Triphenylphosphine

HCID 11776CAS 603-35-0

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

TRIPHENYLPHOSPHINE603-35-0TriphenylphosphaneTriphenyl phosphinePhosphine, triphenyl-TriphenylphosphorusTriphenylphosphideTrifenylfosfinPP 360DTXSID5026251NSC-1026D26OA393
Show more names
PPh3TriphenylTriphenyphosphineriphenylphosphineTriphenyl phospinetptbp
NSC-215203DTXCID906251CHEBI:183318RefChem:6333210-036-0Triphenylphosphine resintriphenyl-phosphane39319-11-4

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phosphorus Compounds
SpringerMaterials PropertiesSchoenflies notation
LogP5.69
OdorODORLESS
Density · 4 items

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 · 2 items

MONOCLINIC PLATELETS OR PRISMS FROM ETHER

WHITE CRYSTALLINE SOLID

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)

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 4 items

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

Other Safety InformationIMAP assessments - Phosphine, triphenyl-: Human health tier II assessment
DOT LabelClass 9
Fire Hazards · 2 items

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 HazardsACUTE/CHRONIC HAZARDS: Toxic; when heated to decomposition, emits highly toxic fumes of phosphine and POx. (NTP, 1992)
Hazards Summary · 1 item

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 · 2 items

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 · 4 items

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 · 1 item

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 StorageSeparated from oxidants and acids. Keep in a well-ventilated room.
Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting ProceduresFOAM MAY CAUSE FROTHING.

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat.

Redness.

Redness. Pain.

Cough.

ICSC Environmental DataBioaccumulation of this chemical may occur in the environment.
Non-Human Toxicity Excerpts · 3 items

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.

Toxicity DataLC50 (rat) = 1,135 ppm/4h

Safety data

F
9
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
SZ3500000
ridadr
3077

Chemistry & industry

Uses & manufacturing

Uses · 4 items

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 · 2 items

(1977) No Data

(1979) No Data

U.S. Imports · 2 items

(1977) 2.72X10+7 G (PRINCPL CUSTMS DISTS)

(1979) 7.58X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production · 3 items

2023: 1,000,000 - <2,500,000 lb

(1977) No Data

(1979) No Data

Consumer UsesCatalyst
Industry UsesCatalyst
Applications · 3 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

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