2-Furoyl chloride

2-Furoyl chloride
Names
Preferred IUPAC name
Furan-2-carbonyl chloride
Other names
2-Furancarbonyl chloride
2-Furancarboxylic acid chloride
2-Furanoyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.658
EC Number
  • 208-422-9
UNII
  • InChI=1S/C5H3ClO2/c6-5(7)4-2-1-3-8-4/h1-3H
    Key: OFTKFKYVSBNYEC-UHFFFAOYSA-N
  • InChI=1/C5H3ClO2/c6-5(7)4-2-1-3-8-4/h1-3H
    Key: OFTKFKYVSBNYEC-UHFFFAOYAN
  • C1=COC(=C1)C(=O)Cl
Properties
C5H3ClO2
Molar mass 130.53 g·mol−1
Appearance liquid
Density 1.3227 g/mL @ 20 °C
Melting point −2 °C (28 °F; 271 K)
Boiling point 173 °C (343 °F; 446 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Furoyl chloride is an acyl chloride of furan. It takes the form of a corrosive liquid, which is more irritating to the eyes than benzoyl chloride.[1] 2-Furoyl chloride is a useful pharmaceutical intermediate and is used in the synthesis of mometasone furoate, an antiinflammatory prodrug used in the treatment of skin disorders, hay fever and asthma.[2]

Synthesis

2-Furoyl chloride was prepared in 1924 by Gelissen by refluxing 2-furoic acid in excess thionyl chloride on a water bath.[1]

Applications

2-Furoyl chloride has no major applications but it has been used as a chemical intermediate in the synthesis of various pharmaceuticals; examples include mometasone furoate,[2] fluticasone furoate,[3] diloxanide furoate,[4] Ceftiofur (Excenel),[5] mirfentanil,[6] quinfamide,[7] and diclofurime.[8]

See also

References

  1. ^ a b H. Gelissen; van Roon, J. D. (1924). "Furfuroyl peroxide". Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. 43: 59–66.
  2. ^ a b William Heggie, "Process for the preparation of mometasone furoate", US Patent 6,177,560 B1(2001)
  3. ^ Dingjun Chu, "Method for preparation of Fluticasone furoate", CN 102558273 A 20120711 (2012)
  4. ^ Wenli Zheng; Xue, Feiqun (2006). "Synthesis of diloxanide furoate". Zhongguo Yiyao Gongye Zazhi. 37 (2): 77–78.
  5. ^ Xuke Zhang, "Method for preparation of Ceftiofur", CN Patent 101,108,855 A (2008)
  6. ^ Jerome R. Bagley; Wynn, Richard; Rudo, Frieda; Doorley, Brian; Spencer, Kenneth; Spaulding, Theodore (1989). "New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry. 32 (3): 663–71. doi:10.1021/jm00123a028. PMID 2563773.
  7. ^ Bailey, Denis M.; Mount, Eldridge M.; Siggins, James; Carlson, John A.; Yarinsky, Allen; Slighter, Ralph G. (1979). "1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents". Journal of Medicinal Chemistry. 22 (5): 599–601. doi:10.1021/jm00191a031. ISSN 0022-2623. PMID 458814.
  8. ^ DE2449205 idem Germaine Thuillier, Jacqueline Laforest, Pierre Bessin, U.S. patent 4,029,808 (1977 to C.E.R.P.H.A. A French Society Organised Under The Laws Of France).
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