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900275

Sigma-Aldrich

(t-Bu)PhCPhos

95%, powder or crystals

Synonym(s):

2-[(tert-Butyl)phenylphosphino]-2′,6′-bis(N,N-dimethylamino)biphenyl

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About This Item

Empirical Formula (Hill Notation):
C26H33N2P
CAS Number:
1660153-91-2
Molecular Weight:
404.53
MDL number:
MFCD29905429
UNSPSC Code:
12352200
NACRES:
NA.22

Key Documents

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Product Name

(t-Bu)PhCPhos, 95%

Quality Level

100

assay

95%

form

powder or crystals

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings
reagent type: ligand

mp

112 °C

functional group

phosphine

SMILES string

P(C(C)(C)C)(c2c(cccc2)c3c(cccc3N(C)C)N(C)C)c1ccccc1

InChI

1S/C26H33N2P/c1-26(2,3)29(20-14-9-8-10-15-20)24-19-12-11-16-21(24)25-22(27(4)5)17-13-18-23(25)28(6)7/h8-19H,1-7H3

InChI key

HTHOMNNVAUPLKK-UHFFFAOYSA-N

Related Categories

Application

(t-Bu)PhCPhos is the Pd G3 complex, from the Buchwald group offers best-in-class performance in the arylation of sterically hindered primary amines.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Paula Ruiz-Castillo et al.
Journal of the American Chemical Society, 137(8), 3085-3092 (2015-02-05)
We report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic analysis and rational design have led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The process was effective in

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