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Sodium thiocyanate

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Sodium thiocyanate
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This page is a soft redirect. Names

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IUPAC name
Sodium thiocyanate
Other names
Sodium rhodanide
Sodium sulfocyanate
Sodium rhodanate
Thiocyanic acid, sodium salt
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540-72-7 7pxY ChEBI CHEBI:30952 7pxY ChEMBL ChEMBL1644028 7pxN
ChEMBL84336 7pxY
ChEMBL1078613 7pxY ChemSpider 10443 7pxY EC number 208-754-4 Jmol-3D images Image PubChem Template:Chembox PubChem/format RTECS number XL2275000 Template:Chembox UNII colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Properties

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NaSCN Molar mass 81.072 g/mol Appearance deliquescent colorless crystals Density 1.735 g/cm3 Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". decomposes 139 g/100 mL (21 °C)
225 g/100 mL (100 °C) Solubility soluble in acetone, alcohols, ammonia, SO2 Acidity (pKa) -1.28 1.545 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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Crystal structure orthorhombiv colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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SDS ICSC 0675 EU Index 615-004-00-3 EU classification Harmful (Xn) R-phrases R20/21/22, R32, R36, R37, R38 S-phrases S22, S26, S36 NFPA 704

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764 mg/kg (oral, rat)[1] colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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Other anions
Sodium cyanate
Sodium cyanide
Other cations
Potassium thiocyanate
Ammonium thiocyanate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN verify (what is10pxY/10pxN?) Infobox references

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.[2] 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.[3] 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. Closely related reagents include ammonium thiocyanate and potassium thiocyanate, which has twice the solubility in water. Silver thiocyanate may be used as well; the precipitation of insoluble silver halides help simplify workup. Treatment of isopropyl bromide with sodium thiocyanate in a hot ethanolic solution affords isopropyl thiocyanate.[4] Protonation of sodium thiocyanate affords isothiocyanic acid, S=C=NH (pKa = -1.28).[5] This species is generated in situ from sodium thiocyanate; it adds to organic amines to afford derivatives of thiourea.[6]

References

  1. ^ Sodium thiocyanate, chemicalland21.com
  2. ^ Schwan, A. L. (2001). Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rs109. 
  3. ^ van Rooyen, P. H.; Boeyens, J. C. A. (1975). "Sodium thiocyanate". Acta Crystallographica B31 (12): 2933–2934. doi:10.1107/S0567740875009326. 
  4. ^ Shriner, R. L. (1943). "Isopropyl Thiocyanate". Org. Synth. ; Coll. Vol. 2, p. 366 
  5. ^ Chiang, Y.; Kresge, A. J. (2000). "Determination of the Acidity Constant of Isothiocyanic Acid in Aqueous Solution". Canadian Journal of Chemistry 78 (12): 1627–1628. doi:10.1139/cjc-78-12-1627. 
  6. ^ Allen, C. F. H.; VanAllan, J. (1955). "2-Amino-6-Methylbenzothiazole". Org. Synth. ; Coll. Vol. 3, p. 76