Nile red

Base Information

• Chemical Name: Nile red
• CAS No.: 7385-67-3
• Deprecated CAS: 72506-41-3
• Molecular Formula: C20H18 N2 O2
• Molecular Weight: 318.375
• Hs Code.: 2933990090
• European Community (EC) Number: 230-966-0
• UNII: P476F1L81G
• DSSTox Substance ID: DTXSID7064653
• Nikkaji Number: J278.800D
• Wikipedia: Nile_red
• Wikidata: Q910572
• ChEMBL ID: CHEMBL144472
• Mol file: 7385-67-3.mol

Synonyms:9-diethylamino-5H-benzo(a)phenoxazine-5-one;nile red

Chemical Property of Nile red

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.5E-09mmHg at 25°C
• Melting Point: 203-205 °C(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 484.7°C at 760 mmHg
• PKA: 4.08±0.20(Predicted)
• Flash Point: 246.9°C
• PSA: 46.34000
• Density: 1.23g/cm³
• LogP: 4.29220
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble1mg/mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 318.136827821
• Heavy Atom Count: 24
• Complexity: 564

Purity/Quality:

98% ^*data from raw suppliers

Nile red ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Azine Dyes
• Canonical SMILES: CCN(CC)C1=CC2=C(C=C1)N=C3C4=CC=CC=C4C(=O)C=C3O2
• 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. A photostable, lipophilic stain with bright red fluorescence Nile Red is a photostable, lipophilic stain with bright red fluorescence. Dyes and metabolites.

Technology Process of Nile red

There total 13 articles about Nile red which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

1,3-dihydroxynaphthalene (132-86-5) + N,N-diethyl-4-nitrosoaniline (120-22-9) → Nile Red (7385-67-3)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 16h;

DOI:10.1021/acs.joc.0c02346

Reference yield: 79.1%

α-naphthol (90-15-3) + 4-nitroso-3-hydroxy-N,N-diethylaniline hydrochloride (25953-06-4) → Nile Red (7385-67-3)

Guidance literature:

In toluene; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201707518

Reference yield: 24.0%

4-nitroso-3-hydroxy-N,N-diethylaniline hydrochloride (25953-06-4) + β-naphthol (135-19-3) → Nile Red (7385-67-3)

Guidance literature:

In N,N-dimethyl-formamide; for 4h; Reflux;

DOI:10.1016/j.tetlet.2008.12.081

upstream raw materials:

2-hydroxynaphtho-1,4-quinone

2-amino-5-(diethylamino)phenol dihydrochloride

α-naphthol

4-nitroso-3-hydroxy-N,N-diethylaniline hydrochloride

Downstream raw materials:

C₂₉H₂₈N₂O₆S

C₂₈H₂₂F₄N₂O

C₂₈H₂₁F₅N₂O

C₂₉H₂₂F₆N₂O

Refernces

• 1、 Klán, Petr,Madea, Dominik,Martínek, Marek,Muchová, Lucie,Váňa, Ji?í,Vítek, Libor. "Structural modifications of nile red carbon monoxide fluorescent probe: Sensing mechanism and applications". . p. 3473 - 3489. Retrieved 2020/03/25.
• 2、 Tang, Juan,Robichaux, Michael A.,Wu, Kuan-Lin,Pei, Jingqi,Nguyen, Nhung T.,Zhou, Yubin,Wensel, Theodore G.,Xiao, Han. "Single-Atom Fluorescence Switch: A General Approach toward Visible-Light-Activated Dyes for Biological Imaging". supporting information. p. 14699 - 14706. Retrieved 2019/10/11.