Aminoethylphosphinic acid

Base Information

• Chemical Name: Aminoethylphosphinic acid
• CAS No.: 71937-28-5
• Molecular Formula: C2H8 N O2 P
• Molecular Weight: 109.065
• European Community (EC) Number: 426-930-0
• UNII: G4888SY0QO
• DSSTox Substance ID: DTXSID50995871
• Wikidata: Q27278734
• ChEMBL ID: CHEMBL37702
• Mol file: 71937-28-5.mol

Synonyms:1-aminoethylphosphinate;1-aminoethylphosphinic acid;1-aminoethylphosphinic acid, (+)-isomer;1-aminoethylphosphinic acid, (+-)-isomer;1-aminoethylphosphinic acid, sodium salt, (+-)-isomer

Chemical Property of Aminoethylphosphinic acid

Chemical Property:

• PSA: 95.92000
• LogP: -0.25280
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 108.02144046
• Heavy Atom Count: 6
• Complexity: 64.6

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(N)[P+](=O)O

Technology Process of Aminoethylphosphinic acid

There total 5 articles about Aminoethylphosphinic acid 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: 49.0%

(L,D)-1-(N-phenylacetylamino)ethylphosphinic acid (145728-55-8) → (1R)-(-)-1-aminoethylphosphinic acid (71937-28-5) + (S)-1-(N-phenylacetylamino)ethylphosphinic acid

Guidance literature:

With penicillin G acylase from Escherichia coli immobilized on mesoporous cellular foams; In aq. phosphate buffer; at 25 ℃; for 1h; pH=7; stereospecific reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2016.11.007

Reference yield: 44.0%

[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid (108327-37-3) → (1R)-(-)-1-aminoethylphosphinic acid (71937-28-5) + (S)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid

Guidance literature:

With penicillin G acylase from Escherichia coli immobilized on mesoporous cellular foams; In aq. phosphate buffer; at 25 ℃; for 72h; pH=7; stereospecific reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2016.11.007

Reference yield: 41.0%

[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid (108327-37-3) → (1R)-(-)-1-aminoethylphosphinic acid (71937-28-5) + (R)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid (115115-40-7) + (S)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid

Guidance literature:

With penicillin G acylase from Escherichia coli; In aq. phosphate buffer; at 25 ℃; for 24h; pH=7; enantioselective reaction; Kinetics; Enzymatic reaction;

DOI:10.1016/j.molcatb.2016.05.011

upstream raw materials:

[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid

(L,D)-1-(N-phenylacetylamino)ethylphosphinic acid

Downstream raw materials:

(-)-1-aminoethylphosphonic acid

(R)-1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester

(1R,2R)-3-[(1-benzyloxycarbonylamino-ethyl)hydroxy-phosphinoyl]-2-(4-bromo-benzyl)propionic acid benzyl ester

(1R,2S)-3-[(1-benzyloxycarbonylamino-ethyl)hydroxy-phosphinoyl]-2-(4-bromo-benzyl)propionic acid benzyl ester

Refernces

• 1、 Zielińska, Katarzyna,Mazurkiewicz, Roman,Szymańska, Katarzyna,Jarz?bski, Andrzej,Magiera, Sylwia,Erfurt, Karol. "Penicillin G acylase-mediated kinetic resolution of racemic 1-(N-acylamino)alkylphosphonic and 1-(N-acylamino)alkylphosphinic acids and their esters". . p. 31 - 40. Retrieved 2016/07/19.