2-Iminothiolane

2-Iminothiolane

Free base form Hydrochloride form
Names
Preferred IUPAC name Thiolan-2-imine
Other names Traut's reagent 2-Thiolanimine
Identifiers
CAS Number	6539-14-6 4781-83-3 (HCl)
ECHA InfoCard	100.226.745
PubChem CID	433941 13166855 (HCl)
CompTox Dashboard (EPA)	DTXSID60524217
Properties
Chemical formula	C4H7NS C4H7NS·HCl
Molar mass	101.17 (free base) 137.63 (HCl)
Appearance	Powder
Melting point	198–201 °C (388–394 °F; 471–474 K) (HCl)
Solubility in water	100 mg/mL (HCl)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Iminothiolane is a cyclic thioimidate compound also known as Traut's reagent. It is a thiolating reagent that reacts with primary amine groups, such as those of amino acids, to form sulfhydryl groups.

Application

2-Iminothiolane reacts with primary amines efficiently at pH 7 to 9, creating amidine compounds with a sulfhydryl group. Thus it allows for crosslinking or labeling of molecules such as proteins through use of disulfide or thioether conjugation. It was first used to thiolate a subunit of ribosome in E. coli in 1973 by Robert Traut, its namesake, and his colleagues.

It also reacts with aliphatic and phenolic hydroxyl groups at high pH, albeit at a much slower rate.

The reaction of 2-iminothiolane with an amine group of a peptide.