2-Amino-4-phosphonobutyric acid

Base Information

• Chemical Name: 2-Amino-4-phosphonobutyric acid
• CAS No.: 6323-99-5
• Molecular Formula: C4H10NO5P
• Molecular Weight: 183.101
• Hs Code.: 2931900090
• European Community (EC) Number: 622-387-0
• NSC Number: 354086,30079
• UNII: H8B59H10OK
• DSSTox Substance ID: DTXSID201017567
• Nikkaji Number: J327.345H
• Wikidata: Q27279766
• Pharos Ligand ID: Y2NF9U7TF5R8
• ChEMBL ID: CHEMBL285843
• Mol file: 6323-99-5.mol

Synonyms:2-amino-4-phosphonobutanoic acid;2-amino-4-phosphonobutyric acid;Abu(P);DL-2-amino-4-phosphobutanoic acid;DL-AP4;L-2-amino-4-phosphobutyric acid;L-2-amino-4-phosphonobutanoic acid;L-2-amino-4-phosphonobutyrate;L-AP4, butyric;L-APB

Chemical Property of 2-Amino-4-phosphonobutyric acid

Chemical Property:

• Melting Point: 229-231 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 491.7±55.0 °C(Predicted)
• PKA: 2.19±0.10(Predicted)
• PSA: 130.66000
• Density: 1.628±0.06 g/cm3(Predicted)
• LogP: -0.33360
• XLogP3: -5.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 183.02965942
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

DL-2-Amino-4-phosphonobutanoicacid(AP4) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CP(=O)(O)O)C(C(=O)O)N
• Description: DL-AP4 is a broad-spectrum glutamatergic antagonist. DL-AP4 (2.5 mM) inhibits electrically stimulated synaptic transmission in rabbit hippocampal slices. It also depresses depolarizations induced by NMDA , L-homocysteate, or kainate in isolated frog spinal cord when used at a concentration of 1 mM. DL-AP4 (0.2 mM) inhibits the accumulation of inositol induced by ibotenate , quisqualate, L-glutamate, and L-aspartate in rat hippocampal slices.

Technology Process of 2-Amino-4-phosphonobutyric acid

There total 4 articles about 2-Amino-4-phosphonobutyric 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: 85.0%

C19H20FN2O7P*C12H23N → 2-amino-4-phosphonobutyric acid (6323-99-5) + C12H23N*C4H9FNO4P

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; acetonitrile; at 0 - 20 ℃;

DOI:10.1271/bbb.63.2248

Reference yield: 65.0%

diethyl 2-bromoethylphosphonate (5324-30-1) + methyl N-(diphenylmethylene)glycinate (81167-39-7) → 2-amino-4-phosphonobutyric acid (6323-99-5)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetonitrile; for 24h; Heating;

Reference yield:

2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester (86554-31-6) → 2-Amino-4-phosphono-butyric acid (6323-99-5,20263-07-4,23052-81-5,78739-01-2) + 2-Amino-4-phosphono-butyric acid (6323-99-5,20263-07-4,23052-81-5,78739-01-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)91895-2

upstream raw materials:

diethyl 2-bromoethylphosphonate

methyl N-(diphenylmethylene)glycinate

2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester

Downstream raw materials:

3-(N-acetyl-N-hydroxyamino)propylphosphonic acid

cytidine monophosphate

CMP-5'-3-aminopropylphosphonate

cytidine diphosphate

Refernces

• 1、 Aboujaoude, E. Elia,Collignon, N.,Savignac, P.,Bensoam, J.. "SYNTHESE D'ACIDES ω-AMINO-ω-CARBOXY-ALKYLPHOSPHONIQUES". . p. 93 - 104. Retrieved 2007/10/02.