Triphenyl phosphite

Base Information

• Chemical Name: Triphenyl phosphite
• CAS No.: 101-02-0
• Molecular Formula: C18H15O3P
• Molecular Weight: 310.289
• Hs Code.: HOSPHITE PRODUCT IDENTIFICATION
• European Community (EC) Number: 202-908-4
• ICSC Number: 1124
• NSC Number: 62219,43789
• UN Number: 2811
• UNII: 9P45GRD24X
• DSSTox Substance ID: DTXSID0026252
• Nikkaji Number: J3.594G
• Wikipedia: Triphenyl_phosphite
• Wikidata: Q222290
• ChEMBL ID: CHEMBL1875503
• Mol file: 101-02-0.mol

Synonyms:triphenyl phosphite

Chemical Property of Triphenyl phosphite

Chemical Property:

• Appearance/Colour: colourless to pale yellow liquid
• Vapor Pressure: 5 mm Hg ( 205 °C)
• Melting Point: 22-24 °C
• Refractive Index: n20/D 1.59(lit.)
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 218.3 °C
• PSA: 41.28000
• Density: 1.184 g/mL at 25 °C(lit.)
• LogP: 5.45030
• Storage Temp.: -20°C
• Sensitive.: Air & Moisture Sensitive
• Solubility.: methanol: 25 mg/mL, clear
• Water Solubility.: insoluble
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 310.07588133
• Heavy Atom Count: 22
• Complexity: 247
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Triphenyl Phosphite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,Xi
• Hazard Codes: Xn,N,Xi
• Statements: 36/38-50/53
• Safety Statements: 28-60-61-28A-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphite Compounds
• Canonical SMILES: C1=CC=C(C=C1)OP(OC2=CC=CC=C2)OC3=CC=CC=C3
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the nervous system at high doses.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: (1) Triphenyl phosphite is used as chelating agents, plastics antioxidant, alkyd resin and pesticide intermediate raw material. (2) It is used for synthetic rubber and resin stabilizer, PVC antioxidant, alkyd resin and pesticide intermediate raw material. (3) Triphenyl phosphite is used as secondary antioxidants, it has effect of light stability, it is suitable for polyvinyl chloride, polypropylene, polystyrene, polyester, ABS resin, and epoxy resin. (4) It is used as chelating agent in PVC products, it can enable products to maintain transparency, and suppresse color change. It can also be used for the production of trimethyl phosphite. (5) Antioxidants, stabilizers TPPi is mainly applied to polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyester, ABS resin, epoxy resin, synthetic rubber antioxidant stabilizer for PVC vinyl products as chelating agent, when the metal is as based stabilizer, coordinating with the product can reduce the harm of metal chloride (6) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins. (7) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins. (8) Chelating agent, it is widely used in all kinds of PVC products, it can enable products to maintain its transparency and suppress color change, and it can increase the antioxidant and light and heat stability of the primary stabilizer. In addition, the product is also used for PE, PP, ABS, SBS and other products, and it can be used for pesticide intermediates. It can be used for synthetic alkyd resins and polyester materials and polyester resins. Triphenyl phosphite (TPP) is the chemical compound with the formula P(OC6H5)3. This colourless viscous liquid is the ester of phosphorous acid and phenol. It is used as a ligand in organometallic chemistry. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation of alkenes. Chemical intermediate, stabilizer systems for resins, metal scavenger, diluent for epoxy resins. Stabilizer/antioxidant for vinyl plastics and polyethylene, polypropylene, styrene copolymers, and rubber. Triphenyl phosphite can be used:As a source of phosphorus and as a ligand for the synthesis of transition metal phosphide nanoparticles via heating-up process.To convert alcohols to alkyl halides.As a peptide coupling agent.As a low-temperature source of singlet oxygen after forming an adduct with ozone.To synthesize bromotriphenoxyphosphonium bromide, a brominating agent, by reacting with bromine.

