Thiirane

Ethylene sulfide

Clear, colorless liquid with an unpleasant odor

Liquid

1.01 g · cm -3

55-56 ° C

287 hPa ( 20 ° C)

1.495 at 20 ° C.

Risk

178 mg · kg -1 ( LD50, rat, oral)

51.6 kJ / mol

Template: Infobox chemical / molecular formula search available

Thiirane, also called ethylene sulfide, is a sulfur- saturated three -membered heterocycle and thus the simplest representative of the group of substances thiiranes.

Representation

Displaying thiirane is achieved by the reaction of ethylene oxide with thiourea in an aqueous medium with cooling. This produces thiirane and urea.

A further possibility is the reaction of ethylene carbonate with potassium thiocyanate, in the next to occur thiirane carbon dioxide and potassium cyanate.

Properties

Ethylene sulfide is a liquid at room temperature compound having a boiling point of 55-56 ° C. The bond length between carbon and sulfur is 181.9 pm, 149.2 pm between two carbons. The bond angle at the sulfur atom is 65 ° 48 '.

Reactions

Thiirane reacts with nucleophiles under ring opening. It can therefore be used for the synthesis of terminal thiols. As nucleophiles such as amines or thiols can act.

With imines it reacts with the formation of N- Alkyltetrahydroimidazolen.

However, the sulfur atom of the thiirane has the ability to serve even as a nucleophile.