triphenyl-λ5-phosphanethione

• ChemBase ID: 83015
• Molecular Formular: C18H15PS
• Molecular Mass: 294.350461
• Monoisotopic Mass: 294.06320811
• SMILES: P(=S)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: S=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C18H15PS/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
• InChIKey: VYNGFCUGSYEOOZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl-λ^5-phosphanethione; triphenyl-$l^{5}-phosphanethione
• IUPAC Traditional name: triphenyl-λ^5-phosphanethione; triphenylphosphine sulfide
• Synonyms: Triphenylphosphine sulfide; Triphenylthioxophosphorane; Triphenylphosphine sulfide; triphenylphosphine sulphide; 三苯基膦硫; 三苯基硫化膦

Database IDs

• CAS Number: 3878-45-3
• EC Number: 223-407-7
• MDL Number: MFCD00004917
• Beilstein Number: 645872
• PubChem SID: 24848200; 162070134; 24889796
• PubChem CID: 19758
• Chemspider ID: 18610
• Wikipedia Title: Triphenylphosphine_sulfide

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.4894
• LogD (pH = 7.4): 5.4894
• Log P: 5.4894
• Molar Refractivity: 91.0567 cm^3
• Polarizability: 36.259323 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: dichloromethane, ethanol
• Apperance: white solid
• Melting Point: 158-164°C; 161-163 °C; 161-163 °C(lit.)

Safety Information

• RTECS: SZ2820000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: UN3464
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/21/22-36/37/38; 21/22-36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H335; H331-H302-H312-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC); 98%
• Grade: purum
• Linear Formula: (C6H5)3PS

DETAILS

Sigma Aldrich - 135100

Packaging
5, 25 g in glass bottle

REFERENCES

• In the presence of TFA, converts epoxides to episulfides (thiiranes) of the same stereochemistry: J. Am. Chem. Soc., 94, 2880 (1972).
• The Pd-catalyzed bisalkoxycarbonylation of olefins gives improved yields in the presence of triphenylphosphine sulfide as a ligand. The phosphine oxide and selenide were significantly less effective, and no product was obtained with triphenylphosphine itself: Tetrahedron Lett, 39, 7529 (1998):