497894
4-Cyanobutylzinc bromide solution
0.5 M in THF
Synonym(s):
Bromo(4-cyanobutyl)zinc
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About This Item
Linear Formula:
NC(CH2)4ZnBr
CAS Number:
Molecular Weight:
227.42
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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concentration
0.5 M in THF
density
0.971 g/mL at 25 °C
functional group
nitrile
storage temp.
2-8°C
SMILES string
Br[Zn]CCCCC#N
InChI
1S/C5H8N.BrH.Zn/c1-2-3-4-5-6;;/h1-4H2;1H;/q;;+1/p-1
InChI key
HJYQQTDSYHJSLL-UHFFFAOYSA-M
Related Categories
Application
4-Cyanobutylzinc bromide is an organozinc compound, which can be used as a reactant in palladium-catalyzed Negishi cross-coupling reaction to construct carbon-carbon bonds by coupling with organic halides or triflates.
It can also be used as a reactant to prepare:
It can also be used as a reactant to prepare:
- 5-(3-Thienyl)pentanenitrile by reacting with 3-bromothiophene in the presence of a nickel catalyst.
- α-Cyanobutyl vinylphosphonates by palladium-catalyzed Negishi coupling vinylation reaction with α-(pseudo)halo vinylphosphonates.
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
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Supplementary Hazards
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
-6.2 °F - (THF)
Flash Point(C)
-21.2 °C - (THF)
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An efficient method for the synthesis of 3-alkylthiophenes bearing functional groups on the side chain: imides and amides
D Jian, et al.
Synthetic Metals, 139(1), 81-88 (2003)
Palladium-catalysed coupling of α-halo vinylphosphonate and α-phosphonovinyl sulfonate with alkylzincs: straightforward and versatile synthesis of ?-alkyl vinylphosphonates
Zhang Li, et al.
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 5(9), 1457-1461 (2018)
Room-temperature Negishi cross-coupling of unactivated alkyl bromides with alkyl organozinc reagents utilizing a Pd/N-heterocyclic carbene catalyst
Hadei N, et al.
The Journal of Organic Chemistry, 70(21), 8503-8507 (2005)
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