498041
Cyclopentylzinc bromide solution
0.5 M in THF
Synonym(s):
Bromo(cyclopentyl)zinc, Bromocyclopentylzinc
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About This Item
Linear Formula:
C5H9ZnBr
CAS Number:
Molecular Weight:
214.42
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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concentration
0.5 M in THF
density
0.955 g/mL at 25 °C
storage temp.
2-8°C
SMILES string
Br[Zn]C1CCCC1
InChI
1S/C5H9.BrH.Zn/c1-2-4-5-3-1;;/h1H,2-5H2;1H;/q;;+1/p-1
InChI key
GOPYCBPMCCJYSN-UHFFFAOYSA-M
Related Categories
Application
Cyclopentylzinc bromide is an organozinc reagent that can be used in:
- The synthesis of polyfunctional indoles by reacting with various aryldiazonium salts via Fischer indole synthesis.[1]
- Negishi cross-coupling reactions with various haloarenes in presence of Pd-complex catalyst.[2]
- The preparation of aryl alkyl ketones by alkylation of aryl N-methyl-N-tosyl or N-benzyl-N-(tert-butoxycarbonyl) amide derivatives in the presence of Ni catalyst and imidazolidinylidene ligand.[3]
Legal Information
Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3 - Water-react 2
Target Organs
Respiratory system
Supplementary Hazards
Storage Class Code
4.3 - Hazardous materials which set free flammable gases upon contact with water
WGK
WGK 3
Flash Point(F)
1.4 °F - closed cup
Flash Point(C)
-17 °C - closed cup
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Nickel-catalyzed alkylation of amide derivatives
Simmons BJ, et al.
ACS Catalysis, 6(5), 3176-3179 (2016)
Efficient preparation of polyfunctional indoles via a zinc organometallic variation of the Fischer indole synthesis
Zhang Z-G, et al.
Synthesis, 2011(01), 23-29 (2011)
Mild Negishi cross-coupling reactions catalyzed by acenaphthoimidazolylidene palladium complexes at low catalyst loadings
Liu Z, et al.
The Journal of Organic Chemistry, 78(15), 7436-7444 (2013)
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