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Revision as of 12:16, 26 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CASNo').← Previous edit		Latest revision as of 21:34, 12 August 2023 edit undoTrappist the monk (talk | contribs)Administrators479,857 editsm →top: Convert {{Cite document}} (1×) to {{Cite medRxiv}};Tag: AWB
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			{{Use dmy dates|date=December 2021}}
	{{Chembox		{{Chembox
			| Verifiedfields = changed
	| SystematicName = Furan-2-ylmethanethiol<ref>{{Cite web|title = furfuryl mercaptan - PubChem Public Chemical Database|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7363|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information|at = Descriptors Computed from Structure}}</ref>
			| Watchedfields = changed
	| OtherNames = (2-Furanyl)methylmercaptan{{Citation needed|date = September 2011}}<br />
			| verifiedrevid = 457473820
	2-Furfurylmercaptan{{Citation needed|date = September 2011}}<br />
			| PIN = (Furan-2-yl)methanethiol
	Furfuryl mercaptan{{Citation needed|date = September 2011}}<br />
			| OtherNames = {{Unbulleted list|Furan-2-ylmethanethiol|(2-Furanyl)methylmercaptan|2-Furfurylmercaptan|Furfuryl mercaptan|2-Furfurylthiol|Furfuryl thiol|2-Furylmethanethiol|2-Furylmethyl mercaptan|2-(Mercaptomethyl)furan}}
	2-Furfurylthiol{{Citation needed|date = September 2011}}<br />
	Furfuryl thiol{{Citation needed|date = September 2011}}<br />
	2-Furylmethanethiol{{Citation needed|date = September 2011}}<br />
	2-Furylmethyl mercaptan{{Citation needed|date = September 2011}}<br />
	2-(Mercaptomethyl)furan{{Citation needed|date = September 2011}}
	| ImageFile = 2-Furanmethanethiol.svg		| ImageFile = 2-Furanmethanethiol.svg
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageSize = 244		| ImageSize = 180
	| ImageName = Kekulé, skeletal formula of furan-2-ylmethanethiol		| ImageName = Kekulé, skeletal formula of furan-2-ylmethanethiol
			| ImageFile2 = Furan-2-ylmethanethiol.png
⚫	| Section1 = {{Chembox Identifiers
			| ImageSize2 = 200
	| CASNo = <!-- blanked - oldvalue: 98-02-2 -->
			| ImageName2 = Ball-and-stick model
⚫	| PubChem = 7363
		⚫	|Section1={{Chembox Identifiers
	| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
			| CASNo_Ref = {{cascite|correct|CAS}}
	| ChemSpiderID = 7085
			| CASNo = 98-02-2
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| EINECS = 202-628-2
	| UNNumber = 3336		| UNII = 29W096TCPG
		⚫	| PubChem = 7363
⚫	| MeSHName = furfuryl+mercaptan
	| Beilstein = 383594		| ChemSpiderID = 7085
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| RTECS = LU2100000
	| SMILES = SCc1ccco1		| EINECS = 202-628-2
	| SMILES1 = SCC1=CC=CO1		| UNNumber = 3336
		⚫	| MeSHName = furfuryl+mercaptan
⚫	| StdInChI = 1S/C5H6OS/c7-4-5-2-1-3-6-5/h1-3,7H,4H2
			| Beilstein = 383594
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| RTECS = LU2100000
⚫	| StdInChIKey = ZFFTZDQKIXPDAF-UHFFFAOYSA-N
			| SMILES = SCc1ccco1
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| SMILES1 = SCC1=CC=CO1
		⚫	| StdInChI = 1S/C5H6OS/c7-4-5-2-1-3-6-5/h1-3,7H,4H2
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChIKey = ZFFTZDQKIXPDAF-UHFFFAOYSA-N
		⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 5		| C=5 | H=6 | S=1 | O=1
		⚫	| Appearance = Colourless liquid
	| H = 6
		⚫	| Odor = Roasted coffee, Caramel, Sulfurous, Waxy
	| S = 1
		⚫	| Density = 1.132 g cm<sup>−3</sup>
	| O = 1
		⚫	| BoilingPtK = 428
	| ExactMass = 114.013935504 g mol<sup>-1</sup>
		⚫	| VaporPressure = 531 Pa
⚫	| Appearance = Colourless liquid
⚫	| Odor = Roasted coffee, Caramel, Sulfurous, Waxy
⚫	| Density = 1.132 g cm<sup>-3</sup>
⚫	| BoilingPtK = 428
⚫	| VaporPressure = 531 Pa
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| GHSPictograms = {{GHS flame}}		| GHSPictograms = {{GHS flame}}
	| GHSSignalWord = '''WARNING'''		| GHSSignalWord = '''WARNING'''
	| HPhrases = {{H-phrases|226}}		| HPhrases = {{H-phrases|226}}
			| FlashPtC = 45
	| EUClass = {{Hazchem Xi}}
		⚫	| LD50 = 100-200 mg kg<sup>−1</sup> (mouse)
	| RPhrases = {{R10}}, {{R36/37/38}}
	| SPhrases = {{S2}}, {{S24/25}}, {{S26}}, {{S36}}
	| FlashPt = {{Convert|45|C|F}}
⚫	| LD50 = 100-200 mg kg<sup>-1</sup> (mouse)
	}}		}}
	}}		}}
	'''Furan-2-ylmethanethiol''' is an ] containing a ] 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. In fact, is a key component of the aroma of roasted coffee.		'''Furan-2-ylmethanethiol''' ('''2-Furanmethanethiol''') is an ] containing a ] 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 ] following ] infection.<ref>{{Cite medRxiv |vauthors=Parker JK, Kelly CE, Gane SB |title=Molecular Mechanism of Parosmia. |date=5 February 2021 |page=21251085 |medrxiv=10.1101/2021.02.05.21251085}}</ref><ref>{{cite web | url = https://www.theguardian.com/world/2022/may/25/scientists-identify-trigger-molecule-for-covid-related-changes-to-smell | vauthors = Devlin H | title = Scientists identify 'trigger molecule' for Covid-related changes to smell. | work = The Guardian | date = 25 May 2022 }}</ref>
			==Synthesis ==
			Furan-2-ylmethanethiol is easily prepared by reacting ] with ] in ] via an intermediate ] salt which is ] to the ] by heating with ].<ref>{{Cite journal |title=Preparation of furfuryl mercaptane | journal = Organic Syntheses | date = 1955 | volume = 35 | page = 66 | doi = 10.15227/orgsyn.035.0066 |url=http://www.orgsyn.org/demo.aspx?prep=CV4P0491}}</ref>
			]
			{{-}}
	== References ==		== References ==
	{{Reflist}}		{{Reflist}}
			{{Coffee}}
	{{Aromatic-stub}}		{{Aromatic-stub}}
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			]
	]		]
	]		]