bromo({[2-(hydroxymethyl)phenyl]methyl})palladium; triphenylphosphane

• ChemBase ID: 140060
• Molecular Formular: C26H24BrOPPd
• Molecular Mass: 569.765921
• Monoisotopic Mass: 567.97830002
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(c(c1)CO)C[Pd]Br
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.Br[Pd]Cc1ccccc1CO
• InChI: InChI=1S/C18H15P.C8H9O.BrH.Pd/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-7-4-2-3-5-8(7)6-9;;/h1-15H;2-5,9H,1,6H2;1H;/q;;;+1/p-1
• InChIKey: ADEHOQBJPPXQEY-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: bromo({[2-(hydroxymethyl)phenyl]methyl})palladium; triphenylphosphane
• IUPAC Traditional name: bromo({[2-(hydroxymethyl)phenyl]methyl})palladium; triphenylphosphine
• Synonyms: Bromo[(2-(hydroxy-κO)methyl)phenylmethyl-κC](triphenylphosphine)palladium (II); 溴[(2-(羟基-κO)甲基)苯基甲基-κC](三苯基膦)钯(II)

Database IDs

• CAS Number: 849417-33-0
• MDL Number: MFCD08276875
• PubChem SID: 24884791; 162234304
• PubChem CID: 11592232

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• Molar Refractivity: 81.6229 cm^3
• Polarizability: 32.34495 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 165-170 °C

Safety Information

• German water hazard class: 3

Product Information

• Impurities: ≤20 mol % Dibromo[μ-[1,2-phenylenebis(methylene)]]tetrakis(triphenylphosphine)palladium dimer
• Linear Formula: C8H9OPdBr · (C6H5)3P

DETAILS

Sigma Aldrich - 666327

Application
Catalyst for the low pressure carbonylation of aryl halides leading to phenylacetic acids in near quantitative yield.3
Catalyst for:
• Stille carbonylation of N-protected bromomethylindoles1
• Carbonylation of arylmethyl halides2
Packaging
1 g in glass bottle
250 mg in glass bottle