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Safety Information

708739

Sigma-Aldrich

tBuXPhos Pd G1

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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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

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

708739-BULK:
708739-250MG:4548173924083
708739-1G:4548173924076
708739-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9466
SHBP2838
SHBH1164V
SHBG7999V
SHBF3053V

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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
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
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
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

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