1-(2-Hydroxyethyl)-1H-tetrazol-5-ylthiol sodium salt
[CAS# 64350-77-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol salt
• Name: 1-(2-Hydroxyethyl)-1H-tetrazol-5-ylthiol sodium salt
• Synonyms: 1,2-Dihydro-1-(2-hydroxyethyl)-5H-tetrazole-5-thione monosodium salt
• Molecular Formula: C₃H₅N₄OS^.Na
• Molecular Weight: 168.15
• CAS Registry Number: 64350-77-2
• SMILES: C(CO)N1C(=NN=N1)[S-].[Na+]

Discovory and Applicatios

1,2-Dihydro-1-(2-hydroxyethyl)-5H-tetrazole-5-thione monosodium salt is an ionic tetrazole-based heterocyclic compound, more formally known as sodium 1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiolate. It consists of a tetrazole ring (a five-membered ring containing four nitrogen atoms) substituted at the 1-position with a 2-hydroxyethyl group and featuring a thione (C=S) group at the 5-position, with the sodium cation balancing the thiolate anion. The molecular formula is C₃H₅N₄OS·Na, and it typically appears as a white to off-white crystalline solid. Its structure places it within the class of tetrazole-thione salts, which are derivatives of tetrazole where a thiocarbonyl replaces the carbonyl or amino functionality, and the thione sulfur is deprotonated to form a sodium salt. Commercial listings identify it under several synonyms including sodium 1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiolate and 1-(2-hydroxyethyl)-1H-tetrazol-5-thiol sodium salt.

Compounds of this class are generally used as chemical intermediates in synthetic chemistry and pharmaceutical manufacturing. The 2-hydroxyethyl substituted tetrazole thiolate can serve as a reactive intermediate in the synthesis of more complex heterocyclic structures or drug intermediates, particularly because the tetrazole ring is a common bioisostere for carboxylic acids in medicinal chemistry due to similar acidity and coordination properties. Tetrazole derivatives are also used as ligands in coordination chemistry, building blocks for agrochemical and pharmaceutical research, and precursors for materials with specialized properties. While this specific sodium tetrazole thiolate is not widely discussed in traditional academic literature, analogous tetrazole and tetrazole-thione derivatives have been studied for their reactivity and applications as synthetic building blocks.

The tetrazole ring system itself is a well-known heterocycle in organic chemistry, consisting of a five-membered ring containing four nitrogen atoms, and can act as a versatile functional group in organic synthesis and materials science. Tetrazoles are used as acid surrogates in medicinal compounds, energetic materials, and as ligands in coordination complexes, reflecting the broader utility of tetrazole chemistry, although the specific 5-thione sodium salt discussed here is primarily of interest as a reactive intermediate rather than a final product in these applications.

References

Wei C-X, Bian M, Gong G-H (2015) Tetrazolium compounds: synthesis and applications in medicine. Molecules 20(4) 5528–5553 DOI: 10.3390/molecules20045528

MDPI Neochoritis CG, Zhao T, Dömling A (2019) Tetrazoles via multicomponent reactions. Chemical Reviews 119(3) 1970–2042 DOI: 10.1021/acs.chemrev.8b00564

ACS Publications Malik MA, Wani MY, Al-Thabaiti SA, Sheikh RA (2013) Tetrazoles as carboxylic acid isosteres: chemistry and biology. Journal of Inclusion Phenomena and Macrocyclic Chemistry 76 23–48DOI: 10.1007/s10847-013-0334-x