| Revision as of 10:24, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473449942 of page 3-Bromofuran for the Chem/Drugbox validation project (updated: 'CASNo'). |
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{{Technical|date=January 2023|article|small=right}}{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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| verifiedrevid = 477344600 |
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| ImageFile = bromofuran.svg |
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| ImageFile = bromofuran.svg |
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| ImageSize = 120px |
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| ImageSize = 120px |
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| IUPACName = 3-Bromofuran |
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| PIN = 3-Bromofuran |
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| OtherNames = 3-Furyl bromide; ''beta''-Bromofuran |
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| OtherNames = 3-Furyl bromide; β-Bromofuran |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 22037-28-1 --> |
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| PubChem = 89164 |
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| CASNo = 22037-28-1 |
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| ChemSpiderID = 80460 |
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| PubChem = 89164 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = Brc1ccoc1 |
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| ChemSpiderID = 80460 |
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| InChI = 1/C4H3BrO/c5-4-1-2-6-3-4/h1-3H |
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| SMILES = Brc1ccoc1 |
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| InChIKey = LXWLEQZDXOQZGW-UHFFFAOYAM |
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| StdInChI = 1S/C4H3BrO/c5-4-1-2-6-3-4/h1-3H |
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| InChI = 1/C4H3BrO/c5-4-1-2-6-3-4/h1-3H |
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| StdInChIKey = LXWLEQZDXOQZGW-UHFFFAOYSA-N |
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| InChIKey = LXWLEQZDXOQZGW-UHFFFAOYAM |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H3BrO/c5-4-1-2-6-3-4/h1-3H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LXWLEQZDXOQZGW-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 4 | H = 3 | Br = 1 | O = 1 |
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| C=4 | H=3 | Br=1 | O=1 |
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| Appearance = |
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| Appearance = |
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| Density = 1.6606 @20 °C |
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| Density = 1.6606 @20 °C |
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| MeltingPt = |
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| MeltingPt = |
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| BoilingPt = 102.5-102.6 °C |
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| BoilingPtC = 102.5 to 102.6 |
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| Section3 = {{Chembox Hazards |
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'''3-Bromofuran''' is a colorless, organic compound with the ] '''C<sub>4</sub>H<sub>3</sub>BrO'''. A versatile intermediate product for synthesizing more complex compounds, it used in the syntheses of a variety of economically important drugs. |
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A liquid at room temperature, it has a similar boiling point to water (102.5-102.6 °C), but with a significantly higher density (1.6606 g/cm3 at 20 °C).<ref name="Shepard" /> While colorless when pure, it can appear light yellow when minor impurities are present. It is usually stabilized by calcium carbonate. |
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== Synthesis == |
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3-Bromofuran was obtained in minor amounts in 1887 as a ] in a reaction of ] with ].<ref>{{cite journal |title=none| author = Conzoneri | author2 = Oliveri | journal = Gazz. Chim. Ital.| volume = 17 | pages = 43 | year = 1887}}</ref> Four decades later, it was prepared deliberately and in higher yield.<ref name="Shepard">{{cite journal | author = A. F. Shepard | title = The simple halogen derivatives of furan | journal = J. Am. Chem. Soc. | volume = 52 | pages = 2083–2090 | year = 1930 |last2 = Winslow | first2 = N. R. | last3 = Johnson | first3 = John R. | issue = 9 | doi=10.1021/ja01368a057}}</ref> 3-bromofuran has since also been prepared from ] via ] with ]{{Clarify|date=January 2023|reason=There is more than one compound with the same name}} in good yield.<ref>{{cite journal | author = Carlos Alvarez-Ibarra | title = Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran. | journal = Tetrahedron | volume = 52 | pages = 4065–4078 | year = 1996 |last2 = Quiroga | first2 = Maria L. | last3 = Toledano | first3 = Emilio | issue = 11 | doi=10.1016/s0040-4020(96)00069-5}}</ref> A synthesis of 3-bromofuran is due to Fechtel<ref>Guenter Fechtel, "Preparation of furan and cyclopentadiene derivatives as biocides and drug intermediates" East Ger. Patent 246,107 (1987)</ref> who prepared this compound via a ]-]-] sequence. |
