Furan-2-ylmethanethiol

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Furan-2-ylmethanethiol
Kekulé, skeletal formula of furan-2-ylmethanethiol
Ball-and-stick model
Names
Preferred IUPAC name
(Furan-2-yl)methanethiol
Other names
  • Furan-2-ylmethanethiol
  • (2-Furanyl)methylmercaptan
  • 2-Furfurylmercaptan
  • Furfuryl mercaptan
  • 2-Furfurylthiol
  • Furfuryl thiol
  • 2-Furylmethanethiol
  • 2-Furylmethyl mercaptan
  • 2-(Mercaptomethyl)furan
Identifiers
3D model (JSmol)
383594
ChemSpider
ECHA InfoCard 100.002.390
EC Number 202-628-2
MeSH furfuryl+mercaptan
RTECS number LU2100000
UN number 3336
Properties
C5H6OS
Molar mass 114.16 g·mol−1
Appearance Colourless liquid
Odor Roasted coffee, Caramel, Sulfurous, Waxy
Density 1.132 g cm−3
Boiling point 155 °C; 311 °F; 428 K
Vapor pressure 531 Pa
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H226
Flash point 45 °C (113 °F; 318 K)
Lethal dose or concentration (LD, LC):
100-200 mg kg−1 (mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Furan-2-ylmethanethiol is an organic compound containing a furan substituted with a sulfanylmethyl group. It is a clear colourless liquid when pure, but it becomes yellow coloured upon prolonged standing. It possesses a strong odour of roasted coffee and a bitter taste. It is a key component of the aroma of roasted coffee.

Synthesis[edit]

Furan-2-ylmethanol is easily prepared by reacting furfuryl alcohol with thiourea in hydrochloric acid via an intermediate isothiouronium salt which is hydrolized to the thiol by heating with sodium hydroxide.[1]

Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)






References[edit]

  1. ^ Preparation of furfuryl mercaptane http://www.orgsyn.org/demo.aspx?prep=CV4P0491