708739

Sigma-Aldrich

tBuXPhos Pd G1

Synonym(s):
tBuXPhos-Pd-G1, Chloro[2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II), t-BuXPhos Palladacycle, [2-(Di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II) chloride, t-BuXPhos precatalyst, t-BuXPhos palladium(II) phenethylamine chloride
Empirical Formula (Hill Notation):
C37H55ClNPPd
CAS Number:
Molecular Weight:
686.69
MDL number:
PubChem Substance ID:
NACRES:
NA.22

feature

generation 1

Quality Level

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings

mp

150-159 °C

functional group

phosphine

SMILES string

NCCc1ccccc1[Pd]Cl.CC(C)c2cc(C(C)C)c(c(c2)C(C)C)-c3ccccc3P(C(C)(C)C)C(C)(C)C

InChI

1S/C29H45P.C8H10N.ClH.Pd/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12;9-7-6-8-4-2-1-3-5-8;;/h13-21H,1-12H3;1-4H,6-7,9H2;1H;/q;;;+1/p-1

InChI key

LQRWNWRVOIDQOD-UHFFFAOYSA-M

Application

Catalyst for C-C bond and C-N bond formation.

Packaging

1 g in glass bottle
250 mg in glass bottle

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

hazcat

Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Brian K Lee et al.
Tetrahedron letters, 50(26), 3672-3674 (2009-07-01)
Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed...
Mark R Biscoe et al.
Organic letters, 11(8), 1773-1775 (2009-03-20)
Simple, efficient procedures for the monoarylation of acetate esters and aryl methyl ketones using aryl chlorides are presented. Previously, no general method was available to ensure the highly selective monoarylation of these classes of substrates using aryl chlorides. Using palladium...
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...
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon...
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses...

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