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== Applications == |
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3-Bromofuran is a useful starting material for 3-substituted ]s, a structural motif widespread in ] agents,<ref>{{cite journal | author = Han-Zhong Zhang | title = Discovery and Structure-Activity Relationship of 3-Aryl-5-aryl-1,2,4-oxadiazoles as a New Series of Apoptosis Inducers and Potential Anticancer Agents. | journal = Journal of Medicinal Chemistry | volume = 48 | pages = 5215–5223| year = 2005 |last2 = Kasibhatla | first2 = Shailaja | last3 = Kuemmerle | first3 = Jared | issue = 16 | doi=10.1021/jm050292k| pmid = 16078840 | url = https://figshare.com/articles/journal_contribution/3273325 }}</ref> ] drugs,<ref>{{cite journal | author = Susan E. Hagen | title = 4-Hydroxy-5,6-dihydropyrones as inhibitors of HIV protease: the effect of heterocyclic substituents at C-6 on antiviral potency and pharmacokinetic parameters | journal = Journal of Medicinal Chemistry | volume = 44 | pages = 2319–2332 | year = 2001 |last2 = Domagla | first2 = John | last3 = Gajda | first3 = Christopher | issue = 14 | doi=10.1021/jm0003844| pmid = 11428926 }}</ref> ] treatments,<ref>{{cite journal | author = Qun Dang | title = Fructose-1,6-bisphosphatase Inhibitors. 1. Purine Phosphonic Acids as Novel AMP Mimics | journal = Journal of Medicinal Chemistry | volume = 52 | pages = 2880–2898| year = 2009 |last2 = Brown | first2 = Brian S. | last3 = Liu | first3 = Yan | issue = 14 | doi=10.1021/jm900078f | pmid=19348494}}</ref> drugs for ]<ref>Zhi-Cai Shi, et al., " Preparation of 4--(S)-phenylalanine derivative tryptophan hydroxylase inhibitors for treating osteoporosis |
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", US PCT Int. Appl. (2010), WO 2010065333 A1 20100610.</ref> and experimental drugs for ].<ref>Zhi-Cai Shi, et al., " Preparation of a (((1,2,4-oxadiazolyl)phenyl)morpholino)pyrimidin-4-one compound as a therapeutic tau protein kinase inhibitor ", PCT Int. Appl. (2009), WO 2009035162 A1 20090319.</ref> For example, the ] of ], a ] with anti-inflammatory properties,<ref>{{cite journal | author = Inmaculada Posadas | title = Cacospongionolide B suppresses the expression of inflammatory enzymes and tumour necrosis factor-α by inhibiting nuclear factor-κB activation | journal = Br J Pharmacol| volume = 138 | pages = 1571–1579 | year = 2003 |last2 = De Rosa | first2 = Salvatore | last3 = Terencio | first3 = M Carmen | issue = 8 | doi=10.1038/sj.bjp.0705189| pmid = 12721113 | pmc = 1573800 }}</ref> has been accomplished using 3-bromofuran as a starting compound.<ref>{{cite journal | author = Motoko Oshida | title = Total synthesis of (+)-cacospongionolide B | journal = Heterocycles | volume = 80 | pages = 313–328 | year = 2010 |last2 = Ono | first2 = Misaki | last3 = Nakazaki | first3 = Atsuo | issue = 1 | doi=10.3987/com-09-s(s)17| doi-access = free }}</ref> It was also used to synthesize ], a constituent chemical of the odor of the rose and an insect sex attractant. 3-bromofuran was reacted with ] and ], followed by reaction at with ] and ].<ref>{{cite journal | author = Peter Weyerstahl | title = Structure-odor correlation. Part XXI. Olfactory properties and convenient synthesis of furans and thiophenes related to rosefuran and perillene and their isomers | journal = Liebigs Annalen | volume = 6 | pages = 1849–1853| year = 1995 |last2 = Schenk | first2 = Anja | last3 = Marschall | first3 = Helga | issue = 10 | doi=10.1002/jlac.1995199510259}}</ref> |
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The total synthesis of (−)-], a bioactive alkaloid isolated from ] (the small ]) was accomplished in eight steps employing two moles of 3-bromofuran.<ref>{{cite journal | author = Daniel J. Jansen| title = Synthesis of (−)-Neothiobinupharidine| journal = Journal of the American Chemical Society| volume = 135 | issue = 4| pages = 1209–1212| year = 2013| last2 = Shenvi| first2 = Ryan A.| doi=10.1021/ja310778t| pmid=23298203}}</ref> Similarly, one of the steps of the total synthesis of ], the primary hallucinogenic compound in ], a Mexican plant used by ], used 3-bromofuran as a reactant.<ref>{{cite journal | author = Hisahiro Hagiwara| title = Second-generation synthesis of salvinorin A| journal = Tetrahedron| volume = 65 | issue = 25| pages = 4820–4825| year = 2005| last2 = Suka| first2 = Yuhki| last3 = Nojima| first3 = Takashi| last4 = Suzuki| first4 = Toshio| doi=10.1016/j.tet.2009.04.053}}</ref> |
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== References == |
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{{Reflist}} |
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{{DEFAULTSORT:Bromofuran, 3-}} |
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] |
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] |