Diethylphenylphosphine

Base Information

• Chemical Name: Diethylphenylphosphine
• CAS No.: 1605-53-4
• Molecular Formula: C10H15P
• Molecular Weight: 166.203
• Hs Code.: 29319090
• European Community (EC) Number: 216-516-6
• NSC Number: 158475
• DSSTox Substance ID: DTXSID40166891
• Nikkaji Number: J80.256E
• Wikidata: Q72462093
• Mol file: 1605-53-4.mol

Synonyms:diethylphenylphosphine

Chemical Property of Diethylphenylphosphine

Chemical Property:

• Appearance/Colour: irritable\smell \colorless liquid
• Vapor Pressure: 0.0839mmHg at 25°C
• Melting Point: 45 °C
• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 233.7 °C at 760 mmHg
• Flash Point: 97.5 °C
• PSA: 13.59000
• Density: 0.954 g/mL at 25 °C(lit.)
• LogP: 2.83360
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 166.091137476
• Heavy Atom Count: 11
• Complexity: 91

Purity/Quality:

98% ^*data from raw suppliers

Diethylphenylphosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 17-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCP(CC)C1=CC=CC=C1
• Uses: Diethylphenylphosphine is used as a catalyst for selective cross-dimerization, carboxyl migration reactions, selective hydrogenation, asymmetric induction by chiral diphosphines in ring contraction.

Technology Process of Diethylphenylphosphine

There total 20 articles about Diethylphenylphosphine 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: 65.0%

ethylmagnesium bromide (925-90-6) + Dichlorophenylphosphine (644-97-3) → diethyl-phenyl-phosphine (1605-53-4)

Guidance literature:

In diethyl ether; at 0 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201803477

Reference yield:

diethylphenylphosphine oxide (24323-92-0) → diethyl-phenyl-phosphine (1605-53-4)

Guidance literature:

With chloro-trimethyl-silane; magnesium; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2014.12.132

Reference yield:

iodobenzene (591-50-4) + diethylphosphine oxide (7215-33-0) → diethyl-phenyl-phosphine (1605-53-4)

Guidance literature:

diethylphosphine oxide; With copper(II) trifluoromethanesulfonate; 1,1,3,3-Tetramethyldisiloxane; In toluene; at 100 ℃; for 10h; Inert atmosphere;

iodobenzene; With caesium carbonate; N,N`-dimethylethylenediamine; In toluene; at 20 - 110 ℃; Inert atmosphere;

DOI:10.1021/ja301764m

upstream raw materials:

(diethyl-phenyl-phosphoranylidene)-fluoren-9-ylidene-hydrazine

ethylmagnesium bromide

Dichlorophenylphosphine

ethyl bromide

Downstream raw materials:

triethylphenylphosphonium iodide

N-(diethyl-phenyl-phosphoranyliden)-aniline

diphenyl(methyl)phosphine

ethyl-diphenyl-phosphane

Refernces

• 1、 Bianco,Doronzo. "-". . p. 169,172. Retrieved 1978.
• 2、 Stevens, Michael A.,Hashim, Fairuz H.,Gwee, Eunice S. H.,Izgorodina, Ekaterina I.,Mulvey, Robert E.,Blair, Victoria L.. "Contrasting Synergistic Heterobimetallic (Na–Mg) and Homometallic (Na or Mg) Bases in Metallation Reactions of Dialkylphenylphosphines and Dialkylanilines: Lateral versus Ring Selectivities". . p. 15669 - 15677. Retrieved 2018/09/27.
• 3、 O'Brien, Christopher J.,Nixon, Zachary S.,Holohan, Andrew J.,Kunkel, Stephen R.,Tellez, Jennifer L.,Doonan, Bryan J.,Coyle, Emma E.,Lavigne, Florie,Kang, Lauren J.,Przeworski, Katherine C.. "Part I: The development of the catalytic wittig reaction". supporting information. p. 15281 - 15289. Retrieved 2013/11/06.