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Merck

708739

Sigma-Aldrich

tBuXPhos Pd G1

solid

Synonym(s):

t-BuXPhos palladium(II) phenethylamine chloride, tBuXPhos-Pd-G1, Chloro[2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II), [2-(Di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II) chloride, t-BuXPhos Palladacycle, t-BuXPhos precatalyst

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250 MG
€58.42
1 G
€193.50

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About This Item

Empirical Formula (Hill Notation):
C37H55ClNPPd
CAS Number:
1142811-12-8
Molecular Weight:
686.69
MDL number:
MFCD12911909
UNSPSC Code:
12161600
PubChem Substance ID:
329762821
NACRES:
NA.22

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Product Name

tBuXPhos Pd G1,

form

solid

Quality Level

100

feature

generation 1

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

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704954707589776106
tBuXPhos Pd G1

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708739

tBuXPhos Pd G1

XPhos Pd G1

Sigma-Aldrich

704954

XPhos Pd G1

RuPhos Pd G1 Methyl t­-Butyl Ether Adduct 95%

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707589

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AdBrettPhos Pd G3

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776106

AdBrettPhos Pd G3

reaction suitability

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

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

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

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

form

solid

form

solid

form

solid

form

solid

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

150-159 °C

mp

205-210 °C

mp

180-200 °C

mp

251-253 °C

feature

generation 1

feature

generation 1

feature

generation 1

feature

generation 3

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst for C-C bond and C-N bond formation.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H351

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9466
SHBP2838
SHBH1164V
SHBG7999V
SHBF3053V

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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.
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
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.
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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