Triphenylphosphine
PPh3 · Triphenylphosphane · Triphenyl phosphine · Triphenyl · Triphenyphosphine · triphenyl-phosphane · riphenylphosphine · TRIPHENYLPHOSPHORUS
Identifiers & Physical Properties
| CAS No. | 603-35-0 |
|---|---|
| Molecular formula | C18H15P |
| Average molar mass | 262.3 g/mol |
| Monoisotopic mass | 262.09113711 g/mol |
| SMILES | c1ccc(P(c2ccccc2)c2ccccc2)cc1 |
| InChIKey | RIOQSEWOXXDEQQ-UHFFFAOYSA-N |
| PubChem CID | 11776 |
| ChEMBL | CHEMBL1448331 |
| ChEBI | CHEBI:183318 |
| EC No. | 210-036-0 |
| DTXSID | DTXSID5026251 |
Chemical & Physical Properties
| XLogP | 4.6 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 3 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 202 |
| Chemical classes | Other Classes -> Phosphorus Compounds |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (partition coefficient) | 5.69 |
| Odor | ODORLESS |
| Density | 1.194 at 77 °F (NTP, 1992) - Denser than waterwill sink1.075 @ 80 °C/4 °C1.1 g/cm³1.194 @25 °C1.132 |
| Color/Form | MONOCLINIC PLATELETS OR PRISMS FROM ETHERWHITE CRYSTALLINE SOLID |
| Solubility | Insoluble (NTP, 1992)FREELY SOL IN ETHERSOL IN BENZENE, CHLOROFORM, GLACIAL ACETIC ACIDLESS SOL IN ALCOHOLPRACTICALLY INSOL IN WATERSOL IN CARBON TETRACHLORIDESolubility in water, mg/l at 25 °C: 0.09 (very poor)water: soluble0.00017 g/L at 22°C |
| Flash point | 356 °F (NTP, 1992)180 °C OC.182 °C c.c.181 °C |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Boiling point | greater than 680 °F at 760 mmHg (NTP, 1992)MORE THAN 360 °C377 °C377 °C(lit.) |
| Melting point | 176 °F (NTP, 1992)80.5 °C80 °C79 °C79-81 °C(lit.) |
| Vapor pressure | Vapor pressure, Pa at 50 °C: 0.0175 mm Hg ( 20 °C) |
| Bulk density | 500-600kg/m3 |
| Vapor density | 9 (vs air) |
| Refractive index | 1.6358 |
| Storage conditions | Store below +30°C. |
| Physical state | Crystals, Crystalline Powder or Flakes |
| Specific gravity | 1.132 |
| Color | White |
| Specific heat capacity | Cp(crystal): 1.19 J/(g·K), at 25℃ |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| Merck | 14,9743 |
| BRN | 610776 |
| Henry's law constant | 4.3×102 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| Stability | Stable. Incompatible with oxidizing agents, acids. |
| Cosmetics Ingredients Functions | NAIL CONDITIONING |
| 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 |
| InChIKey | RIOQSEWOXXDEQQ-UHFFFAOYSA-N |
| SMILES | c1ccc(cc1)P(c2ccccc2)c3ccccc3 |
| CAS DataBase Reference | 603-35-0(CAS DataBase Reference) |
| FDA UNII | 26D26OA393 |
| NIST Chemistry Reference | Phosphine, triphenyl-(603-35-0) |
| EPA Substance Registry System | Triphenylphosphine (603-35-0) |
| UNSPSC Code | 12352128 |
| NACRES | NA.22 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H302-H315-H319-H372-H317-H335-H413 |
| GHS precautionary statements | P501-P273-P272-P260-P270-P271-P264-P280-P302+P352-P314-P337+P313-P305+P351+P338-P362+P364-P333+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405 |
| Target organs | Central nervous system,Peripheral nervous system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Hazard symbols | Xn,N |
| Risk statements (R) | 22-43-53-50/53-48/20/22 |
| Safety statements (S) | 36/37-60-61-36/37/39-26 |
| UN transport number | 3077 |
| Water hazard class (WGK) | 2 |
| RTECS number | SZ3500000 |
| F | 9 |
| Autoignition temperature | 425 °C |
| TSCA inventory status | TSCA listed |
| Customs code | 29310095 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazard class | Acute Tox. 4 OralEye Dam. 1Skin Sens. 1BSTOT RE 1 Inhalation |
| Hazardous substances data | 603-35-0(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.5% (6 of 1290) of reports.DangerH302 (97.1%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P319, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1290 reports by companies from 56 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Phosphine, triphenyl-Phosphine, triphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphine, triphenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 14-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13659Triphenylphosphine: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Phosphine, triphenyl-: Human health tier II assessment |
| DOT label | Class 9 |
| Fire hazards | This compound is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Health hazards | ACUTE/CHRONIC HAZARDS: Toxicwhen heated to decomposition, emits highly toxic fumes of phosphine and POx. (NTP, 1992) |
| Hazards summary | Decomposed by heating forming phosphine and phosphorous oxidesA skin, eye, and respiratory tract irritant[ICSC] Causes convulsions at lethal doses in animal experiments[RTECS] A strong reducing agent[CAMEO] Harmful if ingestedMay cause skin sensitization[Aldrich MSDS] See Phosphine. |
| Reactive group | Amines, Phosphines, and Pyridines |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | TRIPHENYL PHOSPHINE reacts vigorously with oxidizing materials. (NTP, 1992). |
| Chemical Dangers | Decomposes on heating. This produces highly toxic fumes of phosphorus oxides and phosphine. Reacts with strong acids and strong oxidants. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Air and Water Reactions | Triphenylphosphine is a flammable solid which slowly oxidizes in air to form triphenylphosphine oxide. It is insoluble in water. |
