tris(4-chlorophenyl)phosphane

• ChemBase ID: 82993
• Molecular Formular: C18H12Cl3P
• Molecular Mass: 365.620641
• Monoisotopic Mass: 363.97422005
• SMILES: P(c1ccc(cc1)Cl)(c1ccc(cc1)Cl)c1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)P(c1ccc(cc1)Cl)c1ccc(cc1)Cl
• InChI: InChI=1S/C18H12Cl3P/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18/h1-12H
• InChIKey: IQKSLJOIKWOGIZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(4-chlorophenyl)phosphane
• IUPAC Traditional name: tris(4-chlorophenyl)phosphane
• Synonyms: TRIS(4-CHLOROPHENYL)PHOSPHINE; tri(4-chlorophenyl)phosphine; NSC 136459; Tris(p-chlorophenyl)phosphine; Tris(4-chlorophenyl)phosphine; 三(4-氯苯基)膦

Database IDs

• CAS Number: 1159-54-2
• EC Number: 214-596-7
• MDL Number: MFCD00013639
• Beilstein Number: 751458
• PubChem SID: 24854999; 162070112
• PubChem CID: 70874

CALCULATED PROPERTIES

• Log P: 6.6606
• Molar Refractivity: 96.0373 cm^3
• Polarizability: 37.80137 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.6606
• LogD (pH = 7.4): 6.6606

PROPERTIES

Physical Property

• Melting Point: 100-103 °C(lit.); 102-103°C; -97°C

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-37; 26-37/39; S:20-25-26-37/39
• 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: 95%; 97%
• Linear Formula: (ClC6H4)3P

DETAILS

MP Biomedicals - 05220322

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 249491

Packaging
1 g in glass bottle
Application
Catalyst for:
• Preparation of chromans and (E,E)-1,3-dienes via reaction of γ-substituted allenoates with aldehydes1
• Solvent-free Heck reactions2Cocatalyst in:
• Regioselective carbomagnesiation of terminal alkynes and enynes with alkyl Grignard reagents3
• Rhodium-catalyzed coordination-assisted regioselective alkenylation of aromatic C-H bonds with terminal silylacetylenes4
• Rhodium-catalyzed hydrogenation reactions5
• Platinum-catalyzed allylation reactions6

REFERENCES

• In a study of the Mitsunobu coupling of phosphonic acids with alcohols in the presence of Diisopropyl azodicarboxylate, L10386 to give phosphonate esters, reaction times were greatly reduced by the use of this phosphine in place of the usual triphenylphosphine: J. Org. Chem., 59, 658 (1994).