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275891

Sigma-Aldrich

Dichloro(1,5-cyclooctadiene)palladium(II)

99%

Synonym(s):

PdCl2(cod)

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About This Item

Empirical Formula (Hill Notation):
C8H12Cl2Pd
CAS Number:
12107-56-1
Molecular Weight:
285.51
EC Number:
235-161-8
MDL number:
MFCD00012412
UNSPSC Code:
12352202
PubChem Substance ID:
24856679
NACRES:
NA.22

Quality Level

100

Assay

99%

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

mp

210 °C (dec.) (lit.)

SMILES string

Cl[Pd]Cl.C1CC=CCCC=C1

InChI

1S/C8H12.2ClH.Pd/c1-2-4-6-8-7-5-3-1;;;/h1-2,7-8H,3-6H2;2*1H;/q;;;+2/p-2/b2-1-,8-7-;;;

InChI key

RRHPTXZOMDSKRS-PHFPKPIQSA-L

Related Categories

Application

Dichloro(1,5-cyclooctadiene)palladium(II) is a commonly used catalyst to protect alcohols as acetals by treating with 2-benzyloxy-1-propene; to synthesize bicyclooctanes from diethyl malonate and in alkene carbonylation. It can also be used to catalyze the Heck coupling of nonactivated vinyl phosphates with electron deficient alkenes; the synthesis of benzo[b]thiophenes from thioenols and to prepare an active catalyst for Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions.
Catalyst for C-C bond and C-N formation, used in Heck coupling of alkynes with alkenes , Suzuki cross-coupling of aryl bromides , allylic substitution of oximes with allylic acetate , and methoxycarbonylation of iodobenzene.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Studies on the Heck reaction with alkenyl phosphates: Can the 1, 2-migration be controlled? Scope and Limitations.
Ebran J P, et al.
Journal of the American Chemical Society, 129(21), 6931-6942 (2007)
Palladium-catalysed direct synthesis of benzo [b] thiophenes from thioenols.
Inamoto K, et al.
Chemical Communications (Cambridge, England), 43, 5529-5531 (2008)
Dichloro(1,5?cyclooctadiene)palladium(II).
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2009)
An inexpensive and highly stable ligand 1, 4-bis (2-hydroxy-3, 5-di-tert-butylbenzyl) piperazine for Mizoroki?Heck and room temperature Suzuki?Miyaura cross-coupling reactions.
Mohanty S, et al.
Tetrahedron, 64(1), 240-247 (2008)
Eda Rami Reddy et al.
Dalton transactions (Cambridge, England : 2003), 44(40), 17600-17616 (2015-09-24)
A series of five palladium(ii) pyridyl-imine Schiff base complexes 5a-e containing boronate esters with protected sugar diols derived from d-xylose, l-sorbose and d-mannitol were designed and synthesized starting from pyridyl-imines generated in situ from 3-aminophenyl boronate ester of sugars 3a-e
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