Diethyl 2-phenylvinylphosphonate

Base Information

• Chemical Name: Diethyl 2-phenylvinylphosphonate
• CAS No.: 1018-24-2
• Molecular Formula: C12H17 O3 P
• Molecular Weight: 240.239
• NSC Number: 72385
• Nikkaji Number: J623.045H,J760.757A
• Mol file: 1018-24-2.mol

Synonyms:Diethyl 2-phenylvinylphosphonate;1018-24-2;NSC72385;NSC 72385;diethyl (e)-styrylphosphonate;(E)-diethyl styrylphosphonate;SCHEMBL8661673;Diethyl ((E)-styryl)phosphonate;Styrylphosphonic acid diethyl ester;CS-BO-00166;NSC-72385;[(E)-2-diethoxyphosphorylvinyl]benzene;[(E)-2-diethoxyphosphoryl-vinyl]-benzene

Chemical Property of Diethyl 2-phenylvinylphosphonate

Chemical Property:

• Vapor Pressure: 0.000178mmHg at 25°C
• Boiling Point: 339.6°Cat760mmHg
• Flash Point: 172.9°C
• Density: 1.108g/cm³
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 240.09153140
• Heavy Atom Count: 16
• Complexity: 247

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C=CC1=CC=CC=C1)OCC
• Isomeric SMILES: CCOP(=O)(/C=C/C1=CC=CC=C1)OCC

Technology Process of Diethyl 2-phenylvinylphosphonate

There total 29 articles about Diethyl 2-phenylvinylphosphonate 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: 99.0%

iodobenzene (591-50-4) + Diethyl vinylphosphonate (682-30-4) → diethyl styrylphosphonate (1018-24-2)

Guidance literature:

With diamminedichloropalladium(II); diisopropylamine; In water; at 80 ℃; for 6h; Reagent/catalyst; Catalytic behavior; Green chemistry;

DOI:10.1039/c7ra06464k

Reference yield: 97.0%

(E/Z)-styryl 4-methylbenzensulfonate (37611-16-8) + phosphonic acid diethyl ester (762-04-9) → diethyl styrylphosphonate (1018-24-2)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 1,10-Phenanthroline; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 12h; Inert atmosphere; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.7b01561

Reference yield: 96.0%

bromostyrene (103-64-0,1340-14-3) + triethyl phosphite (122-52-1) → diethyl styrylphosphonate (1018-24-2)

Guidance literature:

With triethylamine; In water; at 100 ℃; for 10.5h; Green chemistry;

DOI:10.1039/c5ra27330g

upstream raw materials:

phenylacetylene

triethyl phosphite

E-styryl iodide

(diethoxyphosphinyl)mercury chloride

Downstream raw materials:

(3t-benzoyl-2,5t-diphenyl-isoxazolidin-4r-yl)-phosphonic acid diethyl ester

styrylphosphonic acid

[1-(Methoxy-phenyl-methyl)-3-phenyl-2-phenylamino-propyl]-phosphonic acid diethyl ester

[1-(Hydroxy-phenyl-methyl)-3-phenyl-2-phenylamino-propyl]-phosphonic acid diethyl ester

Refernces

• 1、 Sobhani, Sara,Hosseini Moghadam, Hadis,Skibsted, J?rgen,Sansano, José Miguel. "A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water". . p. 1353 - 1365. Retrieved 2020.
• 2、 Hachemi, Messaoud,Puciova-Sebova, Monika,Toma, Stefan,Villemin, Didier. "Dry reaction of diethyl cyanomethylphosphonate and tetraethyl methylenediphosphonate with benzaldehyde on solid bases". . p. 131 - 136. Retrieved 1996.
• 3、 Iranpoor, Nasser,Firouzabadi, Habib,Rajabi Moghadam, Khashayar,Motavalli, Somayeh. "First reusable ligand-free palladium catalyzed C-P bond formation of aryl halides with trialkylphosphites in neat water". . p. 55732 - 55737. Retrieved 2014.
• 4、 Orsini, Fulvia. "Reformatsky-type co-mediated synthesis of β-hydroxyphosphonates". . p. 1425 - 1428. Retrieved 1998.