CID 6951090

Base Information

• Chemical Name: CID 6951090
• CAS No.: 103616-89-3
• Molecular Formula: C9H10ClNO2
• Molecular Weight: 199.637
• Hs Code.: 29224999
• Mol file: 103616-89-3.mol

Synonyms:

Chemical Property of CID 6951090

Chemical Property:

• Melting Point: 233-235 °C
• Boiling Point: 339.5 °C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 159.1 °C
• PSA: 63.32000
• Density: 1.336 g/cm³
• LogP: 1.99470
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Water (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 199.0400063
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

2-Chloro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC(C(=O)[O-])[NH3+])Cl
• Isomeric SMILES: C1=CC=C(C(=C1)C[C@@H](C(=O)[O-])[NH3+])Cl
• Uses: The largest gain in affinity of all tested unnatural amino acids was observed for 2-chloro-L-phenylalanine.

Technology Process of CID 6951090

There total 14 articles about CID 6951090 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: 91.0%

o-chlorocinnamic acid (3752-25-8,939-58-2) → (2S)-2-amino-3-(2-chlorophenyl)propanoic acid (103616-89-3,80126-50-7)

Guidance literature:

With sulfuric acid; ammonia; E_.coli cells containing phenylalanine ammonia lyase (PAL) gene of R_.glutinis; In water; at 30 ℃; for 8.5h; pH=11;

Reference yield: 48.0%

rac-2-chlorophenylalanine (14091-11-3,80126-50-7) → (2S)-2-amino-3-(2-chlorophenyl)propanoic acid (103616-89-3,80126-50-7)

Guidance literature:

With sodium hydroxide; oxygen; at 30 ℃; for 43h; pH=7.3; optical yield given as %ee; enantioselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.bmcl.2008.12.100

Reference yield: 37.0%

trans-2-chlorocinnamic acid (704-96-1,939-58-2) → (2S)-2-amino-3-(2-chlorophenyl)propanoic acid (103616-89-3,80126-50-7)

Guidance literature:

With ammonium hydroxide; Petroselinum crispum phenylalanine ammonialyase (1U); at 37 ℃; for 24h; pH=10;

DOI:10.1002/1521-3765(20000915)6:18<3386::AID-CHEM3386>3.0.CO;2-5

upstream raw materials:

(S)-N-acetyl-o-chlorophenylalanine

trans-2-chlorocinnamic acid

rac-2-chlorophenylalanine

N-acetyl-3-(2-chlorophenyl)-2-ethoxycarbonyl alanine ethyl ester

Downstream raw materials:

N^α-[(tert-butoxy)carbonyl]-2-(chloro)-L-phenylalanine

(R)-2'-chlorophenylalanine

Refernces

• 1、 Varga, Andrea,Bánóczi, Gergely,Nagy, Botond,Bencze, László Csaba,To?a, Monica Ioana,Gellért, ákos,Irimie, Florin Dan,Rétey, János,Poppe, László,Paizs, Csaba. "Influence of the aromatic moiety in α- And β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from: Pantoea agglomerans". . p. 56412 - 56420. Retrieved 2016.
• 2、 Weise, Nicholas J.,Parmeggiani, Fabio,Ahmed, Syed T.,Turner, Nicholas J.. "The bacterial ammonia lyase EncP: A tunable biocatalyst for the synthesis of unnatural amino acids". . p. 12977 - 12983. Retrieved 2015.
• 3、 Gloge, Andreas,Zon, Jerzy,Koevari, Agnes,Poppe, Laszlo,Retey, Janos. "Phenylalanine ammonia-lyase: The use of its broad substrate specificity for mechanistic investigations and biocatalysis - Synthesis of L-arylalanines". . p. 3386 - 3390. Retrieved 2000.
• 4、 Zhang, Zizhang. "Use of whole cell culture of Aeromonas sp. as enantioselective scavenger: A facile preparation of l-amino acid derivatives in high enantiomeric excess". . p. 1129 - 1131. Retrieved 2009.