Furan-2-ylmethanethiol
Names | |
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Preferred IUPAC name (Furan-2-yl)methanethiol | |
Other names
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Identifiers | |
CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 383594 |
ChemSpider |
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ECHA InfoCard | 100.002.390 |
EC Number |
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MeSH | furfuryl+mercaptan |
PubChem CID |
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RTECS number |
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UNII |
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UN number | 3336 |
CompTox Dashboard (EPA) |
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InChI
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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 | |
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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 YN ?) 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
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.[3]
References
- ^ 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.
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