4-[5-(di-tert-butylphosphanyl)-1H-pyrazol-1-yl]-1,3,5-triphenyl-1H-pyrazole

• ChemBase ID: 140359
• Molecular Formular: C32H35N4P
• Molecular Mass: 506.620861
• Monoisotopic Mass: 506.25993377
• SMILES: CC(C)(C)P(c1ccnn1c1c(nn(c1c1ccccc1)c1ccccc1)c1ccccc1)C(C)(C)C
• Canonical SMILES: CC(P(C(C)(C)C)c1ccnn1c1c(nn(c1c1ccccc1)c1ccccc1)c1ccccc1)(C)C
• InChI: InChI=1S/C32H35N4P/c1-31(2,3)37(32(4,5)6)27-22-23-33-36(27)30-28(24-16-10-7-11-17-24)34-35(26-20-14-9-15-21-26)29(30)25-18-12-8-13-19-25/h7-23H,1-6H3
• InChIKey: PTXJGGGNGMPMBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[5-(di-tert-butylphosphanyl)-1H-pyrazol-1-yl]-1,3,5-triphenyl-1H-pyrazole
• IUPAC Traditional name: 4-[5-(di-tert-butylphosphanyl)pyrazol-1-yl]-1,3,5-triphenylpyrazole
• Synonyms: BippyPhos; 5-(Di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; 5-二叔丁基膦-1′,3′,5′-三苯基-1′H-[1,4′]二吡唑

Database IDs

• CAS Number: 894086-00-1
• MDL Number: MFCD09038440
• PubChem SID: 162234603; 24884860
• PubChem CID: 11547931

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.7966137
• LogD (pH = 7.4): 6.7967978
• Log P: 6.7968
• Molar Refractivity: 155.4335 cm^3
• Polarizability: 64.11499 Å^3
• Polar Surface Area: 35.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 169-173 °C
• Ligand For: Amidations; Buchwald-Hartwig Cross Coupling Reaction; Coupling Reactions

Safety Information

• German water hazard class: 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C32H35N4P

DETAILS

Sigma Aldrich - 676632

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Non-proprietary ligand for palladium-catalyzed amination of aryl halides including aryl chlorides. Works best when the palladium source is Pd2(dba)3 (328774).1