Ethyl 2-(diethoxyphosphoryl)pent-4-ynoate

Base Information

• Chemical Name: Ethyl 2-(diethoxyphosphoryl)pent-4-ynoate
• CAS No.: 26199-74-6
• Molecular Formula: C11H19 O5 P
• Molecular Weight: 262.2393
• European Community (EC) Number: 631-084-2
• DSSTox Substance ID: DTXSID70402537
• Nikkaji Number: J645.119E
• Mol file: 26199-74-6.mol

Synonyms:26199-74-6;Ethyl 2-(diethoxyphosphoryl)pent-4-ynoate;2-Phosphono-4-pentynoic Acid Triethyl Ester;ethyl 2-diethoxyphosphorylpent-4-ynoate;TRIETHYL ALPHA-PROPARGYLPHOSPHONOACETATE;SCHEMBL15162611;DTXSID70402537;Ethyl2-(diethoxyphosphoryl)pent-4-ynoate;J-016322;4-Pentynoic acid,2-(diethoxyphosphinyl)-,ethyl ester

Chemical Property of Ethyl 2-(diethoxyphosphoryl)pent-4-ynoate

Chemical Property:

• Vapor Pressure: 0.00181mmHg at 25°C
• Boiling Point: 292.6°Cat760mmHg
• Flash Point: 179.1°C
• PSA: 71.64000
• Density: 1.117g/cm³
• LogP: 2.20750
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 262.09701070
• Heavy Atom Count: 17
• Complexity: 320

Purity/Quality:

98%min ^*data from raw suppliers

2-Phosphono-4-pentynoic Acid Triethyl Ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC#C)P(=O)(OCC)OCC
• Uses: 2-Phosphono-4-pentynoic Acid Triethyl Ester, can be used as an intermediate for the synthesis of pharmaceutical products including inhibitors and anticancer compounds. It is used in the synthesis of noncompetitive α-2,3-sialyltransferase inhibitor.

Technology Process of Ethyl 2-(diethoxyphosphoryl)pent-4-ynoate

There total 3 articles about Ethyl 2-(diethoxyphosphoryl)pent-4-ynoate 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: 74.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + C3H3Na (104761-12-8) → (1-Ethoxycarbonyl-3-butinyl)phosphonsaeure-diethylester (26199-74-6)

Guidance literature:

In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; at -15 - 20 ℃;

DOI:10.1055/s-0029-1216982

Reference yield: 71.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + propargyl bromide (106-96-7) → (1-Ethoxycarbonyl-3-butinyl)phosphonsaeure-diethylester (26199-74-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) room temp., 6 h, 2.) reflux, 3 h;

DOI:10.1016/S0040-4039(01)81756-1

Reference yield: 58.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + propargyl bromide (106-96-7) → ethyl 2-(diethoxyphosphoryl)-2-(2-propynyl)pent-4-ynoate (110481-63-5) + (1-Ethoxycarbonyl-3-butinyl)phosphonsaeure-diethylester (26199-74-6)

Guidance literature:

With potassium carbonate; sodium iodide; at 60 ℃; for 120h; Yields of byproduct given;

DOI:10.1055/s-1986-31824

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

propargyl bromide

C₃H₃Na

Downstream raw materials:

ethyl α-propargyl acrylate

4-(Diethoxy-phosphoryl)-2-methyl-5-oxo-1-(3-phenyl-ureido)-4-prop-2-ynyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester