Basic information
- Standard SMILES
O=P(c1ccccc1)(c1ccccc1)c1ccccc1- InChIKey
FIQMHBFVRAXMOP-UHFFFAOYSA-N- Molecular formula
- C18H15OP
- Average molar mass
- 278.3 g/mol
- Monoisotopic mass
- 278.0860521
Names & identifiers
- Preferred name
- Triphenylphosphine Oxide
- IUPAC
- diphenylphosphorylbenzene
- English name
- Triphenylphosphine oxide
- Molecular formula
- C18H15OP
- Molecular weight
- 278.28
Names & synonyms
TRIPHENYLPHOSPHINE OXIDE791-28-6Phosphine oxide, triphenyl-Triphenyl phosphine oxideTriphenyl phosphorus oxideDTXSID2022121TRIPHENYLPHOSPHINE MONOXIDEZ69161FKI3phosphorane, triphenyl-, oxideDTXCID402121NSC-398RefChem:191910
Show more names
TPOTTPO(C6H5)3P=OOrlistat Related CoMpound CTriphenylphosphinoxidTrisphenylphosphine oxide
212-338-8triphenylphosphane oxidediphenylphosphorylbenzeneTriphenylphosphineoxide(diphenylphosphoroso)benzeneTPPOPH3PONSC 398
Database identifiers
- CAS
791-28-6- PubChem CID
- 13097
- DTXSID
DTXSID2022121- ChEMBL
CHEMBL482091- ChEBI
CHEBI:36601- UNII
- Z69161FKI3
- EC Number
- 212-338-8
- Nikkaji
- J541J
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 281
Experimental & physicochemical properties
Physical DescriptionSolid; [IUCLID] Beige crystalline solid; [Aldrich MSDS]
Kovats Retention Index2561；2576
Collision Cross Section
162.9 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2022121]；163.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2022121]；182.6 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2022121]
Physicochemical properties
- Melting point
- 150 · 150-157 °C(lit.)
- Boiling point
- 360 °C · 360 °C
- Density
- 1 · 1,212 g/cm3
- bulk density
- 400 · 400-450kg/m3
- vapor pressure
- 1 hPa · <1 hPa (50 °C)
- Flash point
- 180 °C · 180 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 25 mg/mL, · methanol: 25 mg/mL, clear
- form
- Crystalline Powder or Flakes
- Specific Gravity
- 1.212 · 1.212
- color
- White to pink-brown
- Water Solubility
- slightly soluble
- Hydrolytic Sensitivity
- 4 · 4: no reaction with water under neutral conditions
- BRN
- 745854 · 745854
- Henry's Law Constant
- 1.9 · 1.9×104 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- Major Application
- pharmaceutical
- InChI
- 1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
- InChIKey
- FIQMHBFVRAXMOP-UHFFFAOYSA-N
- SMILES
- O=P(c1ccccc1)(c2ccccc2)c3ccccc3
- LogP
- 2.8 · 2.8
- CAS DataBase Reference
- 791 · 791-28-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 69161 FKI3 · Z69161FKI3
- NIST Chemistry Reference
- (C6H5)3PO(791-28-6)
- EPA Substance Registry System
- Triphenylphosphine oxide (791-28-6)
- UNSPSC Code
- 77101502 · 77101502
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Warning
- Hazard statements
- 290 · H290
- Precautionary statements
- 234 · P234-P390
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-52/53
- Safety Statements
- 26 · 26-61-36
- RIDADR
- 3077 · 3077
- WGK Germany
- 2 · 2
- RTECS
- 1676000 · SZ1676000
- Autoignition Temperature
- 590 °C · 590 °C
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 29310095 · 29310095
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3
- Toxicity
- 50 orally · LD50 orally in Rabbit: 685 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2% (5 of 245) of reports.
