DIBENZYLPHOSPHONOACETIC ACID

Base Information

• Chemical Name: DIBENZYLPHOSPHONOACETIC ACID
• CAS No.: 53243-58-6
• Molecular Formula: C16H16O5P-
• Molecular Weight: 320.282
• Hs Code.: 2931900090
• Mol file: 53243-58-6.mol

Synonyms:diazomethyl-P,P-diphenyl phosphine oxide;diazomethyl-diphenyl-phosphane oxide;diphenylphosphorylazide;

Chemical Property of DIBENZYLPHOSPHONOACETIC ACID

Chemical Property:

• Vapor Pressure: 2.16E-11mmHg at 25°C
• Melting Point: 46-54°C
• Boiling Point: 514°Cat760mmHg
• Flash Point: 264.7°C
• PSA: 82.64000
• Density: g/cm³
• LogP: 3.69770
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

Dibenzylphosphonoacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DIBENZYLPHOSPHONOACETIC ACID

There total 5 articles about DIBENZYLPHOSPHONOACETIC 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: 82.0%

ethyl dibenzylphosphonoacetate → α-dibenzylphosphonoacetic acid (53243-58-6)

Guidance literature:

ethyl dibenzylphosphonoacetate; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2011.12.077

Reference yield: 63.0%

carbon dioxide (124-38-9,18923-20-1) + dibenzyl methylphosphonate (19236-58-9) → α-dibenzylphosphonoacetic acid (53243-58-6)

Guidance literature:

dibenzyl methylphosphonate; With n-butyllithium; at -78 ℃;

carbon dioxide; at -78 ℃;

DOI:10.1021/jm9001764

Reference yield:

Dibenzyl phosphite (17176-77-1) → α-dibenzylphosphonoacetic acid (53243-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / toluene / 1 h / 20 °C

1.2: toluene / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -70 °C

2.2: 60 percent / hexane; tetrahydrofuran; diethyl ether / 2 h / -70 - 20 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; toluene;

DOI:10.1016/j.ejmech.2004.01.006

upstream raw materials:

carbon dioxide

dibenzyl methylphosphonate

Dibenzyl phosphite

dibenzyl hydrogen phosphite

Downstream raw materials:

(E)-3-phenylacrylic acid

(dibenzyloxyphosphoryl)acetic acid benzyl ester

(benzyloxyhydroxyphosphoryl)acetic acid benzyl ester

Refernces

• 1、 Johnson, Brad,Steadman, Rachel,Patefield, Krista D.,Bunker, Jeffrey J.,Atkin, Audrey L.,Dussault, Patrick. "N5-Phosphonoacetyl-l-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae". supporting information; experimental part. p. 2351 - 2353. Retrieved 2011/06/11.
• 2、 Grison, Claude,Coutrot, Philippe,Comoy, Corinne,Balas, Laurence,Joliez, Stephane,Lavecchia, Guido,Oliger, Patrick,Penverne, Bernadette,Serre, Valerie,Herve, Guy. "Design, synthesis and activity of bisubstrate, transition-state analogues and competitive inhibitors of aspartate transcarbamylase". . p. 333 - 344. Retrieved 2007/10/03.