dicyclohexyl({2-[2,4,6-tris(propan-2-yl)phenyl]phenyl})phosphane

• ChemBase ID: 69859
• Molecular Formular: C33H49P
• Molecular Mass: 476.715921
• Monoisotopic Mass: 476.3571882
• SMILES: c1(c(cccc1)P(C1CCCCC1)C1CCCCC1)c1c(cc(cc1C(C)C)C(C)C)C(C)C
• Canonical SMILES: CC(c1cc(cc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)C(C)C)C(C)C)C
• InChI: InChI=1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3
• InChIKey: UGOMMVLRQDMAQQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dicyclohexyl({2-[2,4,6-tris(propan-2-yl)phenyl]phenyl})phosphane
• IUPAC Traditional name: xphos; dicyclohexyl[2-(2,4,6-triisopropylphenyl)phenyl]phosphane
• Synonyms: 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl; Dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine; XPhos; XPhos; 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl; 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl impregnated tablets; ChemDose™, X-Phos impregnated tablets; X-Phos, ChemDose™ tablets; 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl; 2-二环己基磷-2′,4′,6′-三异丙基联苯; 2-二环己基膦-2′,4′,6′-三异丙基联苯浸渍片; ChemDose™，X-Phos 浸渍片; X-Phos，ChemDose™ 片

Database IDs

• CAS Number: 564483-18-7
• MDL Number: MFCD04117682
• PubChem SID: 24885834; 162035584; 24882906
• PubChem CID: 11155794
• Chemspider ID: 9330902
• Wikipedia Title: XPhos

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 10.071707
• LogD (pH = 7.4): 10.197986
• Log P: 10.3948
• Molar Refractivity: 151.7063 cm^3
• Polarizability: 61.180626 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: organic solvents
• Apperance: colorless solid
• Melting Point: 187-190 °C; 187-190 °C(lit.)
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; C-C Bond Formation; Heck Reaction; Hiyama Coupling; Negishi Coupling; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• TSCA Listed: false
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351; H413
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%; 97%; 98%
• Matrix: Magnesium aluminometasilicate base material
• Empirical Formula (Hill Notation): C33H49P

DETAILS

Sigma Aldrich - 638064

Application
Ligand for increased scope of Pd-catalyzed amination and amidation via arene sulfonates, aryl halides.1
Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd. Synthesis of regioregular polythiophenes.
Packaging
1, 5, 25, 100 g in glass bottle
Legal Information
Usage subject to US Patents 6307087 and 6395916.

Sigma Aldrich - 685151

Frequently Asked Questions
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Legal Information
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