Triphenylphosphine

Iupac Name：triphenylphosphane

Molecular Weight：262.285461

Modify Date.: 2022-11-07 22:13

Introduction: Triphenylphosphine (TPP) 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 vitamin synthesis and production of pharmaceutical active ingredients, crop protection products and coatings, TPP is used in synthesis of vitamin D2, vitamin A, clindamycin and other drugs. Besides it plays an important role in reactions of plant pigments.as an oxidation and UV stabilizer in plastics. In the dye industry, Triphenylphosphine is used as sensitizer, heat stabilizers, light stabilizers, antioxidants, flame retardants, antistatic agents, rubber antiozonants and analytical reagent.as an initiator of several polymerization reactions, The anionic phosphine is usually isolated as the trisodium salt which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions.It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds.As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides. View more+

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1. Names and Identifiers

1.1 Name: Triphenylphosphine
1.2 Synonyms: 4-16-00-00951 4-16-00-00951 (Beilstein Handbook Reference) bistriphenylphosphine diphenylenephenylphosphine EINECS 210-036-0 LPO Assay Triphenylphosphine MFCD00003043 Ph3P Phosphine, triphenyl- PHOSPHORUSTRIPHENYL PP-360 PPh3 tetrakistriphenylphosphine Trifenylfosfin Trihenylphosphine Triphenyl Triphenyl phosphine TRIPHENYL PHOSPHOROUS Triphenylphosphide triphenyl-phosphin Triphenyphosphine Trisphenylphosphine

1.3 CAS No.: 603-35-0

1.4 CID: 11776

1.5 EINECS(EC#): 210-036-0

1.6 Molecular Formula: C18H15P (isomer)

1.7 Inchi: InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

1.8 InChkey: RIOQSEWOXXDEQQ-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3

1.10 Isomers Smiles: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3

2. Properties

2.1 Density: 1.132

2.1 Melting point: 78.5-81.5℃

2.1 Boiling point: 377℃

2.1 Refractive index: 1.5918 (20 C)

2.1 Flash Point: 181℃

2.2 Precise Quality: 262.09100

2.2 PSA: 13.59000

2.2 logP: 3.44480

2.2 Solubility: water: soluble0.00017 g/L at 22°C

2.3 VaporDensity: 9 (vs air)

2.4 Appearance: White powder

2.5 Storage: Ambient temperatures.

2.6 Autoignition Temperature: 425 °C

2.7 Color/Form: MONOCLINIC PLATELETS OR PRISMS FROM ETHER
WHITE CRYSTALLINE SOLID

2.8 Odor: ODORLESS

2.9 Water Solubility: Insoluble

2.10 Spectral Properties: MAX ABSORPTION (DILUTED ALCOHOL): 260 NM (LOG E= 4.0); INDEX OF REFRACTION: 1.6358 @ 80 DEG C/D
IR: 5541 (Coblentz Society Spectral Collection)
UV: 6-768 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 8675 (Sadtler Research Laboratories Spectral Collection)
MASS: 208 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
IR: 2:1030A (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 10:69B (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
MASS: 4692 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

2.11 Stability: Stable. Incompatible with oxidizing agents, acids.

2.12 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Usage: Organic synthesis, polymerization initiator.

4. Safety and Handling

4.1 Symbol: GHS07, GHS08

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R43;R53

4.1 Safety Statements: S26;S36/37/39;S61

4.1 Packing Group: O52

4.1 Hazard Declaration: H302-H317-H373

4.1 Cleanup Methods: ALKALINE WASTEWATER (PH 11.7) CONTAINING 10 PPM PH3 FROM MFR OF TRIPHENYLPHOSPHINE TREATED WITH 30 PPM OF 0.15% H2O2 SOLN @ 25 DEG C. ODOR WAS REMOVED IN 4 HR VS 8 @ PH 8.5.