| Fire fighting | Fires involving this chemical can be controlled with dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)Use water spray, foam, powder, carbon dioxide. |
| First aid measures | Fresh air, rest. Refer for medical attention.Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.Rinse mouth. Refer for medical attention . |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Safe storage | Separated from oxidants and acids. Keep in a well-ventilated room. |
| Exposure control and personal protection | 2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)] |
| Fire fighting procedures | FOAM MAY CAUSE FROTHING. |
| 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 °C. ODOR WAS REMOVED IN 4 HR VS 8 @ PH 8.5. |
| Nonfire spill response | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Spillage disposal | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Eye Prevention | Wear safety goggles or face shield. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| Exposure routes | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Signs and Symptoms | Cough. Sore throat.Redness.Redness. Pain. |
| ICSC Environmental Data | Bioaccumulation of this chemical may occur in the environment. |
| Non-Human Toxicity Excerpts | CNS EFFECTS: WEAKNESS & ATAXIA ONLY SYMPTOMS. IRRITANT EFFECTS: SLIGHT SKIN IRRITANT IN GUINEA PIG. /FROM TABLE/DURING INHALATION EXPOSURE MALE CHR-CD RATS SHOWED MILD RESP IRRITATIONSEVERE WT LOSS OCCURRED IMMEDIATELY AFTER EXPOSURE, FOLLOWED BY NORMAL RATE OF WT GAIN. MILD WT LOSS OCCURRED DURING 10-DAY EXPOSURE PERIOD, FOLLOWED BY NORMAL WT GAIN.Triphenylphosphine (TPP) was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. TPP was tested over a wide range of doses (0, 89, 285, 854, 2733 and 8200 ug/plate) in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. TPP was negative in these tests and the highest ineffective dose level tested (not causing formation of a precipitate) in any Salmonella tester strain was 89 ug/plate. |
| Toxicity Data | LC50 (rat) = 1,135 ppm/4h |
| F | 9 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | SZ3500000 |
| UN transport number | 3077 |
| Customs code | 29310095 |
| Toxicity | LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg |
| Risk statements (R) | 22-43-53-50/53-48/20/22 |
| Signal word | Danger |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xn,N |
| Safety statements (S) | 36/37-60-61-36/37/39-26 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Target organs | Central nervous system,Peripheral nervous system |
| GHS hazard statements | H302-H315-H319-H372-H317-H335-H413 |
| REACH registrations | Active |
| Hazard class | Acute Tox. 4 OralEye Dam. 1Skin Sens. 1BSTOT RE 1 Inhalation |
| Autoignition temperature | 425 °C |
| GHS precautionary statements | P501-P273-P272-P260-P270-P271-P264-P280-P302+P352-P314-P337+P313-P305+P351+P338-P362+P364-P333+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405 |
| Hazardous substances data | 603-35-0(Hazardous Substances Data) |
Applications & Uses
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.
Description
Triphenylphosphine: a member of tertiary phosphines Triphenylphosphine (TPP) is a member of tertiary phosphines, which is phosphane, in which the three hydrogens are replaced by phenyl groups. It has a role as a reducing agent and an NMR chemical shift reference compound. It is a crucial ligand utilized in the Wittig reaction for alkene synthesis. This reaction involves the formation of alkyliden-etriphenylphosphoranes from the action of butyllithium or another base on the quarternary halide. Triphenylphosphine is used to synthesise organic compounds due to its nucleophilicity and reducing character.
Uses
Triphenylphosphine is a versatile and efficient compound with a wide range of applications. It serves as a crucial ligand in homogeneous catalysts for petrochemical and fine chemical production, and as a co-catalyst in the production of isobutanol and n-butanol. It is also the basic raw material for rhodium phosphine complex catalysts, such as Wilkinson's catalyst (RhCl(PPh3)3) for alkene hydrogenation and tetrakis(triphenylphosphine)palladium(0) for C-C coupling reactions in organic synthesis. In the dye industry, it is utilized as a sensitizer, heat stabilizer, light stabilizer, antioxidant, flame retardant, antistatic agent, rubber antiozonant, and analytical reagent. The rhodium and triphenylphosphine catalyst system is employed in the hydroformylation of vegetable oils and their methyl esters, and polymer-supported triphenylphosphine catalyzes the γ-addition of pronucleophiles to alkynoates. It also participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids. Triphenylphosphine can be sulfonated to form trisulfonic acid and is used in Wittig synthesis as a standard ligand in homogeneous catalysis. It is involved in the synthesis of trimethyl phosphite, leading to the production of organophosphorus pesticides like dichlorvos, monocrotophos, and phosphamidon. Furthermore, it is used as a stabilizer in rubber and resin synthesis, an antioxidant in polyvinyl chloride, and a raw material in the synthesis of alkyd resins and polyester resins. Triphenylphosphine is also used in the synthesis of Chlorambucil, a cytotoxic agent for breast and pancreatic cancers, and in the preparation of α-Tocopherol analogues for monitoring antioxidant status.