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5219-61-4 - (Phenylthio)acetonitrile, 98% - Cyanomethyl phenyl sulfide - Phenylmercaptoacetonitrile - A12869 - Alfa Aesar

A12869 (Phenylthio)acetonitrile, 98%

CAS-Nummer
5219-61-4
Synonyme
Cyanomethyl phenyl sulfide
Phenylmercaptoacetonitrile

Größe Preis ($) Menge Verfügbarkeit
5g 56,65
25g 178,20
100g 566,40
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(Phenylthio)acetonitrile, 98%

MDL
MFCD00019831
EINECS
226-013-3

Chemische Eigenschaften

Formel
C6H5SCH2CN
Molmasse
149.22
Siedepunkt
146-147°/14mm
Flammpunkt
>110°(230°F)
Dichte
1.142
Brechungsindex
1.5820
Löslichkeit
Not miscible or difficult to mix in water.

Anwendungen

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.

Bemerkungen

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literaturverweise

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 Triethyl­amine trihydrofluoride, L14417 occurs in good yield: J. Org. Chem., 60, 3459 (1995).

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302

Harmful if swallowed.

Sicherheitshinweise: P280f

Wear protective clothing.

Weitere Referenzen

Beilstein
2042078
Harmonized Tariff Code
2930.90
TSCA
No
RTECS
AM1900000

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