Diethyl cinnamylphosphonate

Base Information

• Chemical Name: Diethyl cinnamylphosphonate
• CAS No.: 58922-31-9
• Molecular Formula: C₁₃H₁₉O₃P
• Molecular Weight: 254.266
• NSC Number: 125942
• Nikkaji Number: J1.134.385F,J502.412I
• Mol file: 58922-31-9.mol

Synonyms:diethyl cinnamylphosphonate;58922-31-9;Diethyl trans-cinnamylphosphonate;17316-55-1;52378-69-5;(3-Phenyl-allyl)-phosphonic acid diethyl ester;[(E)-3-diethoxyphosphorylprop-1-enyl]benzene;DIETHYL TRANS-CINNAMYLPHOSPHONATE 98;NSC125942;2-METHOXYBUTANOICACID;SCHEMBL3291420;diethyl trans-cinnamyl phosphonate;AWKOMEXJXBINBQ-DHZHZOJOSA-N;MFCD00798606;AKOS017343369;Diethyl trans-cinnamylphosphonate, 98%;NSC-125942;Phosphonous acid, styryl-, diethyl ester;(E)-Cinnamylphosphonic acid diethyl ester;Diethyl trans-3-Phenyl-2-propenephosphonate;(3-Phenylallyl)phosphonic acid diethyl ester;CS-0361272;[(E)-3-diethoxyphosphoryl-prop-1-enyl]-benzene;(3-PHENYL-ALLYL)-PHOSPHONICACIDDIETHYLESTER;Phosphonous acid, (2-phenylethenyl)-, diethyl ester

Chemical Property of Diethyl cinnamylphosphonate

Chemical Property:

• Vapor Pressure: 2.74E-05mmHg at 25°C
• Boiling Point: 368.2°C at 760 mmHg
• Flash Point: 190.1°C
• PSA: 45.34000
• Density: 1.089g/cm³
• LogP: 3.96590
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 254.10718146
• Heavy Atom Count: 17
• Complexity: 260

Purity/Quality:

99% ^*data from raw suppliers

(3-PHENYL-ALLYL)-PHOSPHONIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl cinnamylphosphonate

There total 12 articles about Diethyl cinnamylphosphonate 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: 95.0%

3-bromo-1-phenyl-1-propenyl bromide (4392-24-9) + triethyl phosphite (122-52-1) → diethyl cinnamylphosphonate (52378-69-5,58922-31-9,149298-72-6)

Guidance literature:

DOI:10.1016/j.freeradbiomed.2011.02.028

Reference yield: 94.0%

3-Phenylpropenol (104-54-1) + phosphonic acid diethyl ester (762-04-9) → diethyl cinnamylphosphonate (52378-69-5,58922-31-9,149298-72-6)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tert-Amyl alcohol; for 24h; Reflux; Inert atmosphere; Dean-Stark;

DOI:10.3390/molecules21101295

Reference yield: 90.0%

cinnamyl chloride (2687-12-9) + triethyl phosphite (122-52-1) → diethyl cinnamylphosphonate (52378-69-5,58922-31-9,149298-72-6)

Guidance literature:

at 180 ℃; for 8h;

upstream raw materials:

3-Phenylpropenol

triethyl phosphite

benzaldehyde

Cinnamic acid

Downstream raw materials:

2-((1E,3E)-4-Phenyl-buta-1,3-dienyl)-cyclohex-1-enecarbaldehyde

7a-((1E,3E)-4-Phenyl-buta-1,3-dienyl)-5,6,7,7a-tetrahydro-4H-indole-2-carboxylic acid methyl ester

diethyl 3-phenylpropyl-1-phosphonate

Refernces

• 1、 -. "COMPOUND AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR". Paragraph 0136; 0137. . Retrieved 2018/08/30.
• 2、 Kurandina, Daria,Parasram, Marvin,Gevorgyan, Vladimir. "Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes". supporting information. p. 14212 - 14216. Retrieved 2017/10/13.