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A12869 (Phenylthio)acetonitrile, 98%

CAS Number
5219-61-4
Synonyms
Cyanomethyl phenyl sulfide
Phenylmercaptoacetonitrile

Stock No. Size Price ($) Quantity Availability
A12869-06 5g 50.20
A12869-14 25g 180.00
A12869-22 100g 639.00
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(Phenylthio)acetonitrile, 98%

MDL
MFCD00019831
EINECS
226-013-3

Chemical Properties

Formula
C6H5SCH2CN
Formula Weight
149.22
Boiling Point
146-147°/14mm
Flash Point
>110°(230°F)
Density
1.142
Refractive Index
1.5820
Storage & Sensitivity
Ambient temperatures.
Solubility
Not miscible or difficult to mix in water.

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.

Notes

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

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

GHS Hazard and Precautionary Statements

Hazard Statements: H302+H312+H332

Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled.

Precautionary Statements: P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P312-P330-P363-P501c

Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Rinse mouth. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
2042078
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2930.90
TSCA
No
RTECS
AM1900000

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