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677728

Sigma-Aldrich

Bromo(tri-tert-butylphosphine)palladium(I) dimer

Synonym(s):

Dibromobis(tri-tert-butylphosphine)dipalladium, Dibromobis(tri-tert-butylphosphino)dipalladium(I), Palladium(I) tri-tert-butylphosphine bromide, dimer, Pd-113, [Pd(μ-Br)t-Bu3P]2

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About This Item

Linear Formula:
[Pd(C4H9)3PBr]2
CAS Number:
185812-86-6
Molecular Weight:
777.28
MDL number:
MFCD04114019
UNSPSC Code:
12352300
PubChem Substance ID:
24885391

storage temp.

−20°C

SMILES string

Br[Pd].Br[Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C

Application

  • Catalyst for γ-arylation of α,β-unsaturated esters from silyl ketene acetals (eq. 1)
  • Catalyst for carbon -sulfur bond formation (eq. 2)
  • Catalyst for diastereoselective arylation of 4-substituted cyclohexyl esters (eq. 3)
  • Catalyst for Suzuki coupling of hindered aryl bromides (eq. 4)
  • Catalyst for Buchwald-Hartwig amination reaction of aryl halides (eq. 5)
  • Catalyst for Negishi coupling reaction (eq. 6)
Catalyst for C-C, C-N, and N-S bond formation.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H250,H261,H314

Hazard Classifications

Pyr. Sol. 1 - Skin Corr. 1B - Water-react 2

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
50796JM
39996HM
04396DM
46496PK
67196DK

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Eric A Bercot et al.
Organic letters, 10(22), 5251-5254 (2008-10-29)
A diastereoselective palladium-catalyzed arylation of 4-substituted cyclohexyl esters has been developed. The reaction proceeds at room temperature in the presence of [(t-Bu3P)PdBr]2 providing products in up to 37:1 dr.
Chad C Eichman et al.
The Journal of organic chemistry, 74(10), 4005-4008 (2009-04-07)
A catalytic amount of zinc chloride in combination with a palladium catalyst ligated by a monodentate phosphine allows the coupling of aryl and alkyl thiols with aryl bromides in high yields. The addition of zinc chloride to a palladium catalyst
Palladium-catalyzed gamma-arylation of alpha,beta-unsaturated esters from silyl ketene acetals.
David S Huang et al.
Angewandte Chemie (International ed. in English), 49(33), 5757-5761 (2010-07-08)
Unparalleled rates for the activation of aryl chlorides and bromides: coupling with amines and boronic acids in minutes at room temperature.
James P Stambuli et al.
Angewandte Chemie (International ed. in English), 41(24), 4746-4748 (2002-12-14)
Takuo Hama et al.
Journal of the American Chemical Society, 128(15), 4976-4985 (2006-04-13)
The intermolecular alpha-arylation and vinylation of amides by palladium-catalyzed coupling of aryl bromides and vinyl bromides with zinc enolates of amides is reported. Reactions of three different types of zinc enolates have been developed. The reactions of aryl halides occur

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