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1 Synthesis  





2 References  














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)

  • Interactive image
  • 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=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

    Chemical formula

    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:

    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−1 (mouse)

    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    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.[1][2]

    Synthesis[edit]

    Furan-2-ylmethanethiol is easily prepared by reacting furfuryl alcohol with thioureainhydrochloric acid via an intermediate isothiouronium salt which is hydrolized to the thiol by heating with sodium hydroxide.[3]

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

    References[edit]

    1. ^ Parker JK, Kelly CE, Gane SB (5 February 2021). "Molecular Mechanism of Parosmia". p. 21251085. medRxiv 10.1101/2021.02.05.21251085.
  • ^ Devlin H (25 May 2022). "Scientists identify 'trigger molecule' for Covid-related changes to smell". The Guardian.
  • ^ "Preparation of furfuryl mercaptane". Organic Syntheses. 35: 66. 1955. doi:10.15227/orgsyn.035.0066.
  • t
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  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Furan-2-ylmethanethiol&oldid=1170040702"

    Categories: 
    Aromatic compound stubs
    Heterocyclic compound stubs
    Flavors
    Thiols
    2-Furyl compounds
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    This page was last edited on 12 August 2023, at 21:34 (UTC).

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