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Nile blue

Nile blue
Names
IUPAC name
[9-(diethylamino)benzo[a]phenoxazin-5-ylidene]azanium sulfate
Other names
Nile blue A, Nile blue sulfate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.757 Edit this at Wikidata
UNII
  • InChI=1S/C20H21N3O/c1-3-23(4-2)13-9-10-17-18(11-13)24-19-12-16(21)14-7-5-6-8-15(14)20(19)22-17/h5-13H,3-4,21H2,1-2H3 checkY
    Key: WOIORDFNOALMFO-UHFFFAOYSA-N checkY
  • InChI=1/C20H21N3O/c1-3-23(4-2)13-9-10-17-18(11-13)24-19-12-16(21)14-7-5-6-8-15(14)20(19)22-17/h5-13H,3-4,21H2,1-2H3
    Key: WOIORDFNOALMFO-UHFFFAOYAF
  • N=1c3c(OC=2C=1\C=C/C(N(CC)CC)C=2)cc(c4c3cccc4)N
Properties
C20H20ClN3O
Molar mass 353.845 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Nile blue (or Nile blue A) is a stain used in biology and histology. It may be used with live or fixed cells, and imparts a blue colour to cell nuclei.

It may also be used in conjunction with fluorescence microscopy to stain for the presence of polyhydroxybutyrate granules in prokaryotic or eukaryotic cells. Boiling a solution of Nile blue with sulfuric acid produces Nile red (Nile blue oxazone).

Nile blue hydrochloride in water.
Concentrations, left to right: 1000 ppm, 100 ppm, 10 ppm, 1 ppm, 100 ppb.
Nile blue in water.
Left to right: pH 0, pH 4, pH 7, pH 10, pH 14.
Nile blue in water (lower phase) and ethyl acetate (upper phase) in daylight.
Left to right: pH 0, pH 4, pH 7, pH 10, pH 14
Nile blue in water (lower phase) and ethyl acetate (upper phase) in UV light (366 nm).
Left to right: pH 0, pH 4, pH 7, pH 10, pH 14
Nile blue (free base) in daylight (top row) and UV light (366 nm, bottom row) in different solvents.
Left to right: 1. methanol, 2. ethanol, 3. methyl-tert-butylether, 4. cyclohexane, 5. n-hexane, 6. acetone, 7. tetrahydrofuran, 8. ethyl acetate, 9. dimethyl formamide, 10. acetonitrile, 11. toluene, 12. chloroform
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