9-(Diethylamino)benzo[a]phenoxazin-5(5H)-on

Bezeichnung:9-(Diethylamino)benzo[a]phenoxazin-5(5H)-on

Englisch Name:Nile Red

CBNumberCB0273873

SummenformelC20H18N2O2

Molgewicht318.37

Synonyma

9-(Diethylamino)benzo[a]phenoxazin-5(5H)-on

9-(Diethylamino)benzo[a]phenoxazin-5(5H)-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	203-205 °C(lit.)
Siedepunkt	457.53°C (rough estimate)
Dichte	1.1871 (rough estimate)
Brechungsindex	1.5700 (estimate)
storage temp.	2-8°C
Löslichkeit	methanol: soluble1mg/mL
pka	4.08±0.20(Predicted)
Aggregatzustand	Powder
Farbe	Dark red to maroon
BRN	279110
Stabilität	Stable. Incompatible with strong oxidizing agents.
InChI	InChI=1S/C20H18N2O2/c1-3-22(4-2)13-9-10-16-18(11-13)24-19-12-17(23)14-7-5-6-8-15(14)20(19)21-16/h5-12H,3-4H2,1-2H3
InChIKey	VOFUROIFQGPCGE-UHFFFAOYSA-N
SMILES	C12=CC=CC=C1C(=O)C=C1C2=NC2=C(C=C(N(CC)CC)C=C2)O1
CAS Datenbank	7385-67-3(CAS DataBase Reference)
EPA chemische Informationen	5H-Benzo[a]phenoxazin-5-one, 9-(diethylamino)- (7385-67-3)

Sicherheit

Gefahreninformationscode (GHS)

S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Verwenden
Nile red is a lipophilic stain. It stains intracellular lipid droplets. Nile red is also intensely fluorescent, with a strong yellow-gold emission if included into a lipid-rich environment.
Definition
Nile Red is an organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.
Allgemeine Beschreibung
Nile Red is an uncharged hydrophobic molecule and a benzophenoxazone dye. It functions as a fluorescent probe for intracellular lipids and hydrophobic domains of proteins. This dye is fluorescent in all organic solvents. Its fluorescence colors range from golden yellow to deep red.
Synthese
Using the 1,3-Naphthalenediol Approach to synthsis Nile red. To a solution of 1,3-naphthalenediol (0.50 g, 3.12 mmol) in anhydrous DMF (25 mL) was added 4-nitroso-N,N-diethylaniline (0.56 g, 3.12 mmol). This reaction mixture was stirred at 80 °C (DrySyn heating block) for 16 h and concentrated under reduced pressure. The crude product was purified by flash chromatography (0?50% EtOAc in hexanes) to obtain Nile Red, which crystallized from hexanes in green crystals (0.80 g, 2.50 mmol). Yield: 80%[1].
Lager
Room temperature
Einzelnachweise
[1] Mick Hornum*. “Substituted 9-Diethylaminobenzo[a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties.” The Journal of Organic Chemistry 86 2 (2020): 1471–1488.