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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
CAS Number
3D model (JSmol)
Beilstein Reference 383594
ChemSpider
ECHA InfoCard 100.002.390 Edit this at Wikidata
EC Number
  • 202-628-2
MeSH furfuryl+mercaptan
PubChem CID
RTECS number
  • LU2100000
UNII
UN number 3336
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6OS/c7-4-5-2-1-3-6-5/h1-3,7H,4H2Key: ZFFTZDQKIXPDAF-UHFFFAOYSA-N
SMILES
  • SCc1ccco1
  • SCC1=CC=CO1
Properties
Chemical formula C5H6OS
Molar mass 114.16 g·mol
Appearance Colourless liquid
Odor Roasted coffee, Caramel, Sulfurous, Waxy
Density 1.132 g cm
Boiling point 155 °C; 311 °F; 428 K
Vapor pressure 531 Pa
Hazards
GHS labelling:
Pictograms GHS02: Flammable
Signal word Warning
Hazard statements H226
Flash point 45 °C (113 °F; 318 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 100-200 mg kg (mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Furan-2-ylmethanethiol (2-Furanmethanethiol) 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. It has been identified as a trigger molecule for parosmia following COVID-19 infection.

Synthesis

Furan-2-ylmethanethiol 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.

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

References

  1. Parker JK, Kelly CE, Gane SB (5 February 2021). "Molecular Mechanism of Parosmia". p. 21251085. medRxiv 10.1101/2021.02.05.21251085.
  2. Devlin H (25 May 2022). "Scientists identify 'trigger molecule' for Covid-related changes to smell". The Guardian.
  3. "Preparation of furfuryl mercaptane". Organic Syntheses. 35: 66. 1955. doi:10.15227/orgsyn.035.0066.
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