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Sodium thiocyanate

Sodium sulfocyanate Sodium rhodanate Thiocyanic acid, sodium salt 225 g/100 mL (100 °C) | NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 | NFPA-S = Potassium thiocyanate Ammonium thiocyanate Sodium cyanide

Sodium thiocyanate (sometimes called sodium sulphocyanide) is the chemical compound with the formula NaSCN. This colorless deliquescent salt is one of the main sources of the thiocyanate anion. As such, it is used as a precursor for the synthesis of pharmaceuticals and other specialty chemicals. Thiocyanate salts are typically prepared by the reaction of cyanide with elemental sulfur:

:8 NaCN + S8 → 8 NaSCN

Sodium thiocyanate crystallizes in an orthorhombic cell. Each Na+ center is surrounded by three sulfur and three nitrogen ligands provided by the triatomic thiocyanate anion. It is commonly used in the laboratory as a test for the presence of Fe3+ ions.

Applications in chemical synthesis

Sodium thiocyanate is employed to convert alkyl halides into the corresponding alkylthiocyanates. Treatment of isopropyl bromide with sodium thiocyanate in a hot ethanolic solution affords isopropyl thiocyanate. Protonation of sodium thiocyanate affords isothiocyanic acid, S=C=NH (pKa = −1.28). Isothiocyanic acid, typically generated in situ from sodium thiocyanate, adds to anilines to afford 2-aminobenzothiazoles.

References

References

  1. [http://chemicalland21.com/industrialchem/organic/SODIUM%20THIOCYANATE.htm Sodium thiocyanate], chemicalland21.com
  2. Schwan, A. L.. (2001). "[[Encyclopedia of Reagents for Organic Synthesis]]". John Wiley & Sons.
  3. (1975). "Sodium thiocyanate". [[Acta Crystallographica]].
  4. R. L. Shriner. (1931). "Isopropyl Thiocyanate". Organic Syntheses.
  5. (2000). "Determination of the Acidity Constant of Isothiocyanic Acid in Aqueous Solution". [[Canadian Journal of Chemistry]].
  6. Allen, C. F. H.; VanAllan, J.. (1942). "2-Amino-6-Methylbenzothiazole".
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sodium-compounds thiocyanates
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