triphenylphosphane

• ChemBase ID: 92455
• Molecular Formular: C18H15P
• Molecular Mass: 262.285461
• Monoisotopic Mass: 262.09113711
• SMILES: P(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenylphosphane
• IUPAC Traditional name: triphenylphosphine
• Synonyms: Triphenyl phosphine; TRIPHENYLPHOSPHINE; Trisphenylphosphine; Phosphorustriphenyl; Triphenylphosphine; TPP; Triphenylphosphine, flake; Triphenylphosphine, powder; 三苯基膦; 三苯膦; 三苯基瞵; 三苯基膦, 片状; 三苯基膦, 粉末

Database IDs

• CAS Number: 603-35-0
• EC Number: 210-036-0
• MDL Number: MFCD00003043
• Beilstein Number: 610776
• Merck Index: 149743
• PubChem SID: 24889789; 162079153; 24900530
• PubChem CID: 11776
• Chemspider ID: 11283
• Wikipedia Title: Triphenylphosphine

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• Molar Refractivity: 81.6229 cm^3
• Polarizability: 32.34495 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Insoluble in water; Insoluble in water. Soluble in benzene, acetone, carbon tetrachloride, ether, and glacial acetic acid; organic solvents
• Apperance: Flake; White Solid
• Melting Point: 77-84 °C; 78°C; 78-82°C; 79-81 °C; 79-81 °C(lit.); 79-81°C; 80°C
• Boiling Point: 360°C; 360°C; 377 °C(lit.); 377°C
• Flash Point: 180 °C; 181°C; 181°C(358°F); 356 °F
• Density: 1.1 g cm^-3, solid; 1.194 g/ml; 1.20; 1.200
• Refractive Index: 1.59; ε_r, etc.
• Vapor Pressure: 5 mmHg ( 20 °C)
• Vapor Density: 9 (vs air)

Safety Information

• Storage Warning: Toxic/Harmful/Irritant
• RTECS: SZ3500000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-43-48/20/22; 22-43-53; R:22; R20 R22 R40 R43 R50 R53
• Safety Statements: 22-24-37-45; 24-37-61; S:36/37/39; S36 S37 S45 S57 S60
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317-H373; H302-H317-H413
• GHS Precautionary statements: P261-P280-P302+P352-P321-P301+P312-P501A; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target Organ: Nervous system

Product Information

• Purity: ≥95.0% (GC); ≥98.5% (GC); 97%; 98%; 99%; 99+%
• Grade: puriss.; ReagentPlus®
• Impurities: ~1% triphenylphosphine oxide; ~3% triphenylphosphine oxide
• Linear Formula: (C6H5)3P

DETAILS

Sigma Aldrich - 93092

Packaging
1 kg in poly bottle
250 g in poly bottle

Sigma Aldrich - T84409

Packaging
1 kg in poly bottle
1, 25, 100, 500 g in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• In suitable circumstances, the iminophosphorane may undergo intramolecular aza-Wittig reaction: Tetrahedron, 45, 6375 (1989):
  
• Reviews: Aza-Wittig reaction in heterocyclic synthesis: Org. Prep. Proced. Int., 24, 209 (1992); Iminophosphoranes as building blocks for the preparation of N-containing heterocycles: Synthesis, 1197 (1994).
• For use in the Mitsunobu reaction for conversion of alcohols to alkylating agents, see N-Guanylurea sulfate, A19106, and Diisopropyl azodicarboxylate, L10386. See also 1,2-Bis(diphenylphosphino)ethane, A11419.
• Finds widespread use as a complexing agent with transition metals, either in the preparation of stable complexes, or as an additive in metal-promoted reactions. See also Tri(o-tolyl)phosphine, A12093 and Tri(2-furyl)phosphine, L13329.
• Azides can be converted selectively to amines, in the presence of ester, epoxide or nitro groups, by reduction to iminophosphoranes (Staudinger reaction), followed by hydrolysis. For reviews, see: Tetrahedron, 37, 437 (1981); 48, 1353 (1992):
  
• For use in peptide and other coupling reactions, see 2,2'-Dipyridyl disulfide, A11118.