Technology Process of Triphenyl phosphite

There total 42 articles about Triphenyl phosphite 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: 100.0%

phenol (108-95-2,27073-41-2) → triphenyl phosphite (101-02-0)

Guidance literature:

With Hexamethylphosphorous triamide; In toluene; at 130 ℃; for 8h; regioselective reaction; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1039/d0cc02889d

Reference yield: 100.0%

triphenylphosphite-borane complex → triphenyl phosphite (101-02-0)

Guidance literature:

With tert-butyl alcohol; 4 A molecular sieve; In tetrahydrofuran; at 25 ℃; for 72h;

DOI:10.1246/bcsj.77.1931

Reference yield: 85.5%

methanol (67-56-1) + phosphorus trichloride (7719-12-2,52843-90-0) → triphenyl phosphite (101-02-0) + dimethyl phenylphosphonite (18351-42-3) + diphenyl methylphosphonate (7526-26-3)

Guidance literature:

phosphorus trichloride; phenol; at 65 - 250 ℃; for 3 - 4h;

methanol; methyl iodide; at 210 - 250 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

phenol

2,4-dichloro-1,3-diphenyl-cyclodiphosphazane

Diphenyl phosphorochloridite

diphenyl bromophosphite

Downstream raw materials:

phenyl hippurate

4-aminopyridine

benzyl-triphenoxy-phosphonium; bromide

ethyl-triphenoxy-phosphonium; iodide

Refernces

• 1、 Wovkulich, Michael J.,Atwood, Jim D.. "LIGAND DISSOCIATION FROM MONO-SUBSTITUTED DERIVATIVES OF HEXACARBONYLCHROMIUM (Cr(CO)5L, L = P(C6H5)3, P(C4H9)3, P(OCH3)3, P(OC6H5)3, AND As(C6H5)3)". . p. 77 - 89. Retrieved 1980.
• 2、 Noack. "-". . p. 96. Retrieved 1883.
• 3、 Oae et al.. "-". . p. 549,551,553. Retrieved 1972.
• 4、 Rusik, C.A.,Collins, M.A.,Gamble, A.S.,Tonker, T.L.,Templeton, J.L.. "Reactions of η2-Acyl Ligands in Tp'(CO)2Mo2-C(O)R> Complexes To Form Complexed Enolates and Enones, Allyls, and Alkyne Insertion Products". . p. 2550 - 2560. Retrieved 1989.
• 5、 Lee, Keng Lung,Feld, Joey,Hume, Paul,S?hnel, Tilo,Leitao, Erin. "The Synthesis and Mechanistic Considerations of a Series of Ammonium Monosubstituted H-Phosphonate Salts". . p. 815 - 824. Retrieved 2021.
• 6、 Ogata et al.. "-". . p. 3709. Retrieved 1974.
• 7、 Budnikova, Yu. G.,Kargin, Yu. M.,Zaripov, I. M.,Romakhin, A. S.,Ignat'ev, Yu. A.,et al.. "ELECTROCHEMICALLY INDUCED PROCESSES OF FORMATION OF PHOSPHORUS ACID DERIVATIVES. 4. SYNTHESIS OF TRIALKYL PHOSPHATES FROM WHITE PHOSPHORUS". . p. 1585 - 1588. Retrieved 1992.
• 8、 Zhang, Yue,Cai, Ziman,Chi, Yangyang,Zeng, Xiangzhe,Chen, Shuanghui,Liu, Yan,Tang, Guo,Zhao, Yufen. "Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus". supporting information. p. 5158 - 5163. Retrieved 2021/07/20.
• 9、 Walczak, Maciej,Chryplewicz, Agnieszka,Olewińska, Sandra,Psurski, Mateusz,Winiarski, ?ukasz,Torzyk, Karolina,Oleksyszyn, Józef,Sieńczyk, Marcin. "Phosphonic Analogs of Alanine as Acylpeptide Hydrolase Inhibitors". . . Retrieved 2021/02/01.