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Sodium diethyldithiocarbamate

(Redirected from Diethyldithiocarbamate)

Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2. It is a pale yellow, water soluble salt.

Sodium diethyldithiocarbamate
Names
Preferred IUPAC name
Sodium diethylcarbamodithioate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.192 Edit this at Wikidata
UNII
  • InChI=1S/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1 checkY
    Key: IOEJYZSZYUROLN-UHFFFAOYSA-M checkY
  • InChI=1/C5H11NS2.Na/c1-3-6(4-2)5(7)8;/h3-4H2,1-2H3,(H,7,8);/q;+1/p-1
    Key: IOEJYZSZYUROLN-REWHXWOFAF
  • [Na+].[S-]C(=S)N(CC)CC
Properties
C5H10NS2Na
Molar mass 171.259 g/mol (anhydrous)
Appearance White, slightly brown, or slightly pink crystalline solid
Density 1.1 g/cm3
Melting point 95 °C (203 °F; 368 K)
Soluble
Solubility soluble in alcohol, acetone
insoluble in ether, benzene
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful
Related compounds
Other cations
 Silver diethyldithiocarbamate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation

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Sodium diethyldithiocarbamate typically crystallizes from water as the trihydrate NaS2CN(C2H5)2.3H2O. The anhydrous salt and the trihydrate are often used interchangeably.[1]

Sodium diethyldithiocarbamate is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide:

CS2 + HN(C2H5)2 + NaOH → NaS2CN(C2H5)2 + H2O

Other dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide. They are used as chelating agents for transition metal ions and as precursors to herbicides and vulcanization reagents.

Reactions

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Iron tris(diethyldithiocarbamate), a black solid that is soluble in organic solvents, is a representative complex of diethyldithiocarbamate.

Oxidation of sodium diethyldithiocarbamate gives the disulfide, also called a thiuram disulfide (Et = ethyl):

2 NaS2CNEt2 + I2 → (S2CNEt2)2 + 2 NaI

Dithiocarbamates are nucleophiles and thus can be alkylated. Even dichloromethane suffices:[2]

2 NaS2CNEt2 + CH2Cl2 → CH2(S2CNEt2)2 + 2 NaCl

Diethyldithiocarbamate reacts with many metal salts to give transition metal dithiocarbamate complexes. The ligands coordinate via the two sulfur atoms. Other more complicated bonding modes are known including binding as unidentate ligand and a bridging ligand using one or both sulfur atoms.[3]

Laboratory and practical use

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By the technique of spin trapping, complexes of dithiocarbamates with iron provide one of the very few methods to study the formation of nitric oxide (NO) radicals in biological materials. Although the lifetime of NO in tissues is too short to allow detection of this radical itself, NO readily binds to iron-dithiocarbamate complexes. The resulting mono-nitrosyl-iron complex (MNIC) is stable, and may be detected with Electron Paramagnetic Resonance (EPR) spectroscopy.[4][5][6]

The zinc chelation of diethyldithiocarbamate inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, an initial step in cancer metastasis and angiogenesis.[7]

Diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.[7]

References

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  1. ^ Mereiter K, Preisinger A, Mikenda W, Steidl H (1985). "Hydrogen bonds in sodium dialkylthiocarbamate hydrates. X-ray diffraction and vibrational spectroscopic study". Inorganica Chimica Acta. 98 (2): 71–78. doi:10.1016/s0020-1693(00)84914-2.
  2. ^ Heckley PR, Holah DG, Hughes AN, Leh F (1970). "Reactions of Sodium N,N-Diethyldithiocarbamate with Some Organic Solvents". Canadian Journal of Chemistry. 48 (24): 3827–3830. doi:10.1139/v70-645.
  3. ^ Cotton, F. Albert, Wilkinson, Geoffrey, Murillo, Carlos A., Bochmann, Manfred (1999), Advanced Inorganic Chemistry (6th ed.), New York: Wiley-Interscience, ISBN 0-471-19957-5
  4. ^ Henry Y.; Guissani A.; Ducastel B. (eds); "Nitric oxide research from chemistry to biology: EPR spectroscopy of nitrosylated compounds." Landes, Austin 1997.
  5. ^ Vanin A, Huisman A, van Faassen E (2002). "Iron dithiocarbamate as spin trap for nitric oxide detection: Pitfalls and successes". Nitric Oxide, Part D: Oxide Detection, Mitochondria and Cell Functions, and Peroxynitrite Reactions. Methods in Enzymology. Vol. 359. pp. 27–42. doi:10.1016/s0076-6879(02)59169-2. ISBN 978-0-12-182262-0. PMID 12481557.
  6. ^ van Faassen E.E.; Vanin A.F. (eds); "Radicals for life: The various forms of nitric oxide." Elsevier, Amsterdam 2007.
  7. ^ a b diethyldithiocarbamate National Cancer Institute - Drug Dictionary

Further reading

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