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

• ChemBase ID: 142749
• Molecular Formular: C41H59ClNPPd
• Molecular Mass: 738.760621
• Monoisotopic Mass: 737.3108512
• SMILES: CC(C)c1cc(c(c(c1)C(C)C)c1ccccc1P(C1CCCCC1)C1CCCCC1)C(C)C.c1ccc(c(c1)CCN)[Pd]Cl
• Canonical SMILES: CC(c1cc(cc(c1c1ccccc1P(C1CCCCC1)C1CCCCC1)C(C)C)C(C)C)C.NCCc1ccccc1[Pd]Cl
• InChI: InChI=1S/C33H49P.C8H10N.ClH.Pd/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;9-7-6-8-4-2-1-3-5-8;;/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3;1-4H,6-7,9H2;1H;/q;;;+1/p-1
• InChIKey: HTAJCNQBAFZEJO-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(2-aminoethyl)phenyl](chloro)palladium; dicyclohexyl({2-[2,4,6-tris(propan-2-yl)phenyl]phenyl})phosphane
• IUPAC Traditional name: [2-(2-aminoethyl)phenyl](chloro)palladium; xphos
• Synonyms: XPhos Palladacycle; XPhos precatalyst; (2-Dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl)]palladium(II) chloride; (XPhos) palladium(II) phenethylamine chloride; Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl)]palladium(II); (2-二环己基膦基-2′,4′,6′-三异丙基-1,1′-联苯基)[2-(2-氨乙基)苯基)]氯化钯(II); (XPhos) 钯(II)苯乙胺氯化物; 氯(2-二环己基膦基-2′,4′,6′-三异丙基-1,1′-联苯基)[2-(2-氨基乙基)苯基)]钯(II)

Database IDs

• CAS Number: 1028206-56-5
• MDL Number: MFCD13194128
• PubChem SID: 162236975
• PubChem CID: 24886384

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: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 205-210 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-52/53
• Safety Statements: 26-61
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H412
• GHS Precautionary statements: P261-P273-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C41H59ClNPPd

DETAILS

Sigma Aldrich - 704954

General description
Material may contain up to 5% pentane
Packaging
1 g in glass bottle
250 mg in glass bottle
Legal Information
Usage subject to US Patents 6307087 and 6395916.
Application
Application Guide for Palladium Catalyzed Cross-Coupling ReactionsCatalyst used for:
• Amination / cyclization reactions1
• C-N bond-forming reactions via packed-bed microreactors2
• Boration of aryl chlorides3
• Arylation of oxazole4
• Cross-coupling reactions5,6