(2R)-azaniumyl(phenyl)acetate

Base Information

• Chemical Name: (2R)-azaniumyl(phenyl)acetate
• CAS No.: 875-74-1
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: 2942.00
• Mol file: 875-74-1.mol

Synonyms:(D)-phenylglycine zwitterion;(R)-phenylglycine zwitterion;(2R)-ammonio(phenyl)acetate;(2R)-azaniumyl(phenyl)acetate;D-alpha-phenylglycine zwitterion;CHEBI:77399;(R)-2-amino-2-phenylacetic acid zwitterion

Chemical Property of (2R)-azaniumyl(phenyl)acetate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00107mmHg at 25°C
• Melting Point: 302 °C (dec.)(lit.)
• Refractive Index: -158 ° (C=1, 1mol/L HCl)
• Boiling Point: 288.7 °C at 760 mmHg
• PKA: 1.94±0.10(Predicted)
• Flash Point: 128.4 °C
• PSA: 63.32000
• Density: 1.246 g/cm³
• LogP: 1.47130
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Sparingly), Water (Slightly, Heated)
• Water Solubility.: 0.3g/100mL
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

98% ^*data from raw suppliers

D-(-)-2-Phenylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38-22-20
• Safety Statements: 22-24/25-45-36/37/39-26-44-28-7-4

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C(=O)[O-])[NH3+]
• Description: L-phenylglycine (Cephalexin EP Impurity A) is a derivative of glycine, a non-essential amino acid for human development. Glycine is an inhibitory neurotransmitter in the spinal cord and an allosteric modulator of NMDA receptors.
• Uses: D-(-)-2-Phenylglycine is the derivative of glycine (G615990), a non-essential amino acid for human development. Glycine is an inhibitory neurotransmitter in spinal cord, allosteric regulator of NMDA r eceptors. D-(-)-2-Phenylglycine (Cefalexin EP Impurity A) is the derivative of glycine (G615990), a non-essential amino acid for human development. Glycine is an inhibitory neurotransmitter in spinal cord, allosteric regulator of NMDA receptors.

Technology Process of (2R)-azaniumyl(phenyl)acetate

There total 121 articles about (2R)-azaniumyl(phenyl)acetate 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:

phenylglycin (2835-06-5) → (R)-phenylglycine (875-74-1) + Benzoylformic acid (611-73-4) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

Reference yield:

phenylglycine methyl ester (24461-61-8,26682-99-5,37760-98-8,6591-61-3) → (R)-Phenylglycine methyl ester (24461-61-8) + (S)-2-phenylglycine (2935-35-5) + (R)-phenylglycine (875-74-1) + (S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8)

Guidance literature:

With Bacillus licheniformis; sodium hydrogencarbonate; 1-ethyl-3-methylimidazolium acetate; In water; water-d2; at 30 ℃; for 24h;

DOI:10.1016/j.tetasy.2006.09.009

Reference yield:

2-amino-2-phenyl malonic acid (51619-79-5) → (R)-phenylglycine (875-74-1) + phenylglycin (2835-06-5)

Guidance literature:

With recombinant Bordetella bronchiseptica arylmalonate decarboxylase from E_. coli BL₂₁ (DE₃); optical yield given as %ee; Enzymatic reaction;

DOI:10.1002/anie.200904112

upstream raw materials:

Chloro-phenyl-acetic acid

(R)-phenylglycine amide

N-[(2S)-(benzoylamino)(phenyl)]ethanoic acid

(R)-2-bromo-2-phenylacetic acid

Downstream raw materials:

(R)-Phenylglycine methyl ester

(R)-amino-phenyl-acetic acid ethyl ester

(R)-2-amino-2-cyclohexyl acetic acid

(4-nitro-benzoyl)-(d(-)-α-amino-phenylacetic acid )

Refernces

• 1、 Timmermans,Motiuk. "-". . p. 399,408, 410. Retrieved 1932.
• 2、 Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong. "Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography". supporting information. p. 390 - 398. Retrieved 2021/01/13.
• 3、 Lee, Jae Hwan,Ryoo, Jae Jeong. "Ultrasound-Controlled Chiral Separation of Four Amino Acids and 2,2,2-Trifluoro-1-(9-anthryl)ethanol". . p. 146 - 149. Retrieved 2019/02/07.