Skip to Content
MilliporeSigma

756482

Sigma-Aldrich

P(t-Bu)3 Pd G2

solid

Synonym(s):

Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II)

Slide 1 of 6
Sign Into View Organizational & Contract Pricing

Select a Size

250 MG
$78.62
500 MG
$109.50
2 G
$387.75
5 G
$738.65

$78.62

List Price$92.50Save 15%
Web-Only Promotion

Available to ship TODAYDetails


Request a Bulk Order

About This Item

Empirical Formula (Hill Notation):
C24H37ClNPPd
CAS Number:
Molecular Weight:
512.40
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Skip To


Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

P(t-Bu)3 Pd G2,

form

solid

Quality Level

feature

generation 2

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

167-170 °C (decomposition)

functional group

phosphine

SMILES string

NC1=C(C2=CC=CC=C2[Pd]Cl)C=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C

InChI

1S/C12H10N.C12H27P.ClH.Pd/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-10(2,3)13(11(4,5)6)12(7,8)9;;/h1-6,8-9H,13H2;1-9H3;1H;/q;;;+1/p-1

InChI key

ZVSLIOFJVMRWHJ-UHFFFAOYSA-M

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
804975753009792357
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: Cross Couplings, 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 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

-

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

167-170 °C (decomposition)

mp

87-150 °C (decomposition)

mp

218 °C (dec.)

mp

245-250 °C

feature

generation 2

feature

generation 3

feature

generation 2

feature

generation 3

General description

P(t-Bu)3 Pd G2 (Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II)) is a second generation (G2) precatalyst containing a biphenyl-based ligand. Product participates in various palladium catalyzed cross-coupling reactions, C-C, C-N and C-O bond formation reactions, and Suzuki-Miyaura coupling reactions. It generates active Pd catalyst at room temperature in the presence of weak phosphate or carbonate bases. It has been proposed as an active catalyst for use in Stille reactions of aryl halides (bromides and chlorides).[1]

Application

P(t-Bu)3 Pd G2 (Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II), Pd/P(t-Bu)3) may be used as catalyst in the following studies:
  • Synthesis of sterically hindered biaryls (tetra-ortho-substituted), via cross-coupling reactions of aryl chlorides.[1]
  • Stille cross-couplings reactions of aryl chloride.[2]
  • Synthesis of chloropeptin I, via Stille cross-coupling reaction.[2]
  • Heck reaction.[2]
  • Negishi cross-coupling reactions.[2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Adam F Littke et al.
Journal of the American Chemical Society, 124(22), 6343-6348 (2002-05-30)
Pd/P(t-Bu)(3) serves as an unusually reactive catalyst for Stille reactions of aryl chlorides and bromides, providing solutions to a number of long-standing challenges. An unprecedented array of aryl chlorides can be cross-coupled with a range of organotin reagents, including SnBu(4).
Gregory C Fu
Accounts of chemical research, 41(11), 1555-1564 (2008-10-25)
Metal-catalyzed coupling reactions of aryl electrophiles with organometallics and with olefins serve as unusually effective tools for forming new carbon-carbon bonds. By 1998, researchers had developed catalysts that achieved reactions of aryl iodides, bromides, and triflates. Nevertheless, many noteworthy challenges

Articles

Buchwald precatalysts and ligands are bulky electron-rich dialkylbiaryl phospine-based catalysts and structurally related ligands that improve reactivity in Pd-catalyzed cross - coupling reactions

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

Related Content

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service