-13-8-4-5-9-14(13)20-18-16(22-24-20)11-10-15(17(18)19)21-12-6-2-1-3-7-12/h4-5,8-12,21H,1-3,6-7H2

Upstream product

• 2283-42-3 (S)-2-amino-3-(3-methylphenyl)propionic acid 
• 72615-63-5 α-benzoylamino-3-methyl-cinnamic acid 
• 145243-34-1 2-(Benzhydrylidene-amino)-3-m-tolyl-propionic acid methyl ester 
• 60-29-7 diethyl ether 
• 872270-42-3 2-azidocarbonyl-3-m-tolyl-propionic acid 
• 620-13-3 1-bromomethyl-3-methyl-benzene 
• 620-23-5 m-tolyl aldehyde 
• 5440-54-0 acetylamino-(3-methyl-benzyl)-malonic acid diethyl ester 

Downstream Products

• 748128-33-8 (R)-3-amino-3-(3-methyl-phenyl)-propionic acid 
• 114926-39-5 (R)-2-amino-3-(3-methylphenyl)propionic acid 
• 2283-42-3 (S)-2-amino-3-(3-methylphenyl)propionic acid 

Relevant articles and documents

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.

Enhanced conversion of racemic α-arylalanines to (R)-β- arylalanines by coupled racemase/aminomutase catalysis

(Graph Presented) The Taxus phenylalanine aminomutase (PAM) enzyme converts several (S)-α-arylalanines to their corresponding (R)-β- arylalanines. After incubating various racemic substrateswith 100 μg of PAM for 20 h at 31°C, each (S)-α-arylalanine was enantioselectively isomerized to its corresponding (R)-β-product. With racemic starting materials, the ratio of (R)-β-arylalanine product to the (S)-α-substrate ranged between 0.4 and 1.8, and the remaining nonproductive (R)-α-arylalanine became enriched. To utilize the (R)-α-isomer, the catalysis of a promiscuous alanine racemase from Pseudomonas putida (KT2440) was coupled with that of PAM to increase the production of enantiopure (R)-β-arylalanines from racemic α-arylalanine substrates. The inclusion of a biocatalytic racemization along with the PAM-catalyzed reactionmoderately increased the overall reaction yield of enantiopure β-arylalanines between 4% and 19% (depending on the arylalanine), which corresponded to as much as a 63% increase compared to the turnover with the aminomutase reaction alone. The use of these biocatalysts, in tandem, could potentially find application in the production of chiral β-arylalanine building blocks, particularly, as refinements to the process are made that increase reaction flux, such as by selectively removing the desired (R)-β-arylalanine product from the reaction mixture. 2009 American Chemical Society.

Preparation of (R)-Phenylalanine Analogues by Enantioselective Destruction Using L-Amino Acid Oxidase

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