Dibromodiethyl sulfide

Dibromodiethyl sulfide is a chemical like mustard gas in which bromine replaces chlorine. It is very irritating as a vapour.[1]

Dibromodiethyl sulfide
Names
Preferred IUPAC name
1-Bromo-2-[(2-bromoethyl)sulfanyl]ethane
Other names
Di(2-Bromoethyl) sulfide; bis(beta-bromethyl)sulfide; 2,2'-dibromodiethyl sulfide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H8Br2S/c5-1-3-7-4-2-6/h1-4H2
    Key: YYWACUFAVLSCPF-UHFFFAOYSA-N
  • C(CBr)SCCBr
Properties
Density 1.838
Boiling point 258.3 °C (496.9 °F; 531.5 K)
1.566
Hazards
Flash point 110 °C (230 °F; 383 K)
Related compounds
Related compounds
Dibromodiethyl sulfoxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Production

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Dibromodiethyl sulfide can be produced by the reaction of bromine with thiodiglycol.[1]

Properties

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Dibromodiethyl sulfide takes the form of white crystals. The melting point is between 31 and 34°C. It decomposes when heated to 240°C.[1]

The fungus Tyromyces palustris can split the molecule at the sulfur.[2]

References

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  1. ^ a b c Lewis, Robert A. (2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 440. ISBN 978-1-118-13515-0.
  2. ^ El-Gendy, Nour Shafik; Nassar, Hussein Mohamed Nabil (2018). Biodesulfurization in Petroleum Refining. John Wiley & Sons. p. 776. ISBN 978-1-119-22408-2.