Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate

Base Information

• Chemical Name: Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate
• CAS No.: 23755-73-9
• Molecular Formula: C8H16BrO5P
• Molecular Weight: 303.09
• European Community (EC) Number: 807-313-9
• DSSTox Substance ID: DTXSID90446594
• Nikkaji Number: J1.377.088C
• Mol file: 23755-73-9.mol

Synonyms:23755-73-9;triethyl phosphonobromoacetate;Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate;ethyl 2-bromo-2-diethoxyphosphorylacetate;ethyl 2-bromo-2-(diethyl phosphono)acetate;McKenna's reagent;Ethyl 2-bromo-2-diethoxyphosphoryl-acetate;ethyl 2-bromanyl-2-diethoxyphosphoryl-ethanoate;Acetic acid, bromo(diethoxyphosphinyl)-, ethyl ester;SCHEMBL7470858;DTXSID90446594;BBL102501;MFCD00233589;STL556304;ethyl bromo(diethoxyphosphoryl)acetate;AKOS015900858;AS-7009;Ethyl2-bromo-2-(diethoxyphosphoryl)acetate;CS-0336287;FT-0652883;EN300-7510018;A816885;2-bromo-2-diethoxyphosphorylacetic acid ethyl ester

Chemical Property of Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate

Chemical Property:

• Boiling Point: 128-131 °C(Press: 1 Torr)
• Density: 1.3742 g/cm3
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 301.99187
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate 95+% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(P(=O)(OCC)OCC)Br

Technology Process of Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate

There total 3 articles about Ethyl 2-bromo-2-(diethoxyphosphoryl)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: 98.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → triethyl bromophosphonoacetate (23755-73-9)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In 1,2-dimethoxyethane; at 20 ℃; for 1h;

With bromine; In 1,2-dimethoxyethane; at 0 - 20 ℃; for 2.25h;

DOI:10.1055/s-2004-831166

Reference yield: 85.0%

triethyl 2,2-dibromophosphonoacetate (28845-75-2) → triethyl bromophosphonoacetate (23755-73-9)

Guidance literature:

With tin(ll) chloride; In ethanol; water; for 0.0833333h; Ambient temperature;

DOI:10.1021/jo00376a092

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → triethyl 2,2-dibromophosphonoacetate (28845-75-2) + triethyl bromophosphonoacetate (23755-73-9)

Guidance literature:

With bromine; sodium hydroxide; Inert atmosphere;

DOI:10.1002/ejoc.201301207

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

triethyl 2,2-dibromophosphonoacetate

Refernces

• 1、 McKenna, Charles E.,Khawli, Leslie A.. "Synthesis of Halogenated Phosphonoacetate Esters". . p. 5467 - 5471. Retrieved 1986.
• 2、 Faisca Phillips, Ana Maria,Barros, Maria Teresa. "Enantioselective organocatalytic synthesis of α- cyclopropylphosphonates through a domino michael addition/intramolecular alkylation reaction". . p. 152 - 163. Retrieved 2014.
• 3、 Zhang, Xing-Gui,Li, Xin,Zhang, Chi,Feng, Chao. "Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination". supporting information. p. 9611 - 9615. Retrieved 2021/12/17.