Furan-2-ylmethanethiol

Furan-2-ylmethanethiol
Kekulé, skeletal formula of furan-2-ylmethanethiol
Kekulé, skeletal formula of furan-2-ylmethanethiol
Ball-and-stick model
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
UNII
UN number 3336
  • InChI=1S/C5H6OS/c7-4-5-2-1-3-6-5/h1-3,7H,4H2 checkY
    Key: ZFFTZDQKIXPDAF-UHFFFAOYSA-N checkY
  • SCc1ccco1
  • SCC1=CC=CO1
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 labelling:
GHS02: Flammable
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 (2-furanmethanethiol) is an organosulfur compound. It is classified as a furan substituted with a methylthiol group. It is a colourless liquid, but impure samples can appear yellow. It possesses a strong odour of roasted coffee[1] and a bitter taste. It is a key component of the aroma of roasted coffee. It has been identified as a trigger molecule for parosmia following COVID-19 infection.[2][3]

Synthesis

Furan-2-ylmethanethiol is prepared by treating furfuryl alcohol with thiourea in hydrochloric acid via an intermediate isothiouronium salt, which is hydrolized to the thiol by heating with sodium hydroxide.[4]

Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)
Synthesis of furfuryl mercaptane (Furan-2-ylmethanethiol)

References

  1. ^ Viani, Rinantonio; Petracco, Marino (2007). "Coffee". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a07_315.pub2. ISBN 978-3-527-30385-4.
  2. ^ Parker JK, Kelly CE, Gane SB (5 February 2021). "Molecular Mechanism of Parosmia". p. 21251085. medRxiv 10.1101/2021.02.05.21251085.
  3. ^ Devlin H (25 May 2022). "Scientists identify 'trigger molecule' for Covid-related changes to smell". The Guardian.
  4. ^ "Preparation of Furfuryl mercaptan". Organic Syntheses. 35: 66. 1955. doi:10.15227/orgsyn.035.0066.
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