Basic information
- CAS
7385-67-3- Standard SMILES
CCN(CC)c1ccc2nc3c4ccccc4c(=O)cc-3oc2c1- InChIKey
VOFUROIFQGPCGE-UHFFFAOYSA-N- Molecular formula
- C20H18N2O2
- Average molar mass
- 318.4 g/mol
- Monoisotopic mass
- 318.13682782
Overview
Nile red is an organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group. It has a role as a fluorochrome and a histological dye. It is an aromatic amine, an organic heterotetracyclic compound, a cyclic ketone and a tertiary amino compound.
Names & identifiers
- Preferred name
- Nile Red
- IUPAC
- 9-(diethylamino)benzo[a]phenoxazin-5-one
- English name
- Nile Red
- Molecular formula
- C20H18N2O2
- Molecular weight
- 318.37
Names & synonyms
Nile red7385-67-39-(diethylamino)-5H-benzo[a]phenoxazin-5-oneNile Blue A OxazoneP476F1L81G9-(Diethylamino)-5H-benzo(a)phenoxazin-5-oneDTXSID7064653CHEBI:521695H-Benzo[a]phenoxazin-5-one, 9-(diethylamino)-5H-Benzo(a)phenoxazin-5-one, 9-(diethylamino)-RefChem:165925DTXCID4047593
Show more names
Fluorescent Spectral Standard E, certifiednilenilereddyePhenoxazoneOxazine O-17MNile Red ,99%Phenoxazone 9
9-diethylamino-5h-benzo(a)phenoxazine-5-one230-966-09-(diethylamino)benzo[a]phenoxazin-5-oneMFCD00011639Nile Blue A oxazone;Phenoxazone 98-(diethylamino)-12H-10-oxa-5-azatetraphen-12-oneMLS0011641979-(diethylamino)benzo[a]phenoxazin-5(5H)-one
Database identifiers
- CAS
7385-67-3- PubChem CID
- 65182
- DTXSID
DTXSID7064653- ChEMBL
CHEMBL144472- ChEBI
CHEBI:52169- UNII
- P476F1L81G
- EC Number
- 230-966-0
- Nikkaji
- J278.800D
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 41.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 564
Experimental & physicochemical properties
Chemical ClassesDyes -> Azine Dyes
Physical DescriptionBrown glistening solid with a faint metallic green reflex; [Merck Index] Dark green crystalline solid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 203 · 203-205 °C(lit.)
- Boiling point
- 457.53 °C · 457.53°C (rough estimate)
- Density
- 1.1871 · 1.1871 (rough estimate)
- refractive index
- 1.57 · 1.5700 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mg/mL · methanol: soluble1mg/mL
- form
- Powder
- pka
- 4.08 · 4.08±0.20(Predicted)
- color
- Dark red to maroon
- Appearance
- Green to Dark Green Solid
- λmax
- 553 nm · 553 nm
- BRN
- 279110 · 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 · 7385-67-3(CAS DataBase Reference)
- FDA UNII
- 476 F1L81G · P476F1L81G
- EPA Substance Registry System
- 5 H-Benzo[a]phenoxazin-5-one, · 5H-Benzo[a]phenoxazin-5-one, 9-(diethylamino)- (7385-67-3)
- UNSPSC Code
- 12171500 · 12171500
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- F
- 8 · 8-10
- TSCA
- TSCA listed
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Hazard information
Hazards SummaryNot considered hazardous by GHS classification; [Sigma-Aldrich MSDS] See Nile Blue
Safety data
- F
- 8-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29349990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Uses & manufacturing
UsesUsed as a polarity-sensitive fluorescent probe of lipids and proteins; [Merck Index]
General Manufacturing Information5H-Benzo[a]phenoxazin-5-one, 9-(diethylamino)-: ACTIVE
Applications
DescriptionNile Red is an aphotostable and lipophilic stain for intracellular lipids and hydrophobic domains of proteins and also for staining of lysosomal phospholipid inclusions.
UsesNile 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.
General DescriptionNile 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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
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Additional notes
DefinitionNile Red is an organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.
Related reactions
5 records
Compound notes
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