tris(furan-2-yl)phosphane

• ChemBase ID: 75028
• Molecular Formular: C12H9O3P
• Molecular Mass: 232.171821
• Monoisotopic Mass: 232.02893078
• SMILES: P(c1ccco1)(c1ccco1)c1ccco1
• Canonical SMILES: c1coc(c1)P(c1ccco1)c1ccco1
• InChI: InChI=1S/C12H9O3P/c1-4-10(13-7-1)16(11-5-2-8-14-11)12-6-3-9-15-12/h1-9H
• InChIKey: DLQYXUGCCKQSRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(furan-2-yl)phosphane
• IUPAC Traditional name: tris(furan-2-yl)phosphane
• Synonyms: Tri(fur-2-yl)phosphane; Tris(fur-2-yl)phosphine; TFP; Tri-2-furanylphosphine; Tris(2-furanyl)phosphine; Tris(o-furyl)phosphine; Tri(2-furyl)phosphine; Tri(furan-2-yl)phosphine; Tri-2-furylphosphine; Tris(2-furyl)phosphine; Tri(2-furyl)phosphine; 三(2-呋喃基)膦

Database IDs

• CAS Number: 5518-52-5
• EC Number: 000-000-0
• MDL Number: MFCD00151857
• Beilstein Number: 1577564
• PubChem SID: 24887951; 24863985; 162039946
• PubChem CID: 521585

CALCULATED PROPERTIES

• Log P: 2.4873
• Molar Refractivity: 56.923 cm^3
• Polarizability: 22.853708 Å^3
• Polar Surface Area: 39.42 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.4873
• LogD (pH = 7.4): 2.4873

PROPERTIES

Physical Property

• Apperance: faintly brown
• Melting Point: 59-64 °C; 59-64 °C(lit.); 59-64°C; 59-64°C
• Boiling Point: 136 °C/4 mmHg(lit.); 136/mm°C; 136°C/4mm
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; Cycloisomerizations; Heck Reaction; Negishi Coupling; Oxidations; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: Irritant/Moisture Sensitive/Air Sensitive/Store under Nitrogen/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-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: ≥99.0% (GC); 97%; 98%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C12H9O3P

DETAILS

Sigma Aldrich - 383767

Packaging
1 g in glass bottle

Sigma Aldrich - 82163

Other Notes
Phosphine ligand for transition-metal-mediated org. synthesis1; Leads in Wittig reactions to improved (Z) selectivity2

Toronto Research Chemicals - T793700

A phopshine ligand used in transition-metal mediated organic synthesis, in particular in wittig reactions to improved (Z) selectivity.

REFERENCES

• Andersen N.G. et al.: Chem. Rev., 101, 997 (2001)
• Appel M. et al.: Eur. J. Org. Chem., 1143, (2001)
• Best ligand for Pd-catalyzed coupling of 5-iodouracil and unsaturated tributylstannanes: Synlett, 157 (1991).
• Large rate enhancements (10 ² -10 ³ ) over triphenylphosphine are observed in Pd-catalyzed coupling of olefinic stannanes and electrophiles: J. Am. Chem. Soc ., 113, 9585 (1991).
• In a study of Pd-catalyzed coupling reactions in supercritical CO ₂, this ligand was among the best tried in both the Stille and Heck reactions, giving much superior results to e.g. triphenyl- or tri(o-tolyl)phosphine: Chem. Commun., 1397 (1998). See also Tris[3,5-bis(trifluoromethyl)phenyl]phosphine, L06941.