520322
2-Cyanobenzylzinc bromide solution
0.5 M in THF
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About This Item
Linear Formula:
NCC6H4CH2ZnBr
CAS Number:
Molecular Weight:
261.43
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
concentration
0.5 M in THF
density
0.993 g/mL at 25 °C
functional group
nitrile
storage temp.
2-8°C
SMILES string
Br[Zn]Cc1ccccc1C#N
InChI
1S/C8H6N.BrH.Zn/c1-7-4-2-3-5-8(7)6-9;;/h2-5H,1H2;1H;/q;;+1/p-1
InChI key
LQRNYQAXNZETFP-UHFFFAOYSA-M
Application
2-Cyanobenzylzinc bromide can be used as a reactant:
- In the metal-catalyzed Negishi cross-coupling reactions to prepare aryl or heteroaryl derivatives via carbon-carbon bond formation.
- To synthesize 4-(2-Cyanobenzyl)-3′-(trifluoromethyl)biphenyl by reacting with aryl nonaflate in the presence of Pd(dba)2 as a catalyst.
- To prepare 2-[(2-cyanophenyl)methyl] benzamide by treating with 2-iodobenzamide using a nickel catalyst.
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
Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
Target Organs
Central nervous system, Respiratory system
Supplementary Hazards
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
1.4 °F - closed cup
Flash Point(C)
-17 °C - closed cup
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Improved nickel-catalyzed cross-coupling reaction conditions between ortho-substituted aryl iodides/nonaflates and alkylzinc iodides in solution and in the solid-phase
Jensen AE, et al.
Tetrahedron, 56(25), 4197-4201 (2000)
Visible-Light-Induced Nickel-Catalyzed Negishi Cross-Couplings by Exogenous-Photosensitizer-Free Photocatalysis
Abdiaj I, et al.
Angewandte Chemie (International Edition in English), 57(28), 8473-8477 (2018)
Palladium-catalyzed cross-coupling reactions with aryl nonaflates: a practical alternative to aryl triflates
Rottlander M and Knochel P
The Journal of Organic Chemistry, 63(1), 203-208 (1998)
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