Furan-2-ylmethanethiol

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	98-02-2  Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	383594
ChemSpider	7085  Y
ECHA InfoCard	100.002.390
EC Number	202-628-2
MeSH	furfuryl+mercaptan
PubChem CID	7363
RTECS number	LU2100000
UNII	29W096TCPG  Y
UN number	3336
CompTox Dashboard (EPA)	DTXSID7052654
InChI InChI=1S/C5H6OS/c7-4-5-2-1-3-6-5/h1-3,7H,4H2 Y Key: ZFFTZDQKIXPDAF-UHFFFAOYSA-N Y
SMILES 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
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  YN ?) 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)

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.