4.2 RIDADR: 3077

4.2 Fire Fighting Procedures: FOAM MAY CAUSE FROTHING.

4.3 Safety Profile: Moderately toxic byingestion. Mildly toxic by inhalation. A skinand eye irritant. Combustible when exposedto heat or flame. Slight explosion hazard inthe form of vapor when exposed to flame.Can react vigorously with oxidizingmaterials. To fight fire, use dry chemical,fog, CO2. When heated to decomposition itemits highly toxic fumes of phosphne andPOx. See also PHOSPHINE andPHENOL.

4.4 Caution Statement: P280

4.4 WGK Germany: 2

4.4 RTECS: SZ3500000

4.4 Safety: Hazard Codes:?Xn,?N
Risk Statements: 22-43-53-50/53-48/20/22?
R22:Harmful if swallowed.?
R43:May cause sensitization by skin contact.?
R53:May cause long-term adverse effects in the aquatic environment.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R48/20/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed and Harmful by inhalation.
Safety Statements: 36/37-60-61-36/37/39-26?
S36/37:Wear suitable protective clothing and gloves.?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3077
WGK Germany: 2
RTECS: SZ3500000
F: 9
HS Code: 29310095

4.5 Specification: ?Triphenylphosphine , its cas register number is 603-35-0. It also can be called?Phosphine, triphenyl- ; Trifenylfosfin ; Trifenylfosfin [Czech] ; Triphenyl phosphine .It?exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

4.6 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
chicken	LDLo	oral	9gm/kg (9000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014,
dog	LD50	oral	> 500mg/kg (500mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	National Technical Information Service. Vol. OTS0570648,
mouse	LD50	oral	1gm/kg (1000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014,
mouse	LD50	subcutaneous	3gm/kg (3000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014,
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat	LC50	inhalation	1135ppm/4H (1135ppm)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Annual Meeting of American Industrial Hygiene Association. Vol. -, Pg. -, 1969.
rat	LD50	intramuscular	1500mg/kg (1500mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014,
rat	LD50	oral	700mg/kg (700mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1B

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H373 May cause damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P314 Get medical advice/attention if you feel unwell.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

ESR : RED. OF MOO2(CYS-OET)2, 77K

ESR : RED. OF MOO2(CYS-OET)2, RT

ESR : VO(II)CL3 COMPLEX, POWDER, RT

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

1H NMR : parameter in benzene-d6

IR : CCl4 solution

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

603-35-0Total: 313 Synthesis Route

95-50-1 34 Suppliers

603-35-0 290 Suppliers

Literatures:
US4301301 A1, ;
Yield: null

791-28-6 223 Suppliers

603-35-0 290 Suppliers

Literatures:
Petit, Christelle; Poli, Evelyne; Favre-Reguillon, Alain; Khrouz, Lhoussain; Denis-Quanquin, Sandrine; Bonneviot, Laurent; Mignani, Gerard; Lemaire, Marc ACS Catalysis, 2013 , vol. 3, # 7 p. 1431 - 1438
Yield: ~99%

108-86-1 200 Suppliers

603-35-0 290 Suppliers

Literatures:
Cossairt, Brandi M.; Cummins, Christopher C. New Journal of Chemistry, 2010 , vol. 34, # 8 p. 1533 - 1536
Yield: ~70%

View all

8. Precursor and Product

precursor:

100-59-4

752-23-8

644-97-3

751-35-9

591-50-4

960-71-4

591-51-5

95-50-1

462-06-6

108-90-7

603-32-7

108-86-1

3605-36-5

791-28-6

View all

product :

