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Tetracyanoethylene, 98%, Thermo Scientific Chemicals
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Catalog number A13945.03
Price (USD)/ Each
27.65
Special Offer
Online exclusive
Ends: 31-Dec-2024
32.10 Save 4.45 (14%)
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Quantity:
1 g
Price (USD)/ Each
27.65
Special Offer
Online exclusive
Ends: 31-Dec-2024
32.10 Save 4.45 (14%)
Tetracyanoethylene, 98%, Thermo Scientific Chemicals
Catalog numberA13945.03
Price (USD)/ Each
27.65
Special Offer
Online exclusive
Ends: 31-Dec-2024
32.10 Save 4.45 (14%)
-
Chemical Identifiers
CAS670-54-2
IUPAC Nameeth-1-ene-1,1,2,2-tetracarbonitrile
Molecular FormulaC6N4
InChI KeyNLDYACGHTUPAQU-UHFFFAOYSA-N
SMILESN#CC(C#N)=C(C#N)C#N
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Specifications
Specification Sheet
Specification SheetMelting Point (clear melt)196.0-202.0?C (UK Sourced Material)
Appearance (Color)White to brown
Assay (GC)≥97.5%
FormCrystals or powder or crystalline powder or chunks
CommentMaterial Sourced in UK and US
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability. As reactant for Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives, Thermal addition reaction with alkynes, One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds, Synthesis of cobalt tetracyanoethylene films, Biotransformation by Botrytis cinerea.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability. As reactant for Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives, Thermal addition reaction with alkynes, One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds, Synthesis of cobalt tetracyanoethylene films, Biotransformation by Botrytis cinerea.
Solubility
Soluble in methanol, benzene, toluene, water (hydrolyses to form HCN), and ether (slightly).
Notes
Moisture Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability. As reactant for Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives, Thermal addition reaction with alkynes, One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds, Synthesis of cobalt tetracyanoethylene films, Biotransformation by Botrytis cinerea.
Solubility
Soluble in methanol, benzene, toluene, water (hydrolyses to form HCN), and ether (slightly).
Notes
Moisture Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.
RUO – Research Use Only
General References:
- Masakazu Morimoto,; Kimie Murata,; Tsuyoshi Michinobu. Photochemical control of a highly efficient addition reaction between electron-rich alkynes and tetracyanoethylene.. Chemical Communications. 2011 47 (35), 9819-9821.
- Songlin Niu,; Gilles Ulrich,; Pascal Retailleau,; Raymond Ziessel. Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes. Organic Letters, 2011, 13 (19), 4996-4999.
- Versatile reagent and reactive dienophile. Reviews: Miscellaneous chemistry: Chem. Rev., 67, 611 (1967); Synthesis, 249 (1986); Addition and cycloaddition reactions: Synthesis, 749 (1987); Organometallic chemistry: Synthesis, 959 (1987).
- π-Acid catalyst, compare DDQ (2,3-Dichloro-5,6-dicyanobenzoquinone, A11879) for the rearrangement of epoxides to ketones, formation of acetonides (1,3-dioxolanes) by reaction of epoxides with acetone: Chem. Lett., 17 (1993), formation of epoxides with hydrogen peroxide: Chem. Pharm. Bull., 43, 686 (1995), and for stereospecific alcoholysis of epoxides under mild conditions: Synlett, 847 (1993). In the presence of pyridine, carboxylic acids are converted to anhydrides: Tetrahedron Lett., 26, 1503 (1985). In an alcohol as solvent, catalyzes esterification and transesterification reactions: Chem. Lett., 55 (1997).
- Also catalyzes the carbon-carbon bond formation reactions of aldehydes, ketones and acetals with silylated nucleophiles including Trimethyl silyl cyanide, A19598, allyltrimethylsilane, silyl enol ethers and triethylsilane: J. Chem. Soc., Perkin 1, 2155 (1995).