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675938

Sigma-Aldrich

Me4tButylXphos

96%

Synonym(s):

2-Di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl, Tetramethyl di-tBuXPhos, Tetramethyl tBuXPhos

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About This Item

Empirical Formula (Hill Notation):
C33H53P
CAS Number:
857356-94-6
Molecular Weight:
480.75
MDL number:
MFCD09038436
UNSPSC Code:
12352002
PubChem Substance ID:
24885309
NACRES:
NA.22

Assay

96%

form

solid

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation

mp

168-172 °C

functional group

phosphine

SMILES string

CC1=C(C)C(C)=C(C)C(C(C(C(C)C)=CC(C(C)C)=C2)=C2C(C)C)=C1P(C(C)(C)C)C(C)(C)C

InChI

1S/C33H53P/c1-19(2)26-17-27(20(3)4)30(28(18-26)21(5)6)29-24(9)22(7)23(8)25(10)31(29)34(32(11,12)13)33(14,15)16/h17-21H,1-16H3

InChI key

RCRYEYMHBHPZQD-UHFFFAOYSA-N

Application

Learn more about Buchwald Phosphine Ligands

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Takashi Ikawa et al.
Journal of the American Chemical Society, 129(43), 13001-13007 (2007-10-09)
We present results on the amidation of aryl halides and sulfonates utilizing a monodentate biaryl phosphine-Pd catalyst. Our results are in accord with a previous report that suggests that the formation of kappa(2)-amidate complexes is deleterious to the effectiveness of
N Ian Rinehart et al.
Science (New York, N.Y.), 381(6661), 965-972 (2023-08-31)
Machine-learning methods have great potential to accelerate the identification of reaction conditions for chemical transformations. A tool that gives substrate-adaptive conditions for palladium (Pd)-catalyzed carbon-nitrogen (C-N) couplings is presented. The design and construction of this tool required the generation of
Huy Tran et al.
Angewandte Chemie (International ed. in English), 61(1), e202110575-e202110575 (2021-10-30)
A one-pot cascade sequence to generate synthetically challenging polycyclic scaffolds is reported utilizing a novel Lewis acid gold catalyst for the key cyclization step, enabling the divergent synthesis of both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores through both ligand and reaction condition
Kevin W Anderson et al.
Journal of the American Chemical Society, 128(33), 10694-10695 (2006-08-17)
The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd(2)dba(3) and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H(2)O. We have also
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand
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Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

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