Basic information
- Standard SMILES
c1ccc(P(c2ccccc2)c2ccccc2)cc1- InChIKey
RIOQSEWOXXDEQQ-UHFFFAOYSA-N- Molecular formula
- C18H15P
- Average molar mass
- 262.3 g/mol
- Monoisotopic mass
- 262.09113711
Overview
Triphenyl phosphine appears as white crystals. (NTP, 1992)
Names & identifiers
- Preferred name
- Triphenylphosphine
- IUPAC
- triphenylphosphane
- English name
- Triphenylphosphine
- Molecular formula
- C18H15P
- Molecular weight
- 262.29
Names & synonyms
Show more names
Database identifiers
- CAS
603-35-0- PubChem CID
- 11776
- DTXSID
DTXSID5026251- ChEMBL
CHEMBL1448331- ChEBI
CHEBI:183318- UNII
- 26D26OA393
- EC Number
- 210-036-0
- Nikkaji
- J1.652G
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 202
Experimental & physicochemical properties
Density
1.194 at 77 °F (NTP, 1992) - Denser than water; will sink
1.075 @ 80 °C/4 °C
1.1 g/cm³
1.194 @25 °C
Color/Form
MONOCLINIC PLATELETS OR PRISMS FROM ETHER
WHITE CRYSTALLINE SOLID
Solubility
Insoluble (NTP, 1992)
FREELY SOL IN ETHER; SOL IN BENZENE, CHLOROFORM, GLACIAL ACETIC ACID; LESS SOL IN ALCOHOL; PRACTICALLY INSOL IN WATER
SOL IN CARBON TETRACHLORIDE
Solubility in water, mg/l at 25 °C: 0.09 (very poor)
Flash Point
356 °F (NTP, 1992)
180 °C OC.
182 °C c.c.
Boiling Point
greater than 680 °F at 760 mmHg (NTP, 1992)
MORE THAN 360 °C
377 °C
Melting Point
176 °F (NTP, 1992)
80.5 °C
80 °C
79 °C
Physicochemical properties
- Melting point
- 79 · 79-81 °C(lit.)
- Boiling point
- 377 °C · 377 °C(lit.)
- Density
- 1.132 · 1.132
- bulk density
- 500 · 500-600kg/m3
- vapor density
- 9 · 9 (vs air)
- vapor pressure
- 5 mm · 5 mm Hg ( 20 °C)
- refractive index
- 1.6358 · 1.6358
- Flash point
- 181 °C · 181 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.00017 g/L · water: soluble0.00017 g/L at 22°C
- form
- Crystals, Crystalline Powder or Flakes
- Specific Gravity
- 1.132 · 1.132
- color
- White
- Odor
- odorless
- Water Solubility
- Insoluble
- Specific Heat Capacity
- 1.19 J/ · Cp(crystal): 1.19 J/(g·K), at 25℃
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- Merck
- 14 · 14,9743
- BRN
- 610776 · 610776
- Henry's Law Constant
- 4.3 · 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 · 603-35-0(CAS DataBase Reference)
- FDA UNII
- 26 D26OA393 · 26D26OA393
- NIST Chemistry Reference
- Phosphine, triphenyl-(603-35-0)
- EPA Substance Registry System
- Triphenylphosphine (603-35-0)
- UNSPSC Code
- 12352128 · 12352128
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H319-H372-H317-H335-H413
- Precautionary statements
- 501 · 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
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,N
- Risk Statements
- 22 · 22-43-53-50/53-48/20/22
- Safety Statements
- 36 · 36/37-60-61-36/37/39-26
- RIDADR
- 3077 · 3077
- WGK Germany
- 2 · 2
- RTECS
- 3500000 · SZ3500000
- F
- 9 · 9
- Autoignition Temperature
- 425 °C · 425 °C
- TSCA
- TSCA listed
- HS Code
- 29310095 · 29310095
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Sens. 1BSTOT RE 1 Inhalation
- Hazardous Substances Data
- 603 · 603-35-0(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (6 of 1290) of reports.
Danger
H302 (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.
Danger
Hazard information
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/13659
Triphenylphosphine: Does not have an individual approval but may be used under an appropriate group standard
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.
Hazards Summary
Decomposed by heating forming phosphine and phosphorous oxides; A skin, eye, and respiratory tract irritant; [ICSC] Causes convulsions at lethal doses in animal experiments; [RTECS] A strong reducing agent; [CAMEO] Harmful if ingested; May cause skin sensitization; [Aldrich MSDS] See Phosphine.
Safety & protection
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.
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.
Toxicology
Signs and Symptoms
Cough. Sore throat.
Redness.
Redness. Pain.
Cough.
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 IRRITATION; SEVERE 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.
Safety data
- F
- 9
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SZ3500000
- ridadr
- 3077
- hs_code
- 29310095
- Toxicity
- LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg
- risk_code
- 22-43-53-50/53-48/20/22
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn,N
- safety_code
- 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
- Hazard statements
- H302-H315-H319-H372-H317-H335-H413
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1BSTOT RE 1 Inhalation
- Autoignition Temperature
- 425 °C
- 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)
Chemistry & industry
Uses & manufacturing
Uses
Used as a polymerization initiator and an intermediate to make pharmaceuticals, phosphonium salts, and other phosphorus compounds; [HSDB]
ORGANIC SYNTHESIS; POLYMERIZATION INITIATOR
SYNTHESIS OF PHOSPHONIUM SALTS, OTHER PHOSPHORUS COMPOUNDS
CHEMICAL INTERMEDIATE, EG, FOR PHARMACEUTICALS
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) 2.72X10+7 G (PRINCPL CUSTMS DISTS)
(1979) 7.58X10+7 G (PRINCPL CUSTMS DISTS)
U.S. Production
2023: 1,000,000 - <2,500,000 lb
(1977) No Data
(1979) No Data
Methods of Manufacturing
REACTION OF PHENYLMAGNESIUM BROMIDE AND PHOSPHORUS TRICHLORIDE
FROM PHENYLMAGNESIUM BROMIDE & PHOSPHORUS TRICHLORIDE: PFEIFFER, PIETSCH, BER 37, 4621 (1904); SAUVAGE COMPT REND 139, 675 (1904); DODONON, MEDOX, BER 61, 910 (1928); DENNEY ET AL, J AM CHEM SOC 83, 1729 (1961).
BY A MODIFIED GRIGNARD SYNTHESIS.
General Manufacturing Information
Synthetic Rubber Manufacturing
Phosphine, triphenyl-: ACTIVE
Applications
UsesTriphenylphosphine 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.
DescriptionTriphenylphosphine: 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.
UsesTriphenylphosphine 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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