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3,5-Difluoro-4-hydroxybenzylidene imidazolinone

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3,5-Difluoro-4-hydroxybenzylidene imidazolinone or DFHBI[2] is an imidazolinone fluorophore used in various biochemical studies. The benzene ring of DFHBI can freely rotate around the single bond but when it is fixed in planar conformation, DFHBI fluoresces.[1] It is a synthetic analog of the GFP fluorophore.

3,5-Difluoro-4-hydroxybenzylidene imidazolinone
Names
IUPAC name
(5Z)-5-[(3,5-Difluoro-4-hydroxyphenyl)methylene]-3,5-dihydro-2,3-dimethyl-4H-imidazol-4-one[2]
Other names
  • DFHBI
  • 3,5-Difluoro-4-hydroxybenzylidene imidazolidinone
  • (Z)-4-(3,5-Difluoro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H10F2N2O2/c1-6-15-10(12(18)16(6)2)5-7-3-8(13)11(17)9(14)4-7/h3-5,17H,1-2H3/b10-5-
    Key: ZDDIJYXDUBFLID-YHYXMXQVSA-N
  • CC1=N/C(=C\C2=CC(=C(C(=C2)F)O)F)/C(=O)N1C
Properties
C12H10F2N2O2
Molar mass 252.221 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References

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  1. ^ a b Dou, Jiayi; Vorobieva, Anastassia A.; Sheffler, William; Doyle, Lindsey A.; Park, Hahnbeom; Bick, Matthew J.; Mao, Binchen; Foight, Glenna W.; Lee, Min Yen; Gagnon, Lauren A.; Carter, Lauren (September 2018). "De novo design of a fluorescence-activating β-barrel". Nature. 561 (7724): 485–491. Bibcode:2018Natur.561..485D. doi:10.1038/s41586-018-0509-0. ISSN 0028-0836. PMC 6275156. PMID 30209393.
  2. ^ a b "DFHBI 1241390-29-3". Sigma Aldrich. Archived from the original on 2022-01-13.


 

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