(2S)-2-azaniumyl-2-(2-chlorophenyl)acetate

Base Information

• Chemical Name: (2S)-2-azaniumyl-2-(2-chlorophenyl)acetate
• CAS No.: 141315-50-6
• Molecular Formula: C8H8ClNO2
• Molecular Weight: 185.61
• Hs Code.: 2922499990
• Mol file: 141315-50-6.mol

Synonyms:

Chemical Property of (2S)-2-azaniumyl-2-(2-chlorophenyl)acetate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000148mmHg at 25°C
• Melting Point: 182-187 °C(lit.)
• Refractive Index: 1.603
• Boiling Point: 386.6 °C at 760 mmHg
• PKA: 1.69±0.10(Predicted)
• Flash Point: 187.6 °C
• PSA: 63.32000
• Density: 1.406 g/cm³
• LogP: 2.12470
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 185.0243562
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

L-2-Chlorophenylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(C(=O)[O-])[NH3+])Cl
• Isomeric SMILES: C1=CC=C(C(=C1)[C@@H](C(=O)[O-])[NH3+])Cl
• Uses: L-2-Chlorophenylglycine

Technology Process of (2S)-2-azaniumyl-2-(2-chlorophenyl)acetate

There total 14 articles about (2S)-2-azaniumyl-2-(2-chlorophenyl)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: 58.0%

sodium cyanide (143-33-9,25596-52-5) + 2-chloro-benzaldehyde (89-98-5) → 2-amino-(2-chlorophenyl)ethanoic acid (86169-24-6,141196-64-7,141315-50-6,88744-36-9)

Guidance literature:

sodium cyanide; 2-chloro-benzaldehyde; With ammonium bicarbonate; In methanol; water; at 65 - 70 ℃; for 5h;

With sodium hydroxide; In methanol; water; at 120 ℃; for 4h;

With sulfuric acid; In methanol; water; pH=7 - 8;

Reference yield: 46.0%

2-(2-chlorophenyl)-2-[(2-phenylacetyl)amino]ethanoic acid → (R)-2-(2-chlorophenyl)-2-[(2-phenylacetyl)amino]ethanoic acid (1098100-07-2) + (S)-2-amino-(2-chlorophenyl)ethanoic acid (141315-50-6)

Guidance literature:

2-(2-chlorophenyl)-2-[(2-phenylacetyl)amino]ethanoic acid; With hydrogenchloride; ammonium hydroxide; penicillin G amidohydrolase; In water; at 27 ℃; for 5h; pH=8.0; Enzymatic reaction;

With hydrogenchloride; In water; pH=2; Cooling with ice;

In water; pH=7.0; optical yield given as %ee;

DOI:10.1016/j.tetasy.2008.10.015

Reference yield:

5-(2-chlorophenyl)imidazolidine-2,4-dione (103029-09-0) → 2-amino-(2-chlorophenyl)ethanoic acid (86169-24-6,141196-64-7,141315-50-6,88744-36-9)

Guidance literature:

With sodium hydroxide;

DOI:10.1039/jr9620001440

upstream raw materials:

ortho-chlorophenylmalonic acid

5-(2-chlorophenyl)imidazolidine-2,4-dione

sodium cyanide

2-chloro-benzaldehyde

Downstream raw materials:

N-Boc-(S)-2-chlorophenylglycine

S(+)-chlorophenylglycine-d-camphoric sulfonic acid

[(tert-butoxycarbonyl)amino](2-chlorophenyl)acetic acid

N-(4-methoxyphenyl)-2-chlorobenzylidenimine

Refernces

• 1、 Krueger, Clinton A.,Kuntz, Kevin W.,Dzierba, Carolyn D.,Wirschun, Wolfgang G.,Gleason, John D.,Snapper, Marc L.,Hoveyda, Amir H.. "Ti-catalyzed enantioselective addition of cyanide to imines. A practical synthesis of optically pure α-amino acids". . p. 4284 - 4285. Retrieved 1999.
• 2、 Li, Jing,Pan, Jiang,Zhang, Jie,Xu, Jian-He. "Stereoselective synthesis of l-tert-leucine by a newly cloned leucine dehydrogenase from Exiguobacterium sibiricum". . p. 11 - 17. Retrieved 2014.
• 3、 -. "Preparation method for D, L-phenylglycine and analogue thereof". Paragraph 0049; 0050. . Retrieved 2017/03/17.