Nile Red
- CAS No.
- 7385-67-3
- Chemical Name:
- Nile Red
- Synonyms
- NILE BLUE A OXAZONE;Fluorescent Spectral Standard E, certified;9-(DIETHYLAMINO)-5H-BENZO[A]PHENOXAZIN-5-ONE;nile;NILE RED;nilereddye;Phenoxazone;Oxazine O-17M;Nile Red ,99%;Phenoxazone 9
- CBNumber:
- CB0273873
- Molecular Formula:
- C20H18N2O2
- Molecular Weight:
- 318.37
- MOL File:
- 7385-67-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/1/18 11:15:07
| 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 |
| 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
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280-P301+P312-P302+P352-P305+P351+P338 | |||||||||
| Safety Statements | 24/25 | |||||||||
| WGK Germany | 3 | |||||||||
| F | 8-10 | |||||||||
| HS Code | 29349990 | |||||||||
| NFPA 704 |
|
Nile Red price More Price(17)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | N3013 | Nile Red Technical grade | 7385-67-3 | 100MG | ₹11620 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | N3013 | Nile Red Technical grade | 7385-67-3 | 1G | ₹61671.6 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 72485 | Nile Red for microscopy | 7385-67-3 | 100MG | ₹15540 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 72485 | Nile Red for microscopy | 7385-67-3 | 1G | ₹60162 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 19123 | Nile Red BioReagent, suitable for fluorescence, ≥97.0% (HPLC) | 7385-67-3 | 10MG | ₹11988 | 2022-06-14 | Buy |
Nile Red Chemical Properties,Uses,Production
Description
Nile red is a dye based on the benzo[a]phenoxazine core. Nile Red (9-diethylbenzo[a]phenoxazin-5- one) stands out as electrically neutral and water-insoluble since it features a carbonyl group at the 5-position that readily accepts the electron density. This makes it a strong push?pull chromophore, which underlies its distinct solvatochromicity and ability to indicate, e.g., cellular events in live-cell imaging. In addition, Nile Red’s inherent lipophilicity, near-infrared (NIR) emission, large Stokes shift, two-photon absorptivity (2PA), and low background fluorescence (as the luminosity is quenched in aqueous (aq) media) render it a near-ideal histochemical stain for studying membranes and lipid droplets in cells. The increase of its exquisite solvent sensitivity and steep emission in hydrophobic environments has also been employed in various forms of stochastic super-resolution localization microscopy[1].
Chemical Properties
solid
Uses
Nile red is a lipophilic stain. Nile red stains intracellular lipid droplets. Nile red is also intensely fluorescent, with a strong yellow-gold emission if included into a lipid-rich environment.
Definition
ChEBI: An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.
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].
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 Preparation Products And Raw materials
Raw materials
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| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Central Drug House(P) Ltd. | 91-11-49404040 | New Delhi, India | 6160 | 58 | Inquiry |
| GSP Chemical Industries (Esjay Chemicals) | 91-2525-661040 | Maharashtra, India | 68 | 58 | Inquiry |
| Kalash Intermediates | 91-9426001352 | Gujarat, India | 39 | 58 | Inquiry |
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