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Revision as of 14:14, 20 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|erro← Previous edit		Latest revision as of 01:04, 19 December 2024 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,032 editsmNo edit summary
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 401596647		| verifiedrevid = 403351202
	| ImageFile = 2-Aminothiazole.png		| ImageFile = 2-Aminothiazole.svg
	| ImageSize = 100px		| ImageSize = 150px
			| ImageAlt = Skeletal formula of aminothiazole
⚫	| IUPACName = 1,3-thiazol-2-amine
			| ImageFile1 = 2-Aminothiazole-3D-spacefill.png
			| ImageSize1 = 140
			| ImageAlt1 = Space-filling model of the aminothiazole molecule
		⚫	| PIN = 1,3-Thiazol-2-amine
	| OtherNames = 2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole		| OtherNames = 2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| UNII_Ref = {{fdacite|correct|FDA}}		| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| CASNo = 96-50-4
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID = 2070
		⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 40782
		⚫	| ChEMBL_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEMBL = 344760
			| EINECS = 202-511-6
		⚫	| PubChem = 2155
			| KEGG_Ref = {{keggcite|correct|kegg}}
		⚫	| KEGG = D02479
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 5K8WKN668K		| UNII = 5K8WKN668K
	| InChI = 1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)		| InChI = 1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = RAIPHJJURHTUIC-UHFFFAOYSA-N		| StdInChIKey = RAIPHJJURHTUIC-UHFFFAOYSA-N
		⚫	| SMILES = c1csc(n1)N
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| CASNo = 96-50-4
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID = 2070
⚫	| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫	| ChEMBL = 344760
⚫	| PubChem = 2155
⚫	| KEGG = D02479
⚫	| SMILES = c1csc(n1)N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	|C=3|H=4|N=2|S=1		| C=3 | H=4 | N=2 | S=1
	| Appearance = light yellow crystals		| Appearance = Light yellow crystals
	| Density =		| Density =
	| MeltingPt = 86 - 89 °C		| MeltingPtC = 86 to 89
			| MeltingPt_notes =
	| BoilingPt = 117 °C (20 hPa)
			| BoilingPtC = 117
⚫	| Solubility = 100 g/l (20 °C)
			| BoilingPt_notes = (20 hPa)
⚫	}}
		⚫	| Solubility = 100 g/L (20 °C)
⚫	| Section3 = {{Chembox Hazards
			| MagSus = -56.0·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫	| MainHazards =
⚫	| FlashPt =
	| Autoignition = 600 °C
⚫	| NFPA-H = 2
⚫	| NFPA-F = 0
⚫	| NFPA-R = 0
⚫	| NFPA-O =
	}}		}}
		⚫	|Section3={{Chembox Hazards
		⚫	| MainHazards =
		⚫	| FlashPt =
			| AutoignitionPtC = 600
			| AutoignitionPt_notes =
		⚫	| NFPA-H = 2
		⚫	| NFPA-F = 0
		⚫	| NFPA-R = 0
		⚫	| NFPA-S =
			| GHS_ref=<ref>{{cite web |title=2-Aminothiazole |url=https://pubchem.ncbi.nlm.nih.gov/compound/2155#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2022 |language=en}}</ref>
			| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|302|319}}
			| PPhrases = {{P-phrases|264|264+265|270|280|301+317|305+351+338|330|337+317|501}}
		⚫	}}
	}}		}}
