Skip to Content
Merck
CN

939609

Sigma-Aldrich

[SIPr-H]2Pd2Cl6

greener alternative

powder or crystals

Synonym(s):

Bis-(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium)-hexachloropalladate

Sign Into View Organizational & Contract Pricing

About This Item

Empirical Formula (Hill Notation):
C54H78Cl6N4Pd2
CAS Number:
1802596-02-6
Molecular Weight:
1208.78
NACRES:
NA.21

Key Documents

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

Product Name

[SIPr-H]2Pd2Cl6,

form

powder or crystals

Quality Level

100

reaction suitability

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

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

color

brown to orange

greener alternative category

Aligned

SMILES string

CC(C(C=CC=C1C(C)C)=C1N2CC[N+](C3=C(C=CC=C3C(C)C)C(C)C)=C2)C.Cl[Pd]4(Cl)[ClH][Pd](Cl)(Cl)[ClH]4.CC(C(C=CC=C5C(C)C)=C5N6CC[N+](C7=C(C=CC=C7C(C)C)C(C)C)=C6)C

InChI

InChI=1S/2C27H39N2.4ClH.2Cl.2Pd/c2*1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;;;;;;;;/h2*9-14,17-21H,15-16H2,1-8H3;4*1H;;;;/q2*+1;;;;;;;2*+2/p-4

InChI key

WHCUDDZJJCQTRX-UHFFFAOYSA-J

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
[SIPr-H]2Pd2Cl6 is an ionic tetrachloropalladate complex containing 2 equivalents of the cationic imadazolium ligand 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium.

Application

Upon treatmeant with a suitable base, a catalytically active Pd-NHC complex can be generated in-situ. Suitable for use in difficult Suzuki-Miyaura and Buchwald-Hartwig cross-couplings reactions of aryl chlorides, and trans-amidation cross-coupling reactions of esters and amides.

Features and Benefits

[SPr-H]2Pd2Cl6 offers similar or greater performance to other similar Pd-NHC precatalysts available while offering several major advatages:
  • The precatalyst avoids the use of ′throw away′ stabilizing ligands often used in similar Pd-NHC complexes.
  • The more sustainable synthesis of [SIPr-H]2Pd2Cl6 compared to similar Pd-NHC complexes makes the product a more sustainable choice.
  • A competitive price, with a higher Pd percentage than many other Pd-NHC catalysts.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H319,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

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
MKCW5787

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.

Search for a COA

Already Own This Product?

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

Visit the Document Library

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