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497940

Sigma-Aldrich

3-Cyanophenylzinc iodide solution

0.5 M in THF

Linear Formula:
NCC6H4ZnI
CAS Number:
Molecular Weight:
294.41
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

concentration

0.5 M in THF

density

0.998 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

I[Zn]c1cccc(c1)C#N

InChI

1S/C7H4N.HI.Zn/c8-6-7-4-2-1-3-5-7;;/h1-2,4-5H;1H;/q;;+1/p-1

InChI key

MWVOJRQBIBGPBW-UHFFFAOYSA-M

Related Categories

Application

3-Cyanophenylzinc iodide can be used:
  • As a reagent/substrate in the palladium-catalyzed synthesis of 5-substituted 2-furaldehydes of biological importance.
  • As a substrate in the di-functionalization of indenes via α-carbonylalkylarylation to yield α-carbonyl- alkylarylated indenes.

Packaging

50 mL in Sure/Seal™

Legal Information

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK Germany

WGK 3

Flash Point(F)

1.0 °F - closed cup

Flash Point(C)

-17.22 °C - closed cup

Certificate of Analysis

Certificate of Origin

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ, γ-Diarylcarbonyl and Aryltetralone Derivatives
Shekhar KC, et al.
Angewandte Chemie (International ed. in English), 132(21), 8124-8128 (2020)
Seung-Hoi Kim et al.
The Journal of organic chemistry, 78(5), 1984-1993 (2012-10-19)
Facile synthetic routes for the preparation of a wide range of 5-substituted 2-furaldehydes have been revealed. They were accomplished through either Pd-catalyzed cross-coupling reaction of various aryl- and heteroarylzinc halides with 5-bromo-2-furaldehyde or utilization of a new organozinc reagent, 5-(1,3-dioxolan-2-yl)-2-furanylzinc...
A convenient synthesis of 5-aryl-and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
Kim S and Rieke RD
Tetrahedron Letters, 51(19), 2657-2659 (2010)

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