497924
6-Cyanohexylzinc bromide solution
0.5 M in THF
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About This Item
Linear Formula:
NC(CH2)6ZnBr
CAS Number:
Molecular Weight:
255.47
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
InChI
1S/C7H12N.BrH.Zn/c1-2-3-4-5-6-7-8;;/h1-6H2;1H;/q;;+1/p-1
SMILES string
Br[Zn]CCCCCCC#N
InChI key
YDXOVAJDARDUOR-UHFFFAOYSA-M
concentration
0.5 M in THF
density
0.944 g/mL at 25 °C
storage temp.
2-8°C
Application
6-Cyanohexylzinc 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 synthesize:
It can also be used as a reactant to synthesize:
- Cyanohexyl substituted aryl derivatives by palladium catalyzed coupling reaction with aryl bromides.
- Methyl 5-(6-cyanohexyl)-3-methylfuran-2-carboxylate, a key intermediate which is used in the preparation of cyclic furfuryl ether via Wittig rearrangement.
Legal Information
Product of Rieke® Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.
signalword
Danger
hcodes
Hazard Classifications
Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Central nervous system, Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
Regulatory Information
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Stereoselective construction of a β-isopropenyl alcohol moiety at the C (2) and (3) of kallolide A and pinnatin A using a [2, 3] Wittig rearrangement of cyclic furfuryl ethers
Tsubuki M, et al.
The Journal of Organic Chemistry, 68(26), 10183-10186 (2003)
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)
Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
Cao Q, et al.
Angewandte Chemie (International Edition in English), 130(35), 11509-11513 (2018)
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