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579157

Sigma-Aldrich

4-Iodobenzonitrile

97%

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About This Item

Linear Formula:
IC6H4CN
CAS Number:
3058-39-7
Molecular Weight:
229.02
MDL number:
MFCD00051310
UNSPSC Code:
12352100
PubChem Substance ID:
24880973
NACRES:
NA.22

Assay

97%

form

solid

mp

124-128 °C (lit.)

SMILES string

Ic1ccc(cc1)C#N

InChI

1S/C7H4IN/c8-7-3-1-6(5-9)2-4-7/h1-4H

InChI key

XOKDXPVXJWTSRM-UHFFFAOYSA-N

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Application

4-Iodobenzonitrile may be used in the synthesis of the following:
  • ethyl-4′-cyano-4-nitro[1,1′-biphenyl]-2-carboxylate via a multi-step reaction process
  • 2-(4-cyanophenyl)tellurophene obtained via Stille coupling with tellurophene
  • 2,5-bis(4-cyanophenyl)tellurophene obtained via Stille coupling with 2,5-bis(trimethylstannyl)tellurophene
  • ethyl-4′-cyano-6-{[(E)-phenylmethylidene]amino}[1,1′-biphenyl]-3-carboxylate via a multi-step reaction process

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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"Preparation and reactions of functionalized arylmagnesium reagents"
Jensen EA, et al.
Synthesis, 2002(04), 0565-0569 (2002)
"Synthesis of Nitro-Substituted Polyfunctional Biphenyls by Negishi Cross-Coupling of o-Nitroarylzinc Reagents"
Sapountzis I, et al.
Advanced Synthesis & Catalysis, 346(07), 709-712 (2004)
"Synthesis and stille cross-coupling reactions of 2-(tributylstannyl)-and 2, 5-bis (trimethylstannyl) tellurophene"
Sweat.PD and Stephens.EC
Synthesis, 2009(19), 3214-3218 (2009)
Nico Giordano et al.
Molecules (Basel, Switzerland), 24(10) (2019-05-30)
The crystal structure of 4-iodobenzonitrile, which is monoclinic (space group I2/a) under ambient conditions, contains chains of molecules linked through C≡N···I halogen-bonds. The chains interact through CH···I, CH···N and π-stacking contacts. The crystal structure remains in the same phase up

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