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Thermo Scientific Chemicals
(Phenylthio)acetonitrile, 98%
CAS: 5219-61-4 | C8H7NS | 149.21 g/mol
化学物質識別子
CAS5219-61-4
仕様
スペックシート
スペックシートAppearance (Color)Clear colorless to pale yellow
Assay (GC)≥97.5%
FormLiquid
Refractive Index1.5795-1.5835 @ 20°C
Applications include, electron-deficient aromatics undergo vicarious nucleophilic substitution (VNS) reactions with the anion. Thus the molecule is equivalent to an acetonitrile anion synthon with thiophenate as the leaving group. For example, in the presence of solid NaOH in DMSO, nitrobenzene gives predominantly 4-nitrophenylacetonitrile, along with some of the 2-isomer.
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
Applications include, electron-deficient aromatics undergo vicarious nucleophilic substitution (VNS) reactions with the anion. Thus the molecule is equivalent to an acetonitrile anion synthon with thiophenate as the leaving group. For example, in the presence of solid NaOH in DMSO, nitrobenzene gives predominantly 4-nitrophenylacetonitrile, along with some of the 2-isomer.
Solubility
Not miscible or difficult to mix in water.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
Applications include, electron-deficient aromatics undergo vicarious nucleophilic substitution (VNS) reactions with the anion. Thus the molecule is equivalent to an acetonitrile anion synthon with thiophenate as the leaving group. For example, in the presence of solid NaOH in DMSO, nitrobenzene gives predominantly 4-nitrophenylacetonitrile, along with some of the 2-isomer.
Solubility
Not miscible or difficult to mix in water.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
RUO – Research Use Only
General References:
- Shuji Kanemasa, et al. Generation of Sulfur-Functionalized Nitrile Oxide, (Phenylthio)acetonitrile Oxide, and Synthetic Applications.Bulletin of the Chemical Society of Japan.,1988,61(11), 3973-3982.
- V. Suryanarayanan, et al. Selective electrofluorination of phenylacetonitrile and α-(phenylthio) acetonitrile — The role of sulfur and other operating parameters.Journal of Fluorine Chemistry.,1998,91(2), 153-157.
- Electron-deficient aromatics undergo vicarious nucleophilic substitution (VNS) reactions with the anion. Thus the molecule is equivalent to an acetonitrile anion synthon with thiophenate as the leaving group. For example, in the presence of solid NaOH in DMSO, nitrobenzene gives predominantly 4-nitrophenylacetonitrile, along with some of the 2-isomer: J. Org. Chem., 45, 1534 (1980).
- Electrochemical ɑ-monofluorination with Triethyl amine trihydrofluoride, L14417 occurs in good yield: J. Org. Chem., 60, 3459 (1995).