Nile Red Chemical Properties

Melting point:

203-205 °C(lit.)

Boiling point:

457.53°C (rough estimate)

Density 

1.1871 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

2-8°C

solubility 

methanol: soluble1mg/mL

form 

Powder

pka

4.08±0.20(Predicted)

color 

Dark red to maroon

Appearance

Green to Dark Green Solid

λmax

553 nm

BRN 

279110

Stability:

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 DataBase Reference

7385-67-3(CAS DataBase Reference)

EPA Substance Registry System

5H-Benzo[a]phenoxazin-5-one, 9-(diethylamino)- (7385-67-3)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

8-10

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Nile Red Usage And Synthesis

Description

Nile Red is an aphotostable and lipophilic stain for intracellular lipids and hydrophobic domains of proteins and also for staining of lysosomal phospholipid inclusions.

Uses

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.

Application

Used as a polarity-sensitive fluorescent probe of lipids and proteins.

General Description

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.

Synthesis

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].

storage

Room temperature

References

[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.

Nile Red (7385-67-3)Related Product Information

• m-Anisidine
• 3-Diethylaminophenol
• 3-Dimethylaminophenol
• o-Phenetidine
• 3-ETHYLAMINOPHENOL
• INDOPHENOL BLUE
• N,N-Diethyl-1,4-phenylenediamine
• Nile Red
• 3-Dimethylaminoanisole
• Rifalazil
• 4-METHOXY-3-BUTEN-2-ONE
• N-Benzylideneaniline
• 3-METHOXY-N-METHYLANILINE
• ETH-(E)-YLIDENE-PHENYL-AMINE
• 3-ETHOXY-N,N-DIETHYLANILINE
• 2-PHENYLETHYL PHENYL ETHER
• Benzoxazine
• 9-DIETHYLAMINO-2-HYDROXY-5H-BENZ(A)-