	'''2-Aminothiazole''' is a heterocyclic ] with odor similar to ], soluble in water, alcohol and ether. It is a beginning point for synthesis of many compounds including sulfur drugs, biocides, fungicides, dyes and chemical reaction accelerators. 2-Aminothiazole can be used as a ] inhibitor in the treatment of ] and it has antibacterial activity.		'''2-Aminothiazole''' is a heterocyclic ] featuring a ] core. It can also be considered a cyclic isothiourea. It possesses an odor similar to ] and is soluble in water, alcohols and diethyl ether. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a ] ("sulfa drugs"). 2-Aminothiazole can be used as a ] inhibitor in the treatment of ].<ref>{{cite book |doi=10.1002/14356007.a27_039 |chapter=Thyrotherapeutic Agents |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2000 |last1=Dahlmanns |first1=Simone M. |last2=Müller-Gärtner |first2=Hans-Wilhelm |isbn=9783527303854 }}</ref>
			2-Aminothiazole is prepared from ], ], and ].<ref>{{cite journal |doi=10.1002/hlca.19550380529 |title=Zur Synthese von 2-Amino-thiazolderivaten |date=1955 |last1=Erlenmeyer |first1=H. |last2=Herzfeld |first2=L. |last3=Prijs |first3=B. |journal=Helvetica Chimica Acta |volume=38 |issue=5 |pages=1291–1294 }}</ref>
	== External links ==
	*
	*
			==2-Aminothiazoles==
⚫	]
			Like the parent, 2-aminothiazoles are often produced by the condensation of ] and an ].<ref>{{OrgSynth | title = 2-Amino-4-methylthiazole | author1 = J. R. Byers|author2= J. B. Dickey| year = 1939| volume = 19 | page = 10 | doi = 10.15227/orgsyn.019.0010}}</ref><ref>{{cite journal |doi=10.15227/orgsyn.091.0185 |title=Synthesis of 4,5-Disubstituted 2-Aminothiazoles from α,β-Unsaturated Ketones: Preparation of 5-Benzyl-4-methyl-2-aminothiazolium Hydrochloride Salt |date=2014 |last1=Gómez |first1=Antonio Bermejo |first2=Nanna|last2=Ahlsten |first3=Ana E.|last3=Platero-Prats |first4=Belén |last4=Martín-Matutejournal=Organic Syntheses |journal=Organic Syntheses |volume=91 |pages=185–200 |doi-access=free }}</ref><ref name=Mateo>{{cite journal | title = On the Cycloaddition of 2-Aminothiazoles and Dimethyl Acetylenedicarboxylate. Experimental and Computational Evidence of a Thermal Disrotatory Ring Opening of Fused Cyclobutenes |author1=Alajarín, M. |author2=Cabrera, J. |author3=Pastor, A. |author4=Sánchez-Andrada, P. |author5=Bautista, D. | journal = ] | year = 2006 | volume = 71 | issue = 14 | pages = 5328–5339 | doi = 10.1021/jo060664c | pmid = 16808523 }}</ref>
	]
			:]{{clear left}}
	{{Amine-stub}}
	{{heterocyclic-stub}}
			In an adaptation of the ], a 2-acylamino-ketone reacts with ].
	]
	]
			==Applications==
			Synthetic aminothiazoles - compounds containing the parent 2-aminothiazole as a subunit - are used in ]. Some examples are ], ], ], ], ], ], ], ], ], ], ], ], ], ], and ].<ref>{{cite journal |doi=10.1016/j.ejmech.2015.12.022 |title=Recent Developments of 2-Aminothiazoles in Medicinal Chemistry |date=2016 |last1=Das |first1=Debasis |last2=Sikdar |first2=Papiya |last3=Bairagi |first3=Moumita |journal=European Journal of Medicinal Chemistry |volume=109 |pages=89–98 |pmid=26771245 }}</ref><ref>{{cite journal |doi=10.1016/j.ejmech.2020.112953 |title=2-Aminothiazole: A privileged scaffold for the discovery of anti-cancer agents |date=2021 |last1=Wan |first1=Yichao |last2=Long |first2=Jiabing |last3=Gao |first3=Han |last4=Tang |first4=Zilong |journal=European Journal of Medicinal Chemistry |volume=210 |pmid=33148490 |s2cid=226258989 }}</ref>
			==References==
			{{reflist}}
			{{DEFAULTSORT:Aminothiazole}}
		⚫	]
			]