645-49-8

6396-08-3

1034-39-5

768-03-6

5032-71-3

896-89-9

1449-46-3

680-31-9

900-92-5

1073-47-8

829-85-6

531-59-9

734-59-8

6399-81-1

484-12-8

644-97-3

7343-26-2

672-66-2

6396-07-2

3497-00-5

2049-55-0

6933-17-1

824-72-6

5293-84-5

791-28-6

View all

9. Other Information

9.0 Merck: 14,9743

9.1 BRN: 610776

9.2 description

Triphenylphosphine (TPP) 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 vitamin synthesis and production of pharmaceutical active ingredients, crop protection products and coatings, TPP is used in synthesis of vitamin D2, vitamin A, clindamycin and other drugs. Besides it plays an important role in reactions of plant pigments.
as an oxidation and UV stabilizer in plastics. In the dye industry, Triphenylphosphine is used as sensitizer, heat stabilizers, light stabilizers, antioxidants, flame retardants, antistatic agents, rubber antiozonants and analytical reagent.
as an initiator of several polymerization reactions, The anionic phosphine is usually isolated as the trisodium salt which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions.
It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds.
As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides.

View all

9.3 Chemical properties: This product is colorless to pale yellow monoclinic crystal below the room temperature, colorless to pale yellow transparent oily liquid above the room temperature with skin irritation and a pungent odour. Its mp about 22 ℃and bp 360 ℃(0.1 MPa) , n25D of 1.589 and relative density of 1.184 (20 ℃). And it is miscible with alcohol, ether, benzene and acetone and other organic solvents, while insoluble in water.

9.4 Name Reactions

Mitsunobu reactions
The triphenylphosphine combines with DEAD to generate a phosphonium intermediate that binds to the alcohol oxygen, activating it as a leaving group. Substitution by the carboxylate, mercaptyl, or other nucleophile completes the process.
Ozonolysis reactions
Ozonolysis allows the cleavage of alkene double bonds by reaction with ozone. Depending on the work up, different products may be isolated: reductive work-up gives either alcohols or carbonyl compounds, while oxidative work-up leads to carboxylic acids or ketones.
Staudinger reactions
Triphenylphosphine reacts with the azide to generate a phosphazide, which loses N2 to form an iminophosphorane. Aqueous work up leads to the amine and the very stable phosphine oxide.
Appel reactions
The reaction of triphenylphosphine and tetrahalomethanes (CCl4, CBr4) with alcohols is a ready method to convert an alcohol to the corresponding alkyl halide under mild conditions. The yields are normally high.
This reaction is somewhat similar to the Mitsunobu Reaction, where the combination of a phosphine, a diazo compound as a coupling reagent, and a nucleophile are used to invert the stereochemistry of an alcohol or displace it.

Name Reactions (Mitsunobu Ozonolysis Staudinger Appel reactions)

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9.5 Friedel-krogh`s method: The optimum reaction conditions: catalyst dosage 48g, reaction time 8h, the reaction temperature 400 ℃, the yield 63.5%. After sulfur, phosphorus trichloride and benzene reflux reacted directly, the generated triphenyl phosphine sulfide compound were deoxidized into triphenylphosphine by iron powder.

9.6 Uses: 1. In pesticide industry, 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.
2. Used in organic synthesis, polymerization initiator, raw materials of antibiotic drugs clindamycin, standard samples in organic trace analysis determination of phosphorus.
3. Widely used in pharmaceutical, petrochemical, paint, rubber and other industries, as catalyst, accelerator, flame retardant, heat and light stabilizer, lubricant, antioxidant etc.
4. In organic synthesis, such as synthesis of phosphorus salts and other phosphorus compounds.

9.7 Production methods: In this preparation method, phenol and phosphorus trichloride was used as raw materials. After esterification and vacuum distillation, the product namely triphenyl phosphite can be obtained.
3C6H5OH + PCl3 [15~20 ℃] → (C3H5O) 3P + 3HCl
Specific process can be classified into batch and continuous processes.
(1) Batch process
The phenol was added into the reactor, after warming to melt phosphorus trichloride was added to react with phenol at 70~90 ℃. After the phosphorus trichloride addition was completed, the temperature of reaction mixture was raised to about 150 ℃. After the removal of hydrogen chloride and unreacted phenol dissolved under reduced pressure at a high temperature, the product can be achieved.
(2) The use of a tower reactor
Phenol was feeding under the condenser located in the upper portion of the tower, while phosphorus trichloride enters above the receptacle located in the lower portion of the tower. Both reacted in the tower, and the product was collected in the receiver, meanwhile by-product hydrogen chloride was introduced into the absorber tower via the upper end of the condenser. After some process of the crude ester such as distillation, the product can be obtained.

