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2-Iminothiolane
Free base form	Hydrochloride form
Names
	IUPAC name Dihydro-2(3H)-thiophenimine hydrochloride
	Other names Traut's reagent; 2-Thiolanimine hydrochloride;
Identifiers
CAS Number	4781-83-3 (Hydrochloride);
PubChem CID	13166855;
Properties
Chemical formula	C4H7NS·HCl
Molar mass	137.63 (Hydrochloride); 101.17 (Free base)
Appearance	Powder
Boiling point	198–201 °C (388–394 °F; 471–474 K) (Hydrochloride)
Solubility in water	100 mg/mL
	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 witih primary amines efficienty at pH 7 to 9, creating aminidine 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.^[2]

It also reacts with aliphatic and phenolic hydroxyl groups at high pH, albeit at a much slower rate.^[3]

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

References

^ ^a ^b ^c Sigma-Aldrich Co., product no. I6256. Retrieved on July 06, 2015.
^ R. R. Traut et al., Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome., Biochemistry 12, 1973, pg. 3266–3273, PMID 4581787.
^ "Traut's Reagent Instructions" (PDF). Thermo Scientific. Retrieved 2015-07-08.

Category:Sulfur compounds Category:Imines

[Sigma-1] Sigma-Aldrich Co., product no. I6256. Retrieved on July 06, 2015.

[2] R. R. Traut et al., Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome., Biochemistry 12, 1973, pg. 3266–3273, PMID 4581787.

[3] "Traut's Reagent Instructions" (PDF). Thermo Scientific. Retrieved 2015-07-08.

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