22037-28-1 Usage
Chemical Properties
3-Bromofuran is a colorless to light yellow liquid having a boiling point similar to that of water (102.5-102.6 °C), but with density significantly higher (1.6606 g/cm3 at 20 °C).It is colorless when it is pure; however, the color can be light yellow when minor impurities are present. It is usaually stablized by calcium carbonate. It was used in the preparation of 2-substituted 3-furfurals. It was also used in the synthesis of 5,6-dehydronorcantharidins. 3-bromofuran is one of the volatile metabolites discussed in studies for detecting and discriminating diseases of onion.
Uses
3-Bromofuran is heterocyclic building block used in organic synthesis. 3-Bromofuran is one of the volatile metabolites discussed in studies for detecting and discriminating diseases of onion.
Synthesis
3-Bromofuran was obtained in minor amounts in 1887 as a byproduct in a reaction of 3-bromofuroic acid with calcium hydroxide. About four decades later this compound was prepared deliberately and in higher yield. 3-bromofuran has been prepared from 3,4-dibromofuran via ortho-metalation with butyl lithium in good yield. An elegant synthesis of 3-bromofuran is due to Fechtel who prepared this compound via a Diels Alder-bromination-reverse Diels Alder sequence.
Purification Methods
Purify 3-bromofuran by two steam distillations and dry it over fresh CaO. It can be dried over Na metal (no obvious reaction) and fractionated. It is not very soluble in H2O but is soluble in organic solvents. When freshly distilled, it is a clear oil, but darkens on standing and eventually resinifies. It can be stored for long periods by covering the oil with an alkaline solution of hydroquinone and is redistilled when required. It forms a characteristic maleic anhydride adduct, m 131.5-132o. [Shepard et al. J Am Chem Soc 52 2083 1930, Huhes & Johnson J Am Chem Soc 53 737 1931, adduct: van Campen & Johnson J Am Chem Soc 55 430 1933, Beilstein 17/1 V 295.]
Check Digit Verification of cas no
The CAS Registry Mumber 22037-28-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,0,3 and 7 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 22037-28:
(7*2)+(6*2)+(5*0)+(4*3)+(3*7)+(2*2)+(1*8)=71
71 % 10 = 1
So 22037-28-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H3BrO/c5-4-1-2-6-3-4/h1-3H
22037-28-1Relevant articles and documents
Synthesis and characterization of regiorandom and regioregular poly(3-octylfuran)
Politis,Nemes,Curtis
, p. 2537 - 2547 (2001)
Poly(3-octylfuran) has been synthesized with three regioregularities: P3OF-95, P3OF-75 and P3OF-50, where the number signifies the percentage HT content. The 95% HT material is highly crystalline with a structure similar to that of HT-poly(3-octylthiophene), P3OT. The lamellar spacing is 22.1 A and the π-stacking distance is 3.81 A. UV-vis spectroscopy reveals that P3OF-95 is aggregated in CHCl3 solution, and solid films of P3OF-95, but not P3OF-75 or -50, show Davydov and exciton band splitting due to the interactions of the π-systems in the stacked morphology. An estimate of the Davydov splitting is 0.15 eV (1200 cm-1). P3OF is reversibly oxidized at 0.32 V vs ferrocene/ferrocenium, but increasing the potential to 1.15 V leads to irreversible oxidation. Films of P3OF may be p-doped with iodine vapor. Doped P3OF-95 and -75 films have electrical conductivities of 10-2 and 10-7 S/cm, respectively. The UV-vis-NIR spectra of the iodine-doped films are interpreted in terms of molecular-like transitions involving the LUMO, HOMO, HOMO-1, and transitions across a Peierls distortion-induced gap in the intermolecular conduction band that is formed by the overlap of the π-systems of the stacked partially oxidized chains. The conduction band gap estimated for P3OF-95 is 0.34 eV, and that for P3OF-75 is 0.9 eV. The P3OF samples are thermally stable in N2 atmosphere to between 275°C (P3OF-50) and 380°C (P3OF-95), but suffer thermal oxidation above 150°C or light-induced oxidation at room temperature.
An improved synthesis of 3-substituted furans from substituted butene- 1,4-diols
Kraus, George A.,Wang, Xuemei
, p. 1093 - 1096 (2007/10/03)
A two-phase mixture of water and hexanes improves the yields of furans produced by the oxidation of butene-1,4-diols.
