3-Bromofuran is a colorless, organic compound with the molecular formulaC4H3BrO. 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).[1] While colorless when pure, it can appear light yellow when minor impurities are present. It is usually stabilized by calcium carbonate.
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.[13] 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.[14]
^ abA. F. Shepard; Winslow, N. R.; Johnson, John R. (1930). "The simple halogen derivatives of furan". J. Am. Chem. Soc. 52 (9): 2083–2090. doi:10.1021/ja01368a057.
^Carlos Alvarez-Ibarra; Quiroga, Maria L.; Toledano, Emilio (1996). "Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran". Tetrahedron. 52 (11): 4065–4078. doi:10.1016/s0040-4020(96)00069-5.
^Guenter Fechtel, "Preparation of furan and cyclopentadiene derivatives as biocides and drug intermediates" East Ger. Patent 246,107 (1987)
^Susan E. Hagen; Domagla, John; Gajda, Christopher (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. 44 (14): 2319–2332. doi:10.1021/jm0003844. PMID11428926.
^Qun Dang; Brown, Brian S.; Liu, Yan (2009). "Fructose-1,6-bisphosphatase Inhibitors. 1. Purine Phosphonic Acids as Novel AMP Mimics". Journal of Medicinal Chemistry. 52 (14): 2880–2898. doi:10.1021/jm900078f. PMID19348494.
^Zhi-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.
^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.
^Motoko Oshida; Ono, Misaki; Nakazaki, Atsuo (2010). "Total synthesis of (+)-cacospongionolide B". Heterocycles. 80 (1): 313–328. doi:10.3987/com-09-s(s)17 (inactive 2024-02-17).{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link)
^Peter Weyerstahl; Schenk, Anja; Marschall, Helga (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. 6 (10): 1849–1853. doi:10.1002/jlac.1995199510259.
^Daniel J. Jansen; Shenvi, Ryan A. (2013). "Synthesis of (−)-Neothiobinupharidine". Journal of the American Chemical Society. 135 (4): 1209–1212. doi:10.1021/ja310778t. PMID23298203.