Warning
H302 (98%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (18%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (18.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (18%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H412 (96.3%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 245 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 5 of 245 reports by companies.；There are 11 notifications provided by 240 of 245 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: Phosphine oxide, triphenyl-
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 10-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25368；Status: Active Update: 05-09-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17507
Triphenylphosphine oxide: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes convulsions, aggression, and dyspnea in oral lethal-dose studies of dogs (LD50 = 500 mg/kg); [RTECS] Causes liver injury in 3-month feeding study of dogs at 2,000 ppm; [IUCLID] An irritant; Harmful by ingestion; Targets nerves; [Aldrich MSDS] See Triphenylphosphine.
Hazard Classes and Categories
Acute Tox. 4 (98%)；Skin Irrit. 2 (18%)；Eye Irrit. 2 (18.4%)；STOT SE 3 (18%)；Aquatic Chronic 3 (96.3%)
Acute toxicity (Oral) - Category 4；Specific target organ toxicity - Single exposure - Category 2 (central nervous system)；Specific target organ toxicity - Repeated exposure - Category 2 (liver)；Hazardous to the aquatic environment (Acute) - Category 3；Hazardous to the aquatic environment (Long-term) - Category 3
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin；Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
RAIS Toxicity Values
0.02
PPRTV Current
0.02
PPRTV Current
EPA Provisional Peer-Reviewed Toxicity Values
Triphenylphosphine Oxide
2 x 10^-2 mg/kg-day
2 x 10^-2 mg/kg-day
PDF Document
Inadequate information to assess carcinogenic potential
2007
Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06
1.30e+03
1.60e+04
3.60e+02
5.00e+01
1.50e+00
2.00e-02
Hazard Quotient Level 3 or Cancer Risk Level 1E-04
3.80e+03
4.90e+04
1.10e+03
5.00e+01
2.00e-02
Volatile
Regulatory information
Regulatory Information
Chemical: Phosphine oxide, triphenyl-
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 10-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25368；Status: Active Update: 05-09-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17507
Triphenylphosphine oxide: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SZ1676000
- ridadr
- 3077
- hs_code
- 29310095
- Toxicity
- LD50 orally in Rabbit: 685 mg/kg
- risk_code
- 22-36/37/38-52/53
- Signal word
- Warning
- Symbol(GHS)
- GHS05
- hazard_code
- Xn,Xi
- safety_code
- 26-61-36
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H290
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 3
- Autoignition Temperature
- 590 °C
- Precautionary statements
- P234-P390
Chemistry & industry
Uses & manufacturing
UsesUsed for processing (extraction, separation, and spectrophotometric determination) environmental samples of cadmium and mercury; [ChemIDplus]
General Manufacturing InformationPhosphine oxide, triphenyl-: ACTIVE
Applications
DescriptionTriphenylphosphine oxide (TPPO) is a coordinating solvent used to activate crystallization of chemical compounds. It has been used in flame retardant applications, as an epoxy cure catalyst, and more recently, to produce nanostructures.
UsesTriphenylphosphine Oxide (Orlistat USP Related Compound C) is a catalyst in the conversion of aldehydes into 1,1-dichlorides. Triphenylphosphine Oxide is used as a catalyst for the synthesis of hightly functionalized α-CF3 γ-keto esters.
UsesTriphenylphosphine oxide can be used:As a catalyst in Appel-type chlorination reaction of acyclic primary and secondary alcohols.As a catalyst in stereoselective poly and dibromination of α,β-unsaturated esters and β,γ-unsaturated α-ketoester compounds.As a promotor in the diastereoselective synthesis of α-ribofuranosides through ribofuranosylation of alcohols with ribofuranosyl iodides.
UsesTriphenylphosphine oxide is a phosphine ligand used for coupling reactions, epoxidations, and Michael reactions
Preparation methods
PreparationMany reactions in organic synthesis, such as the Wittig, Staudinger, and phototactic reactions, produce Ph3PO as a byproduct. Ph3PCl2 also produces triphenylphosphine oxide during the conversion of alcohols to chlorinated hydrocarbons: Ph3PCl2 + ROH → Ph3PO + HCl + RCl
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A phosphine oxide in which the substituents on phosphorus are three phenyl groups.
Related reactions
457 records
Linked notes
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