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498041

Sigma-Aldrich

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:
171860-68-7
Molecular Weight:
214.42
MDL number:
MFCD00671991
UNSPSC Code:
12352103
PubChem Substance ID:
24873166
NACRES:
NA.22

Quality Level

100

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

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.
  • Negishi cross-coupling reactions with various haloarenes in presence of Pd-complex catalyst.
  • 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.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

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Danger

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

supp_hazards

EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS0736
SHBQ3683
SHBM5002
SHBL5572
SHBJ9411

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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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