Thiourea dioxide

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Thiourea dioxide
Names
IUPAC name
Amino(imino)methanesulfinic acid
Other names
Formamidine sulfinic acid
Formamidinesulfinic acid
Thiourea sulfone
Thiox
Properties
CH4N2O2S
Molar mass 108.12 g/mol
Appearance White or slight yellowish solid
Odor Odorless
Density 1.706 g/cm3[1]
Melting point 126 °C (259 °F; 399 K) (decomposes)
Boiling point Decomposes
3.0 g/100 mL
Hazards
Safety data sheet Sigma-Aldrich
Related compounds
Related compounds
Thiourea
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Thiourea dioxide (CH4N2O2S) is an organosulfur compound that is used as reductive bleaching in the textile industry. The compound exhibits tautomerism.

Properties

Chemical

Thiourea dioxide can be used to reduce ketones to secondary alcohols.[2]

Physical

Thiourea dioxide is a white solid, poorly soluble in water.

Availability

Thiourea dioxide is sold by lab suppliers.

Preparation

Thiourea dioxide can be easily prepared by the oxidation of thiourea with hydrogen peroxide.

(NH2)2CS + 2 H2O2 → (NH)(NH2)CSO2H + 2 H2O

Chlorine dioxide can also be used.

Projects

  • Reduction of aromatic nitroaldehydes and nitroketones to nitroalcohols

Handling

Safety

Thiourea dioxide is not very toxic, but it is irritating to skin and mucous membranes.

Storage

In closed bottles.

Disposal

Thiourea dioxide can be strongly diluted with water and poured down the drain.

Heating it in a kiln/oven is another possibility, as the decomposition produces carbon dioxide, sulfur dioxide, nitrogen, ammonia.

References

  1. Sullivan; Hargreaves; Acta Crystallographica; vol. 15; (1962); p. 675
  2. https://www.sciencedirect.com/science/article/pii/S0040403901843203

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