Diethyl 3-butenylphosphonate

Base Information

• Chemical Name: Diethyl 3-butenylphosphonate
• CAS No.: 15916-48-0
• Molecular Formula: C8H17 O3 P
• Molecular Weight: 192.195
• Hs Code.: 2931900090
• European Community (EC) Number: 627-868-9
• DSSTox Substance ID: DTXSID70451247
• Nikkaji Number: J694.624K
• Wikidata: Q82271178
• Mol file: 15916-48-0.mol

Synonyms:Diethyl 3-butenylphosphonate;15916-48-0;4-diethoxyphosphorylbut-1-ene;diethyl but-3-en-1-ylphosphonate;DIETHYL-3-BUTENYLPHOSPHONATE 95;P-3-Buten-1-yl-phosphonic acid diethyl ester;diethyl but-3-enylphosphonate;SCHEMBL212199;diethylbut-3-en-1-ylphosphonate;DTXSID70451247;NUDGAPYPOAQVLP-UHFFFAOYSA-N;Diethyl 3-butenylphosphonate, 95%;diethyl (but-3-en-1-yl)phosphonate;3-Butenylphosphonic acid diethyl ester;AKOS015916207;J-009571

Chemical Property of Diethyl 3-butenylphosphonate

Chemical Property:

• Vapor Pressure: 0.053mmHg at 25°C
• Refractive Index: 1.425
• Boiling Point: 55 °C0.55 mm Hg(lit.)
• Flash Point: 222 °F
• PSA: 45.34000
• Density: 1.005 g/mL at 25 °C(lit.)
• LogP: 2.82860
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 192.09153140
• Heavy Atom Count: 12
• Complexity: 158

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl 3-butenylphosphonate 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CCC=C)OCC
• Uses: Reactant for synthesis of:Bicyclo[3.3.1]alkenone framework compounds by gold-catalyzed Diels-Alder reactionsAntiviral C-5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substratesAntimalarials via halogenation of di-Et butenylphosphonateBisphosphonate enynesReactant for:Remote supramolecular control of catalyst selectivity in hydroformlyation of alkenesIntermolecular metal-catalyzed carbenoid cyclopropanationsChemoenzymatic synthesis of phosphic derivatives of carbohydrates

Technology Process of Diethyl 3-butenylphosphonate

There total 10 articles about Diethyl 3-butenylphosphonate 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: 88.0%

diethyl iodomethanephosphonate (10419-77-9) + allyltributylstanane (24850-33-7) → diethyl but-3-en-1-ylphosphonate (15916-48-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In acetonitrile; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol4005257

Reference yield: 85.0%

1-bromo-4-butene (5162-44-7) + triethyl phosphite (122-52-1) → diethyl but-3-en-1-ylphosphonate (15916-48-0)

Guidance literature:

at 240 ℃; for 3h; under 15001.5 Torr;

DOI:10.1002/anie.201806343

Reference yield: 78.0%

1-bromo-4-butene (5162-44-7) + phosphonic acid diethyl ester (762-04-9) → diethyl but-3-en-1-ylphosphonate (15916-48-0)

Guidance literature:

phosphonic acid diethyl ester; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

1-bromo-4-butene; In tetrahydrofuran;

DOI:10.1016/j.bmc.2019.01.016

upstream raw materials:

Diethyl methylphosphonate

allyl bromide

diethyl-1-magnesium chloride methanephosphonate

1-bromo-4-butene

Downstream raw materials:

diethyl (3-oxopropyl)phosphonate

{4-[5-(3-Benzoyl-2-methyl-isothioureido)-4-carbamoyl-[1,2,3]triazol-1-ylmethoxy]-butyl}-phosphonic acid diethyl ester

Refernces

• 1、 Kabak et al.. "". . p. 1074. Retrieved 1972.
• 2、 Courtens, Charlotte,Risseeuw, Martijn,Caljon, Guy,Cos, Paul,Martin, Anandi,Van Calenbergh, Serge. "Phosphonodiamidate prodrugs of N-alkoxy analogs of a fosmidomycin surrogate as antimalarial and antitubercular agents". . p. 1051 - 1053. Retrieved 2019.
• 3、 Rohde, Laurence N.,Wild, Thérèse H.,Diver, Steven T.. "Ene-Yne Metathesis of Allylphosphonates and Allylphosphates: Synthesis of Phosphorus-Containing 1,3-Dienes". . p. 1371 - 1384. Retrieved 2021/02/05.