Triphenylphosphine

Base Information

• Chemical Name: Triphenylphosphine
• CAS No.: 603-35-0
• Deprecated CAS: 112771-47-8,630403-25-7,1198579-87-1,1198579-87-1
• Molecular Formula: C18H15P
• Molecular Weight: 262.291
• Hs Code.: HOSPHINE PRODUCT IDENTIFICATION
• European Community (EC) Number: 210-036-0
• ICSC Number: 0700
• NSC Number: 215203,10
• UN Number: 3077
• UNII: 26D26OA393
• DSSTox Substance ID: DTXSID5026251
• Nikkaji Number: J1.652G
• Wikipedia: Triphenylphosphine
• Wikidata: Q115493
• ChEMBL ID: CHEMBL1448331
• Mol file: 603-35-0.mol

Synonyms:triphenylphosphine;triphenylphosphine hydrobromide;triphenylphosphine hydrochloride

Chemical Property of Triphenylphosphine

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 5 mm Hg ( 20 °C)
• Melting Point: 79-81 °C(lit.)
• Refractive Index: 1.6358
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 181.7 °C
• PSA: 13.59000
• Density: 1.132 g/cm³
• LogP: 3.44480
• Storage Temp.: Store at RT.
• Solubility.: water: soluble0.00017 g/L at 22°C
• Water Solubility.: Insoluble
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 262.091137476
• Heavy Atom Count: 19
• Complexity: 202
• Transport DOT Label: Class 9

Purity/Quality:

98% ^*data from raw suppliers

Triphenylphosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn,N
• Statements: 22-43-53-50/53-48/20/22
• Safety Statements: 36/37-60-61-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the nervous system. This may result in impaired functions.
• description: Triphenylphosphine (TPP) is an important ligand, and is also utilized in the Wittig reaction for alkene synthesis. This reaction involves the formation of alkyliden-etriphenylphosphoranes from the action of butyllithium or other base on the quarternary halide.Triphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. TPP is a highly efficient product that serves successfully in many applications, for example:The important ligands of homogeneous catalysts used in petrochemicals and fine chemicals production, as a co-catalyst in isobutanol and n-butanol production.The basic raw material of rhodium phosphine complex catalyst, It is used to prepare Wilkinson's catalyst, RhCl(PPh3)3 useful to catalyze the hydrogenation of alkenes and tetrakis(triphenylphosphine)palladium(0) that is widely used to catalyze C-C coupling reactions in organic synthesis.In the dye industry, Triphenylphosphine is used as sensitizer, heat stabilizers, light stabilizers, antioxidants, flame retardants, antistatic agents, rubber antiozonants and analytical reagent.
• Uses: Triphenylphosphine is first sulfonated with oleum to form the trisulfonic acid.Triphenylphosphine can be used in Wittig synthesis. It is a standard ligand in homogeneous catalysis.Triphenylphosphine is used in the synthesis of an organophosphorus intermediate, trimethyl phosphite in ester exchange method. And then a series of organophosphorus pesticides such as dichlorvos, monocrotophos and phosphamidon can be further obtained.In addition, it can be used as stabilizers in the synthesis of rubber and resins, antioxidants in polyvinyl chloride, and raw material in the synthesis of alkyd resins and polyester resins. Triphenylphosphine is used in the synthesis of Chlorambucil with cytotoxicity in breast and pancreatic cancers. Also used in the preparation of α-Tocopherol analogues for monitoring antioxidant status.

Technology Process of Triphenylphosphine

There total 673 articles about Triphenylphosphine 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%

butylidenetriphenylphosphorane (3728-50-5) + Chlorodifluoromethane (75-45-6) → 1,1-difluoro-1-pentene (4980-66-9) + butyltriphenylphosphonium chloride (13371-17-0) + triphenylphosphine (603-35-0)

Guidance literature:

In various solvent(s); Product distribution; Mechanism;

DOI:10.1021/jo00155a001

Reference yield: 84.0%

pentaphenylphosphorane (2588-88-7) → benzaldehyde (100-52-7) + triphenylphosphine (603-35-0) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With formaldehyd; In toluene; at 130 - 150 ℃; for 2h; Product distribution;

Reference yield: 62.0%

chloro-trimethyl-silane (75-77-4) + Triphenylphosphine oxide (791-28-6) + benzyl alcohol (100-51-6,185532-71-2) → Hexamethyldisiloxane (107-46-0) + benzaldehyde (100-52-7) + triphenylphosphine (603-35-0)

Guidance literature:

With 2,6-dimethylpyridine; tetrabutylammonium tetrafluoroborate; In acetonitrile; at 40 ℃; Electrochemical reaction;

DOI:10.1002/anie.202100193

upstream raw materials:

triphenyl phosphite

bromobenzene

triphenyl-arsane

(triphenylphosphoranylidene-hydrazono)-malonic acid diethyl ester

Downstream raw materials:

picoline

(triphenylphosphoranylidene-hydrazono)-acetic acid ethyl ester

(triphenylphosphoranylidene-hydrazono)-malonic acid diethyl ester

dodecyltriphenylphosphonium bromide

Refernces

• 1、 Kiso et al.. "-". . p. 2779,2780. Retrieved 1967.
• 2、 Nombel, Paul,Lugan, No?l,Donnadieu, Bruno,Lavigne, Guy. "Cluster-Mediated Conversion of Diphenylacetylene into α-Phenylcinnamaldehyde. Construction of a Catalytic Hydroformylation Cycle Based on Isolated Intermediates". . p. 187 - 196. Retrieved 1999.
• 3、 George, Adrian T.,Koczon, Lenore M.,Tisdale, Robert C.,Gebreyes, Kassu,Ma, Lidun,et al.. "". . p. 545 - 552. Retrieved 1990.
• 4、 Evans, D.,Osborn, J. A.,Jardine, F. H.,Wilkinson, G.. "". . p. 1203 - 1204. Retrieved 1965.
• 5、 Osman, Fayez H.,El-Samahy, Fatma A.. "The behavior of 3,3-diphenylindan-1,2-dione towards phosphonium ylides". . p. 545 - 552. Retrieved 2007.
• 6、 Majundar, A. K.,Mukherjee, A. K.,Bhattacharya, R. G.. "". . p. 386 - 387. Retrieved 1964.
• 7、 Tanaka, Hideo,Yano, Tomotake,Kobayashi, Kazuma,Kamenoue, Syogo,Kuroboshi, Manabu,Kawakubo, Hiromu. "TMSCl-promoted electroreduction of triphenylphosphine oxide to triphenylphosphine". . p. 582 - 584. Retrieved 2011.
• 8、 Woods, T. A.,Boyd, T. E.,Biehl, E. R.,Reeves, P. C.. "". . p. 2416 - 2418. Retrieved 1975.
• 9、 Yanilkin,Gromakov,Nigmadzyanov. "Electrochemical deoxygenation of triphenylphosphine oxide". . p. 1257 - 1258. Retrieved 1996.
• 10、 Yano, Tomotake,Kuroboshi, Manabu,Tanaka, Hideo. "Electroreduction of triphenylphosphine dichloride and the efficient one-pot reductive conversion of phosphine oxide to triphenylphosphine". . p. 698 - 701. Retrieved 2010.