DIETHYLPHOSPHONOACETIC ACID

Base Information

• Chemical Name: DIETHYLPHOSPHONOACETIC ACID
• CAS No.: 3095-95-2
• Molecular Formula: C6H13O5P
• Molecular Weight: 196.14
• Hs Code.: 29319090
• European Community (EC) Number: 608-560-3
• Mol file: 3095-95-2.mol

Synonyms:Aceticacid, (diethoxyphosphinyl)- (9CI);Acetic acid, phosphono-, P,P-diethyl ester(7CI,8CI);(Diethoxyphosphinyl)acetic acid;(Diethylphosphono)acetic acid;Diethoxyphosphorylacetic acid;Diethyl carboxymethanephosphonate;Diethylcarboxymethylphosphonate;NSC 272281;

Chemical Property of DIETHYLPHOSPHONOACETIC ACID

Chemical Property:

• Appearance/Colour: clear colorless to yellow viscous liquid
• Vapor Pressure: 9.07E-05mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 315.9 °C at 760 mmHg
• PKA: 3.48±0.10(Predicted)
• Flash Point: 144.9 °C
• PSA: 82.64000
• Density: 1.167 g/cm³
• LogP: 1.33710
• Storage Temp.: Store at 0-5°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 195.04223548
• Heavy Atom Count: 12
• Complexity: 175

Purity/Quality:

99.5%+ ^*data from raw suppliers

Diethylphosphonoacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)[O-])OCC
• Uses: Diethylphosphonoacetic Acid is a reagent that is used for enantioselective preparation of α-phosphoryl-α,β-unsatd.-δ-aryl-δ-lactones from nonracemic β-hydroxyaldehydes and their conversion to α-methylene-δ-aryl-δ-lactones. Acts as a nucleophile for nucleophilic addition reactions for synthesis of allene epoxidesReactant for: Stereoselectivity studies of the Staudinger reactionEnantioselective formation of diols via epoxidation and hydration reactionsHorner-Wadsworth-Emmons reactionsRemote chelation controlled Ireland-Claisen rearrangementUgi-Dieckmann reactions for synthesis of tetramic acid derivatives

Technology Process of DIETHYLPHOSPHONOACETIC ACID

There total 15 articles about DIETHYLPHOSPHONOACETIC 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: 100.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → diethylphosphonoacetic acid (3095-95-2)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 20 ℃;

Reference yield: 99.0%

benzyl diethylphosphonoacetate (7396-44-3) → diethylphosphonoacetic acid (3095-95-2)

Guidance literature:

With 1% Pd/C; hydrogen; In ethyl acetate;

DOI:10.1021/ol100071d

Reference yield: 68.0%

chloroacetic acid (79-11-8) + triethyl phosphite (122-52-1) → diethylphosphonoacetic acid (3095-95-2)

Guidance literature:

In toluene; Reflux;

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

tert-butyl diethylphosphonoacetate

benzyl diethylphosphonoacetate

Diethyl methylphosphonate

Downstream raw materials:

cyclohexylideneacetic acid

benzyl diethylphosphonoacetate

2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate

diethyl N-(benzyloxycarbonyl) amidomethyl phosphonate

Refernces

• 1、 -. "Composition comprising a phenylalanine-chloroquine derivative as an active ingredient for preventing and treating malaria infection". Paragraph 0090; 0091; 0093; 0156-0158. . Retrieved 2018/07/28.
• 2、 Brandt, Damien,Dittoo, Aurlia,Bellosta, Vronique,Cossy, Janine. "Synthetic approach to wortmannilactone C". supporting information. p. 816 - 819. Retrieved 2015/03/18.