Thiodiglycol

chembox new
ImageFile = Thiodiglycol-2D-skeletal.png ImageSize =
ImageFile1 = Thiodiglycol-3D-vdW.png ImageSize1 =
IUPACName = 2-(2-Hydroxy-ethylsulfanyl)-ethanol
OtherNames = 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
Section1 = Chembox Identifiers
Abbreviations =
CASNo = 111-48-8
EINECS =
PubChem = 5447
SMILES = OCCSCCO
InChI =
RTECS =
MeSHName =
ChEBI =
KEGG =
ATCCode_prefix =
ATCCode_suffix =
ATC_Supplemental =
Section2 = Chembox Properties
Formula = Carbon₄Hydrogen₁₀Oxygen₂Sulfur
MolarMass = 122.19 g/mol
Appearance = Clear to pale-yellow liquid
Density =
MeltingPtC = -16
Melting_notes =
BoilingPt = 165 °C at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure
Boiling_notes =
Solubility =
SolubleOther =
Solvent =
pKa =
pKb =
Section7 = Chembox Hazards
EUClass =
EUIndex =
MainHazards =
NFPA-H =
NFPA-F =
NFPA-R =
NFPA-O =
RPhrases =
SPhrases =
RSPhrases =
FlashPt =
Autoignition =
ExploLimits =
PEL =

Thiodiglycol, or bis(2-hydroxyethyl)sulfide, is a viscous, clear to pale-yellow liquid used as a solvent. Its chemical formula is Carbon₄Hydrogen₁₀Oxygen₂Sulfur, or HOCH₂CH₂SCH₂CH₂OH. It is miscible with acetone, alcohols, and chloroform. It is soluble in benzene, ether, and tetrachloromethane.

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.

External links

* [http://cbwinfo.com/Chemical/Precursors/p1.html Blister agent degradation product/precursor: Thiodiglycol]
* [http://cbwinfo.com/General/Proliferation/Thiodiglycol.html From textile sizing to poisoning: how thiodiglycol was made to lose its way]