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676632

Sigma-Aldrich

5-(Di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole

97%

Synonym(s):

BippyPhos

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About This Item

Empirical Formula (Hill Notation):
C32H35N4P
CAS Number:
894086-00-1
Molecular Weight:
506.62
MDL number:
MFCD09038440
UNSPSC Code:
12352005
PubChem Substance ID:
24884860
NACRES:
NA.22

assay

97%

form

solid

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Amidations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Coupling Reactions

mp

169-173 °C

functional group

phosphine

SMILES string

CC(C)(C)P(c1ccnn1-c2c(nn(-c3ccccc3)c2-c4ccccc4)-c5ccccc5)C(C)(C)C

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

InChI key

PTXJGGGNGMPMBG-UHFFFAOYSA-N

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).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Brian J Kotecki et al.
Organic letters, 11(4), 947-950 (2009-01-31)
A general and practical method for the preparation of unsymmetrically substituted ureas has been developed utilizing palladium-catalyzed amidation. Both aryl bromides and chlorides, as well as heteroaryl chlorides, have been coupled to aryl, benzyl, and aliphatic ureas by using a
Achim Porzelle et al.
Organic letters, 11(1), 233-236 (2008-11-28)
The bis-pyrazole phosphine ligand BippyPhos is effective for the palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides, chlorides, and iodides. Reactions proceed smoothly at 80 degrees C in toluene in the presence of Cs(2)CO(3) to give synthetically versatile N-arylhydroxylamine products in
Tetrahedron Letters, 47, 3727-3727 (2006)
Saravanan Gowrisankar et al.
Journal of the American Chemical Society, 132(33), 11592-11598 (2010-08-03)
An efficient procedure for palladium-catalyzed coupling reactions of (hetero)aryl bromides and chlorides with primary aliphatic alcohols has been developed. Key to the success is the synthesis and exploitation of the novel bulky di-1-adamantyl-substituted bipyrazolylphosphine ligand L6. Reaction of aryl halides

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