9,10-Anthracenedione, 1,4-bis[(2,4,6-trimethylphenyl)amino]- (CAS 116-75-6) — Citrus N/A Note Fragrance Ingredient
9,10-Anthracenedione, 1,4-bis[(2,4,6-trimethylphenyl)amino]-
CAS 116-75-6
What Is 9,10-Anthracenedione, 1,4-bis[(2,4,6-trimethylphenyl)amino]-?
9,10-Anthracenedione, 1,4-bis[(2,4,6-trimethylphenyl)amino]- is a synthetic dye and specialty chemical used in industrial applications. Consumers may encounter it in very trace amounts as a colorant in certain plastics or coatings. This compound is not commonly used in consumer fragrance products due to its limited olfactory properties and specialized applications.
Safety Profile
PROFESSIONAL USEWhat Does 9,10-Anthracenedione, 1,4-bis[(2,4,6-trimethylphenyl)amino]- Smell Like?
This anthracenedione derivative is primarily valued for its dye properties rather than fragrance characteristics. As a functional chemical, it lacks distinctive olfactory notes that would be relevant in perfumery. The molecular structure suggests minimal volatility and no significant aroma profile suitable for fragrance applications.
2D Molecular Structure
SMILES: CC1=CC(C)=C(NC2=CC=C(NC3=C(C)C=C(C)C=C3C)C3=C2C(=O)C2=CC=CC=C2C3=O)C(C)=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
This compound belongs to the anthraquinone dye class, featuring a central anthracenedione core with dimethylaniline substituents. The conjugated system provides color properties but limited fragrance potential. Industrial synthesis typically involves condensation reactions of anthraquinone derivatives with substituted anilines under controlled conditions.
Physical & Chemical Properties
| Appearance | Solid crystalline material |
|---|---|
| Primary Use | Industrial dye applications |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Industrial | N/A | N/A | Specialty chemical applications only |
Classic Accords
Tip: Not recommended for fragrance use.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not evaluated by IFRA – industrial chemical outside scope.
GHS Classification
RIFM Assessment
Not assessed by RIFM – industrial application only.
Sustainability
Production involves petrochemical feedstocks and specialized synthesis routes. Environmental impact primarily relates to industrial waste management rather than consumer product considerations.
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Ingredient Data Sheet
CAS 116-75-6Physical Properties
| Molecular Weight | 474.6 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 9.2🔬 PubChem |
| Boiling Point | 462 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 465 °C🔬 EPA CompTox |
| log Kp (skin permeability) | 0.937💻 Calculated |
| SMILES | CC1=CC(=C(C(=C1)C)NC2=C3C(=C(C=C2)NC4=C(C=C(C=C4C)C)C)C(=O)C5=CC=CC=C5C3=O)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Functional Groups | ketonearomaticamine💻 RDKit |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID3051593
Physical Properties
| Molecular Weight | 474.604 g/mol🔬 EPA CompTox |
| Density | 0.836 g/cm^3🔬 EPA CTX |
| Boiling Point | 551.616 °C📊 OPERA |
| Melting Point | 242 °C🔬 EPA CTX |
| Flash Point | 465 °C🔬 EPA CTX |
| Refractive Index | 1.677 Dimensionless📊 OPERA |
| Molar Volume | 388.798 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 6.789 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 6.789 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 6.789 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 9.74 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 56.321 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 58.2 Ų💻 Computed |
| H-Bond Donors | 2 count💻 Computed |
| H-Bond Acceptors | 4 count💻 Computed |
| Rotatable Bonds | 4 count💻 Computed |
| Aromatic Rings | 4 count💻 Computed |
| Molar Refractivity | 146.367 cm^3/mol📊 OPERA |
| Polarizability | 58.024 Å^3📊 OPERA |
Data Sources:
🔬 EPA Experimental data from U.S. EPA CompTox Chemicals Dashboard & CTX APIs. 📊 OPERA Predicted using EPA's OPERA QSAR models. 💻 Computed Calculated from SMILES using RDKit.
