Triphenylphosphine

HCID 178928520CAS 39319-11-4

Basic information

Standard SMILES
c1ccc(P(c2ccccc2)c2ccccc2)cc1
InChIKey
RIOQSEWOXXDEQQ-UHFFFAOYSA-N
Molecular formula
C18H15P
Average molar mass
262.3 g/mol

Overview

Triphenyl phosphine appears as white crystals. (NTP, 1992)

Names & identifiers

Preferred name
Triphenylphosphine
IUPAC
triphenylphosphane
English name
Triphenylphosphine resin
Molecular formula
C18H15P
Molecular weight
262.285461

Names & synonyms

TRIPHENYLPHOSPHINE603-35-0TriphenylphosphaneTriphenyl phosphinePhosphine, triphenyl-TriphenylphosphorusTriphenylphosphideTrifenylfosfinPP 360DTXSID5026251NSC-1026D26OA393
Show more names
POLYMER-BOUND TRIPHENYLPHOSPHINEPOLYMER SUPPORTED TRIPHENYLPHOSPHINEDIPHENYLPHOSPHINO-POLYSTYRENETRIPHENYLPHOSPHINE POLYSTYRENETRIPHENYLPHOSPHINE POLYMER BOUNDTRIPHENYLPHOSPHINE POL. BOUND, 100-200 M ESH, ~1.6 MMOL/GPL-TPP RESIN-C6H4P(C6H5)2PL-TPP MP-RESINPOLYSTYRENE-PPH2
NSC-215203DTXCID906251CHEBI:183318RefChem:6333210-036-0Triphenylphosphine resintriphenyl-phosphane39319-11-4

Database identifiers

CAS
39319-11-4
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
LogP · 2 items

5.69

5.69

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

storage temp.
2 · 2-8°C
form
Beads
color
White to yellow
Sensitive
Air Sensitive
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

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
10-23
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
hs_code
29310099
risk_code
22-43-20/21/22-36/37/38
Signal word
Warning

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 · 2 items

UsesPolymer-bound triphenylphosphine is a solid-supported reagent that can be used as a better alternative to triphenylphosphine in the Mitsunobu reaction.It can also be used:For the esterification of alkylphosphonic acids using primary alcohols in the presence of iodine and imidazole.To catalyze the conversion of 3-[3-(1,3-dioxolan-2-yl)-1-hydroxypropyl]pyridine to 3-[1-bromo-3-(1,3-dioxolan-2-yl)propyl]pyridine using carbon tetrabromide.To isomerize (Z)-nitro olefins to the (E)-isomers.To prepare polymer-bound ylides which are useful in Wittig reactions.To convert alcohols or carboxylic acids to the corresponding chlorides.In combination with carbon tetrachloride for the coupling N-alkoxycarbonyl α-amino acids and primary amines to form the corresponding amides.

UsesTriphenylphosphine resin is used for the preparation of polymer bound ylids which are useful for Wittig reactions.

Suppliers41 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
毕佳索(上海毕得医药科技股份有限公司)400-6005915 · [email protected]
湖北云镁科技有限公司027-59206672 18995657604 · [email protected]

Related reactions

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