9.8 Hazards & Safety Information: Category: toxic substances
Toxicity degree: grading poisoning
Acute toxicity: oral-rat LD50: 700 mg/kg; Oral-Mouse LD50: 1000 mg/kg
Skin irritation Data: rabbit 500 mg/24 hours severe; Eyes-rabbit 500 mg/24 hr mild
Flammability hazard characteristics: thermal decomposition into toxic phosphide
Storage characteristics: ventilated, low-temperature and dry storehouse; stored and transported separately with food raw materials
Extinguishing agent: carbon dioxide, sand, water, foam

9.9 Chemical Properties: White, crystalline solid. Insoluble inwater; slightly soluble in alcohol; soluble in benzene, acetone, carbon tetrachloride. Combustible.

9.10 Uses: PTC catalyst

9.11 Uses: 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.

9.12 Uses: In organic synthesis; polymerization initiator.

9.13 Production Methods: Manufactured from phenylmagnesium bromide and phosphorus trichloride.

9.14 Synthesis Reference(s): Tetrahedron Letters, 35, p. 625, 1994 DOI: 10.1016/S0040-4039(00)75855-2

9.15 General Description: Rhodium and triphenylphosphine catalyst system has been used for the hydroformylation of soybean, safflower and linseed oils and their methyl esters. Polymer supported triphenylphosphine has been reported to efficiently catalyze the γ-addition of pronucleophiles to alkynoate. Triphenylphosphine reacts with hydrated ruthenium trichloride in methanol to afford [RuCl₂(PPh₃)₄], [RuCl₂(PPh₃)₃] and [RuCl₃(PPh₃)₂CH₃OH]. It participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids.

9.16 Usage: Triphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides. The anionic phosphine is usually isolated as the trisodium salt which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions. It is also 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.

9.17 Usage: Triphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides. The anionic phosphine is usually isolated as the trisodium salt, which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions. It is also 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 catalyse C-C coupling reactions in organic synthesis.

9.18 Usage: In the synthesis of organic compounds, phosphonium salts and other phosphorus compounds, and as a polymerization initiatorTriphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides. The anionic phosphine is usually isolated as the trisodium salt, which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions. It is also 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 catalyse C-C coupling reactions in organic synthesis.

10. Computational chemical data

Molecular Weight: 262.285461g/mol
Molecular Formula: C₁₈H₁₅P
Compound Is Canonicalized: True
XLogP3-AA: 4.6
Exact Mass: 262.091137476
Monoisotopic Mass: 262.091137476
Complexity: 202
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 19
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB4AAIAAAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAAABUAAAGAgAAAAACACAEAAwAIAAACCAACBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What is the influence of added triphenylphosphine on the rate of hydroformylation catalysed by [Rh(CO) H (PPH3) 3]? Oct 18 2021
What does Le Chatelier’s principle state? If Rhodium is already complexed to three triphenylphosphine molecules, would it cause ligand exchange or improve the reaction? That depends on what is produced. There are two main transition metals that catalyze the reaction you are are mentioning. Co (cob...
Does triphenylphosphine show resonance? Jul 21 2021
The lone pair of phosphorus and the double bonds in benzene looks to be in conjugation. Do the molecule show resonance? If so, how?
Applications of Triphenylphosphine Feb 04 2021
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5 ) 3 - often abbreviated to PPh 3 or Ph 3 P. It is widely used in the synthesis of organic and organometallic compounds. PPh 3 exists as relatively air stable, colorless crystals at r...

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