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Thiodiglycol

Thiodiglycol


IUPAC name	2-(2-Hydroxy-ethylsulfanyl)-ethanol
Other names	2,2'-Thiodiethanol, β,β'-dihydroxydiethyl sulfide, β-thiodiglycol, thiodiethylene glycol, β-hydroxyethyl sulfide, 2-hydroxyethyl sulfide, bis(β-hydroxyethyl)sulfide, Glyecine A, Kromfax Solvent, Tedegyl
Identifiers
CAS number	111-48-8
PubChem	5447
SMILES	OCCSCCO
Properties
Molecular formula	C₄H₁₀O₂S
Molar mass	122.19 g/mol
Appearance	Clear to pale-yellow liquid
Melting point	-16 °C, 257 K, 3 °F
Boiling point	165 °C at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Thiodiglycol, or bis(2-hydroxyethyl)sulfide, is a viscous, clear to pale-yellow liquid used as a solvent. Its chemical formula is C₄H₁₀O₂S, or HOCH₂CH₂SCH₂CH₂OH. It is miscible with acetone, alcohols, and chloroform. It is soluble in benzene, ether, and tetrachloromethane.

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Thiodiglycol is manufactured by reaction of 2-chloroethanol with sodium sulfide. It is structurally similar to diethylene glycol.

Thiodiglycol has both polar and nonpolar solvent properties. It is used as a solvent in a variety of applications ranging from dyeing textiles to inks in some ballpoint pens. In chemical synthesis, it is used as a building block for protection products, dispersants, fibers, plasticizers, rubber accelerators, pesticides, dyes, and various other organic chemicals. In the manufacture of polymers, it is used as a chain transfer agent. As an antioxidant, it is used as an additive in lubricants.

Thiodiglycol is a Chemical Weapons Convention schedule 2 chemical used in the production of sulfur-based blister agents such as mustard gas. Thiodiglycol is also a product of the hydrolysis of mustard gas. It can be detected in the urine of casualties.

Categories: Alcohols | Solvents | Thioethers