alpha-Methyl-DL-phenylalanine

Base Information

• Chemical Name: alpha-Methyl-DL-phenylalanine
• CAS No.: 1132-26-9
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 29224999
• NSC Number: 11202
• UNII: 67265D2JSG
• DSSTox Substance ID: DTXSID601312866
• Nikkaji Number: J347.995A
• Wikidata: Q27074405
• ChEMBL ID: CHEMBL1222268
• Mol file: 1132-26-9.mol

Synonyms:alpha-methylphenylalanine;alpha-methylphenylalanine, (D-Phe)-isomer;alpha-methylphenylalanine, (DL-Phe)-isomer;alpha-methylphenylalanine, (L-Phe)-isomer;alpha-methylphenylalanine, hydrochloride, (D-Phe)-isomer;alpha-methylphenylalanine, hydrochloride, (DL-Phe)-isomer;alpha-methylphenylalanine, hydrochloride, (L-Phe)-isomer

Chemical Property of alpha-Methyl-DL-phenylalanine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.000345mmHg at 25°C
• Melting Point: 293-294 °C (dec.)(lit.)
• Refractive Index: 1.561
• Boiling Point: 312.8 °C at 760 mmHg
• PKA: 2.25±0.10(Predicted)
• Flash Point: 143 °C
• PSA: 63.32000
• Density: 1.166 g/cm³
• LogP: 1.73140
• Storage Temp.: Store at RT.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-Methyl-DL-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC1=CC=CC=C1)(C(=O)O)N

Technology Process of alpha-Methyl-DL-phenylalanine

There total 25 articles about alpha-Methyl-DL-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

benzyl bromide (100-39-0) + C16H13N3O3(2-)*Ni(2+) → 2-methyl-3-phenylalanine (1132-26-9)

Guidance literature:

With potassium hydroxide; C-9; In dichloromethane; at 20 ℃;

DOI:10.1007/BF00959641

Reference yield: 94.0%

benzyl bromide (100-39-0) + isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate (126402-81-1) → 2-methyl-3-phenylalanine (1132-26-9)

Guidance literature:

benzyl bromide; isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate; With cesium hydroxide; (R,R)-TADDOL; In toluene; at 15 - 20 ℃; for 12h;

With hydrogenchloride; In water; toluene; Heating;

DOI:10.1007/BF02494637

Reference yield: 89.0%

(+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine (86778-91-8) → 2-methyl-3-phenylalanine (1132-26-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 2h; Ambient temperature;

upstream raw materials:

4-benzyl-2-phenyl-2-oxazolin-5-one

methyl iodide

benzyl bromide

ethyl 2-(diphenylmethyleneamino)propanoate

Downstream raw materials:

DL-α-methylphenylalanine methyl ester hydrochloride

α-Methyl-N-phthaloylphenylalanin

2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-3-phenyl-propionic acid

(+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine

Refernces

• 1、 Hu, Ai-Guo,Zhang, Ling-Yun,Wang, Shan-Wei,Wang, Ji-Tao. "Application of metal reagent to the asymmetric synthesis of α-αamino acids". . p. 2143 - 2147. Retrieved 2002.
• 2、 Drabina, Pavel,Karel, Sergej,Panov, Illia,Sedlak, Milos. "Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl) imidazolidine-4-one ligands". . p. 334 - 339. Retrieved 2013/04/23.
• 3、 -. "Lyase Enzymes, Nucleic Acids Encoding Them and Methods for Making and Using Them". . . Retrieved 2011/02/25.