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275891

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
NACRES:
NA.22
PubChem Substance ID:
24856679
UNSPSC Code:
12352202
EC Number:
235-161-8
MDL number:
MFCD00012412
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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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ5981
MKCX7753
MKCW4971
MKCV6969
MKCV6726

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Palladium-catalysed direct synthesis of benzo [b] thiophenes from thioenols.
Inamoto K, et al.
Chemical Communications (Cambridge, England), 43, 5529-5531 (2008)
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)
Dichloro(1,5?cyclooctadiene)palladium(II).
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2009)
View All Related Papers

Global Trade Item Number

SKUGTIN
275891-2G04061826177679