Diethyl (2-methylallyl)phosphonate

Base Information

• Chemical Name: Diethyl (2-methylallyl)phosphonate
• CAS No.: 51533-70-1
• Molecular Formula: C8H17O3P
• Molecular Weight: 192.195
• Hs Code.: 2931900090
• European Community (EC) Number: 624-970-5
• DSSTox Substance ID: DTXSID30451687
• Nikkaji Number: J502.407B
• Wikidata: Q82271833
• Mol file: 51533-70-1.mol

Synonyms:Diethyl (2-methylallyl)phosphonate;51533-70-1;3-diethoxyphosphoryl-2-methylprop-1-ene;diethyl (2-methylprop-2-en-1-yl)phosphonate;DIETHYL (2-METHYLALLYL)PHOSPHONATE 97;SCHEMBL246310;DTXSID30451687;AKOS024264222;2-Methylallylphosphonic acid diethyl ester;Diethyl (2-methylallyl)phosphonate, 97%

Chemical Property of Diethyl (2-methylallyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.0539mmHg at 25°C
• Refractive Index: n20/D 1.4380(lit.)
• Boiling Point: 62 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 45.34000
• Density: 1.013 g/mL at 25 °C(lit.)
• LogP: 2.82860
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 192.09153140
• Heavy Atom Count: 12
• Complexity: 179

Purity/Quality:

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

Diethyl (2-methylallyl)phosphonate 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC(=C)C)OCC
• Uses: Diethyl (2-methylallyl)phosphonate can be used as a reagent in the Horner-Wadsworth-Emmons reaction to form conjugated carbon–carbon double bonds. It can also be used as a reactant for: Enantioselective total synthesis of 10-isocyano-4-cadinene as antifouling agent. Regiospecific preparation of 4-oxo-2-alkenylphosphonates (OAP) via silylation followed by Friedel-Crafts acylation and isomerization. OAP can serve as building blocks for the construction of polyethylenic chains. The synthesis of azaphosphone as a potent analgesic/anti-inflammatory agents.

Technology Process of Diethyl (2-methylallyl)phosphonate

There total 1 articles about Diethyl (2-methylallyl)phosphonate 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: 15.0%

methallyl acetate (820-71-3) + triethyl phosphite (122-52-1) → triethyl phosphate (78-40-0) + diethyl (2-methylallyl)phosphonate (51533-70-1)

Guidance literature:

With palladium(II) acetylacetonate; In 1,4-dioxane; at 145 - 160 ℃; for 17h;

DOI:10.1080/00397919208019075

Reference yield: 88.0%

diethyl (2-methylallyl)phosphonate (51533-70-1) → Diethyl (2-oxopropyl)phosphonate (1067-71-6)

Guidance literature:

With dimethylsulfide; ozone; In dichloromethane;

DOI:10.1080/00397919808004906

Reference yield: 76.7%

diethyl (2-methylallyl)phosphonate (51533-70-1) + ethyl 5-acetyl-1-phenyl-4-((phenylimino)methyleneamino)-1H-pyrazole-3-carboxylate → ethyl 5-acetyl-4-(2-ethoxy-4-methyl-6-(phenylamino)-1H-1,2-azaphosphinine-2-oxide)-1-phenyl-1H-pyrazole-3-carboxylate

Guidance literature:

With sodium ethanolate; In ethanol; for 6h; Reflux;

DOI:10.1039/c2ra22769j

upstream raw materials:

methallyl acetate

triethyl phosphite

Downstream raw materials:

Diethyl (2-oxopropyl)phosphonate

(E)-diethyl (2-methyl-4-phenylbut-1-en-1-yl)phosphonate

(E)-2-methyl-4-phenyl-1,3-butadiene

(1E)-1-cyclohexyl-3,3-dimethyl-1,3-butadiene

Refernces