Dibromoethyl sulphide

The catalysed -elimination of hydrogen bromide from 2-bromoethyl and 1,2-dibromoethyl sulphides, using 9.1.1 or 9.1.2, provides a convenient route to vinyl and alkynyl sulphides, respectively [17, 18], which, as their sulphoxides or sulphones, have considerable utility as dienophiles. Aryl vinyl ethers (>90%) have been obtained by analogous procedures from 2-chloroethyl ethers [19]. 

Dibromoethyl sulphide is less toxic than dichloroethyl sulphide ... 

Includes Perchloromethyl mercaptan Dichloroethyl sulphide. Dibromoethyl sulphide. Sulphoxides Sulphones. ... 

The monosubstituted derivatives, ethyl ]8 chloroethyl sulphide and ethyl ]8 bromoethyl sulphide, are weak in toxicity, as is also the disubstituted compound aa dichloroethyl sulphide. The disubstituted derivative with both the halogen atoms in the )8 position, jSjS dichloroethyl sulphide, however, is powerfully toxic and vesicant it is more commonly known as " Mustard Gas" Other derivatives analogous to /SjS dichloroethyl sulphide have been prepared, such as /S/3 dibromoethyl sulphide and /3/S diiodoethyl sulphide, which have similar physiopathological properties, as well as homologues of /3/S dichloroethyl sulphide such as /3/3 dichloropropyl sulphide (I) and /3/3 dichlorobutyl sulphide (II) ... 

Rona, Z. gts. expt. Med., 1921,13, 16, also gives the velocity of hydrolysis of substances similar to dichloroethyl sulphide, like tetrachloroethyl sulphide, dibromoethyl sulphide, etc. 

S dibromoethyl sulphide was examined as a possible war gas only in the post-war period (Muller). Although having similar physiopathological properties to dichloroethyl sulphide, it has some disadvantages as a war gas, especially from the manufacturing point of view (Hanslian). 

Steinkopf prepared dibromoethyl sulphide by the abtion of phosphorus tribromide on thiodiglycol. However, it may be prepared more simply by saturating an aqueous solution of thiodiglycol with hydrobromic acid. ... 

Dibromoethyl sulphide forms white crystals which melt at 31° to 34° C. (Steinkopf). It boils at ordinary pressure at 240° C. with decomposition and at i mm. pressure at 115 5° 0. 

On treating a hot solution of dibromoethyl sulphide in chloroform with benzoyl hydrogen peroxide, dibromoethyl sulphoxide is formed ... 

This forms glittering crystals melting at ioo° to ioi° CT It may also be obtained by the action of concentrated nitric acid on dibromoethyl sulphide by first maintaining the temperature at o° C. and then allowing it to rise to room temperature to complete the reaction. ... 

Chromic anhydride and dilute sulphuric acid react at water-bath temperature with dibromoethyl sulphide to produce dibromoethyl sulphone ... 

Dibromoethyl sulphide, like the dichloro-compound, easily reacts with primary amines, forming the corresponding thiazane derivatives (Burrows). 

The persistence of dibromoethyl sulphide on the ground is greater than that of dichloroethyl sulphide only in dry weather. 

It is produced in the reaction between dichloroethyl sulphide and the Grignard reagent (see p. 248), and also, together with dithiane methiodide, by the action of methyl iodide on dichloroethyl or dibromoethyl sulphide. It has also been obtained by the action of hydriodic acid on an aqueous solution of divinyl sulphide. ... 

---