:Sodium thiocyanate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 476996662
| ImageFile = Sodium thiocyanate.png
| ImageSize = 160px
| ImageFileL1 = Sodium-3D.png
| ImageNameL1 = The sodium cation
| ImageFileR1 = Thiocyanate-3D-vdW.png
| ImageSizeR1 = 140px
| ImageNameR1 = The thiocyanate anion (space-filling model)
| ImageFile2 = Sodium thiocyanate.jpg
| IUPACName = Sodium thiocyanate
| OtherNames = Sodium rhodanide
Sodium sulfocyanate
Sodium rhodanate
Thiocyanic acid, sodium salt
|Section1={{Chembox Identifiers
| CASNo = 540-72-7
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10443
| Beilstein = 3594965
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30952
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1644028
| ChEMBL2_Ref = {{ebicite|correct|EBI}}
| ChEMBL2 = 84336
| ChEMBL3_Ref = {{ebicite|correct|EBI}}
| ChEMBL3 = 1078613
| Gmelin = 1249825
| PubChem = 516871
| EINECS = 208-754-4
| RTECS = XL2275000
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5W0K9HKA05
| SMILES = [Na+].[S-]C#N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CHNS.Na/c2-1-3;/h3H;/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VGTPCRGMBIAPIM-UHFFFAOYSA-M
| InChIKey1 = VGTPCRGMBIAPIM-UHFFFAOYSA-M
| InChI = 1S/CHNS.Na/c2-1-3;/h3H;/q;+1/p-1
| InChIKey = VGTPCRGMBIAPIM-REWHXWOFAB
}}
|Section2={{Chembox Properties
| Formula = NaSCN
| MolarMass = 81.072 g/mol
| Appearance = deliquescent colorless crystals
| Density = 1.735 g/cm3
| MeltingPtC = 287
| BoilingPtC = 307
| BoilingPt_notes = decomposes
| Solubility = 139 g/100 mL (21 °C)
225 g/100 mL (100 °C)
| SolubleOther = soluble in acetone, alcohols, ammonia, SO2
| Solvent =
| pKa = −1.28
| RefractIndex = 1.545
}}
|Section3={{Chembox Structure
| CrystalStruct = orthorhombic
}}
|Section5={{Chembox Thermochemistry
| DeltaHf =
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0675.htm ICSC 0675]
| NFPA-H = 2
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|312|332|412}}
| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+312|304+340|305+351+338|310|312|322|330|337+313|363|501}}
| FlashPt =
| PEL =
| LD50 = 764 mg/kg (oral, rat)[http://chemicalland21.com/industrialchem/organic/SODIUM%20THIOCYANATE.htm Sodium thiocyanate], chemicalland21.com
}}
|Section8={{Chembox Related
| OtherCations = Lithium thiocyanate
Potassium thiocyanate
Ammonium thiocyanate
| OtherAnions = Sodium cyanate
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.{{cite book | author = Schwan, A. L. | title = Encyclopedia of Reagents for Organic Synthesis | year = 2001 | publisher = John Wiley & Sons | location = New York | doi = 10.1002/047084289X.rs109}} 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.{{cite journal | last1 = van Rooyen | first1 = P. H. | last2 = Boeyens | first2 = J. C. A. | author2-link = Jan C. A. Boeyens | title = Sodium thiocyanate | journal = Acta Crystallographica | year = 1975 | volume = B31 | issue = 12 | pages = 2933–2934 | doi = 10.1107/S0567740875009326| doi-access = free | bibcode = 1975AcCrB..31.2933V }} 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.{{cite journal |doi=10.15227/orgsyn.011.0092|title=Isopropyl Thiocyanate|journal=Organic Syntheses|year=1931|volume=11|page=92|author=R. L. Shriner}} Protonation of sodium thiocyanate affords isothiocyanic acid, S=C=NH (pKa = −1.28).{{cite journal |author1=Chiang, Y. |author2=Kresge, A. J. | title = Determination of the Acidity Constant of Isothiocyanic Acid in Aqueous Solution | journal = Canadian Journal of Chemistry | year = 2000 | volume = 78 | issue = 12 | pages = 1627–1628 | doi = 10.1139/cjc-78-12-1627}} Isothiocyanic acid, typically generated in situ from sodium thiocyanate, adds to anilines to afford 2-aminobenzothiazoles.{{OrgSynth | author = Allen, C. F. H.; VanAllan, J.| title = 2-Amino-6-Methylbenzothiazole | volume = 22 | page = 16 | year = 1942 | doi = 10.15227/orgsyn.022.0016}}
Related compounds
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.