Thiodiglycol

Thiodiglycol

Names
IUPAC name 2-(2-Hydroxyethylsulfanyl)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 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:75184 N
ChEMBL	ChEMBL444480 Y
ChemSpider	13881956 Y
ECHA InfoCard	100.003.523
PubChem	5447
UNII	9BW5T43J04 Y
InChI InChI=1S/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2 Y Key: YODZTKMDCQEPHD-UHFFFAOYSA-N Y InChI=1/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2 Key: YODZTKMDCQEPHD-UHFFFAOYAC
SMILES OCCSCCO
Properties
Chemical formula	C4H10O2S
Molar mass	122.19 g/mol
Appearance	Clear to pale-yellow liquid
Melting point	−16 °C (3 °F; 257 K)
Boiling point	165 °C (329 °F; 438 K) at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Thiodiglycol, or bis(2-hydroxyethyl)sulfide (also known as 2,2-thiodiethanol or TDE), 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.

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.

A relatively recent use (as of 2006) of thiodiglycol is as a mounting medium in microscopy. The ability to vary the refractive index of the medium by varying the concentration of TDE in an aqueous solution, plus its relative lack of toxicity makes it highly desirable for such use. The refractive index of the solution can be varied anywhere from near that of water (1.333) to that of glass (1.518).