3-Bromofuran

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title: "3-Bromofuran" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["3-furyl-compounds", "bromoarenes"] topic_path: "general/3-furyl-compounds" source: "https://en.wikipedia.org/wiki/3-Bromofuran" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477344600 | ImageFile = bromofuran.svg | ImageSize = 120px | PIN = 3-Bromofuran | OtherNames = 3-Furyl bromide; β-Bromofuran |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 22037-28-1 | PubChem = 89164 | ChemSpiderID_Ref = | ChemSpiderID = 80460 | SMILES = Brc1ccoc1 | InChI = 1/C4H3BrO/c5-4-1-2-6-3-4/h1-3H | InChIKey = LXWLEQZDXOQZGW-UHFFFAOYAM | StdInChI_Ref = | StdInChI = 1S/C4H3BrO/c5-4-1-2-6-3-4/h1-3H | StdInChIKey_Ref = | StdInChIKey = LXWLEQZDXOQZGW-UHFFFAOYSA-N |Section2={{Chembox Properties | C=4 | H=3 | Br=1 | O=1 | Appearance = | Density = 1.6606 @20 °C | MeltingPt = | BoilingPtC = 102.5 to 102.6 | BoilingPt_notes = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

3-Bromofuran is a colorless, organic compound with the molecular formula C4H3BrO. A versatile intermediate product for synthesizing more complex compounds, it used in the syntheses of a variety of economically important drugs.

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). While colorless when pure, it can appear light yellow when minor impurities are present. It is usually stabilized by calcium carbonate.

Synthesis

3-Bromofuran was obtained in minor amounts in 1887 as a by-product in a reaction of 3-bromofuroic acid with calcium hydroxide. Four decades later, it was prepared deliberately and in higher yield. 3-bromofuran has since also been prepared from 3,4-dibromofuran via ortho-metalation with butyllithium in good yield. A synthesis of 3-bromofuran is due to Fechtel who prepared this compound via a Diels Alder-bromination-reverse Diels Alder sequence.

Applications

3-Bromofuran is a useful starting material for 3-substituted furans, a structural motif widespread in chemotherapy agents, HIV drugs, type 2 diabetes treatments, drugs for osteoporosisZhi-Cai Shi, et al., " Preparation of 4-[6-(2,2,2-trifluoro-1-phenylethoxy)pyrimidin-4-yl]-(S)-phenylalanine derivative tryptophan hydroxylase inhibitors for treating osteoporosis ", US PCT Int. Appl. (2010), WO 2010065333 A1 20100610. and experimental drugs for Alzheimer's disease. For example, the total synthesis of (+)Cacospongionolide B, a sesterterpene with anti-inflammatory properties, has been accomplished using 3-bromofuran as a starting compound. It was also used to synthesize Rosefuran, a constituent chemical of the odor of the rose and an insect sex attractant. 3-bromofuran was reacted with 3,3-dimethylallyl bromide and lithium diisopropylamide, followed by reaction at with iodomethane and N-butyllithium.

The total synthesis of (−)-neothiobinupharidine, a bioactive alkaloid isolated from Nuphar pumila (the small yellow pond-lily) was accomplished in eight steps employing two moles of 3-bromofuran. Similarly, one of the steps of the total synthesis of Salvinorin A, the primary hallucinogenic compound in Salvia divinorum, a Mexican plant used by Mazatec shamans, used 3-bromofuran as a reactant.

References

References

  1. Conzoneri. (1887). "none".
  2. A. F. Shepard. (1930). "The simple halogen derivatives of furan". J. Am. Chem. Soc..
  3. Carlos Alvarez-Ibarra. (1996). "Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran.". Tetrahedron.
  4. Guenter Fechtel, "Preparation of furan and cyclopentadiene derivatives as biocides and drug intermediates" East Ger. Patent 246,107 (1987)
  5. Han-Zhong Zhang. (2005). "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 of Medicinal Chemistry.
  6. Susan E. Hagen. (2001). "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 of Medicinal Chemistry.
  7. Qun Dang. (2009). "Fructose-1,6-bisphosphatase Inhibitors. 1. Purine Phosphonic Acids as Novel AMP Mimics". Journal of Medicinal Chemistry.
  8. 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.
  9. Inmaculada Posadas. (2003). "Cacospongionolide B suppresses the expression of inflammatory enzymes and tumour necrosis factor-α by inhibiting nuclear factor-κB activation". Br J Pharmacol.
  10. Motoko Oshida. (2010). "Total synthesis of (+)-cacospongionolide B". Heterocycles.
  11. Peter Weyerstahl. (1995). "Structure-odor correlation. Part XXI. Olfactory properties and convenient synthesis of furans and thiophenes related to rosefuran and perillene and their isomers". Liebigs Annalen.
  12. Daniel J. Jansen. (2013). "Synthesis of (−)-Neothiobinupharidine". Journal of the American Chemical Society.
  13. Hisahiro Hagiwara. (2005). "Second-generation synthesis of salvinorin A". Tetrahedron.

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3-furyl-compoundsbromoarenes