Ethyl 2-(diphenoxyphosphoryl)acetate

Base Information

• Chemical Name: Ethyl 2-(diphenoxyphosphoryl)acetate
• CAS No.: 16139-79-0
• Molecular Formula: C16H17 O5 P
• Molecular Weight: 320.282
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40453612
• Nikkaji Number: J840.188H
• Wikidata: Q82274794
• Mol file: 16139-79-0.mol

Synonyms:16139-79-0;Ethyl 2-(diphenoxyphosphoryl)acetate;Diphenylphosphonoacetic Acid Ethyl Ester;Ethyl Diphenylphosphonoacetate;Ethyl diphenylphosphono acetate;Ethyl 2-diphenoxyphosphorylacetate;C16H17O5P;Acetic acid, (diphenoxyphosphinyl)-, ethyl ester;Acetic acid, 2-(diphenoxyphosphinyl)-, ethyl ester;SCHEMBL1450572;ethyl(diphenoxyphosphoryl)acetate;DTXSID40453612;ethyl (diphenoxyphosphoryl)acetate;Ethyl (diphenoxyphosphinyl)acetate;UQMFCYBSUVRGNU-UHFFFAOYSA-N;MFCD01321165;AKOS016008526;AS-68437;D2547;A883107;4-METHOXY-2-NAPHTHYLAMINEP-TOLUENESULFONATESALT

Chemical Property of Ethyl 2-(diphenoxyphosphoryl)acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 81-82 °C
• Refractive Index: 1.544
• Boiling Point: 220 °C / 3mmHg
• Flash Point: 223.397°C
• PSA: 71.64000
• Density: 1.22
• LogP: 3.90060
• Storage Temp.: 0-10°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 320.08136064
• Heavy Atom Count: 22
• Complexity: 362

Purity/Quality:

98% ^*data from raw suppliers

DiphenylphosphonoaceticAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CP(=O)(OC1=CC=CC=C1)OC2=CC=CC=C2

Technology Process of Ethyl 2-(diphenoxyphosphoryl)acetate

There total 10 articles about Ethyl 2-(diphenoxyphosphoryl)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: 97.0%

ethyl 2-(dichlorophosphinyl)acetate (36957-54-7) + sodium phenoxide (139-02-6) → ethyl diphenylphosphonoacetate (16139-79-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1055/a-1628-7586

Reference yield: 89.0%

diphenyl methylphosphonate (7526-26-3) + chloroformic acid ethyl ester (541-41-3) → ethyl diphenylphosphonoacetate (16139-79-0)

Guidance literature:

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jo9907181

Reference yield: 86.0%

diphenyl hydrogen phosphite (4712-55-4) + ethyl bromoacetate (105-36-2) → ethyl diphenylphosphonoacetate (16139-79-0)

Guidance literature:

diphenyl hydrogen phosphite; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

ethyl bromoacetate; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1055/s-2004-831166

upstream raw materials:

ethyl 2-(dichlorophosphinyl)acetate

phenol

diphenyl methylphosphonate

chloroformic acid ethyl ester

Downstream raw materials:

ethyl (Z)-4-benzyloxypent-2-enoate

ethyl (E)-4-benzyloxypent-2-enoate

Ethyl (4S,2Z)-5-methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate

Ethyl (4S,2Z)-4-[(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]-5-methylhex-2-enoate

Refernces

• 1、 Ando, Kaori. "Practical synthesis of Z-unsaturated esters by using a new Horner-Emmons reagent, ethyl diphenylphosphonoacetate". . p. 4105 - 4108. Retrieved 1995.
• 2、 Janicki, Ignacy,Kie?basiński, Piotr. "A Straightforward, Purification-Free Procedure for the Synthesis of Ando and Still-Gennari Type Phosphonates". . p. 378 - 382. Retrieved 2021/10/21.
• 3、 Fan, Xiaohui,Lv, Hao,Guan, Yong-Hong,Zhu, Hong-Bo,Cui, Xiao-Meng,Guo, Kun. "Assembly of indenamine derivatives through in situ formed N-sulfonyliminium ion initiated cyclization". supporting information. p. 4119 - 4122. Retrieved 2014/04/03.