2-Naphthalenol, 1-[2-[4-(2-phenyldiazenyl)phenyl]diazenyl]- (CAS 85-86-9) — Citrus N/A Note Fragrance Ingredient
2-Naphthalenol, 1-[2-[4-(2-phenyldiazenyl)phenyl]diazenyl]-
CAS 85-86-9
What Is 2-Naphthalenol, 1-[2-[4-(2-phenyldiazenyl)phenyl]diazenyl]-?
This synthetic compound is a specialized dye and fragrance ingredient primarily used in industrial applications. Consumers might encounter trace amounts in certain colored cosmetics or textiles. While not commonly found in consumer products, it serves as a colorant with potential secondary olfactory effects in niche formulations.
Safety Profile
PROFESSIONAL USEWhat Does 2-Naphthalenol, 1-[2-[4-(2-phenyldiazenyl)phenyl]diazenyl]- Smell Like?
No characteristic odor data available for this compound. As a diazo compound, it may exhibit faint aromatic chemical notes if volatile, but primarily functions as a colorant rather than a fragrance ingredient. Molecular structure suggests potential for subtle phenolic or naphthalenic nuances.
2D Molecular Structure
SMILES: OC1=C(N=NC2=CC=C(C=C2)N=NC2=CC=CC=C2)C2=CC=CC=C2C=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
This compound belongs to the diazo dye chemical class, featuring two azo groups (-N=N-) bridging aromatic systems. Synthesized through diazotization and coupling reactions, these compounds are valued for their intense coloration properties. The naphthalene core contributes to molecular stability while the phenyl groups influence solubility characteristics. No chiral centers are present in this planar, conjugated system.
Physical & Chemical Properties
| Molecular Type | Synthetic diazo compound |
|---|---|
| Primary Use | Industrial dye |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Industrial | Trace | 0.01-0.1% | Colorant applications only |
Classic Accords
Tip: Not recommended for perfumery applications due to limited olfactory characteristics and safety profile.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not evaluated by IFRA – industrial use only.
RIFM Assessment
No RIFM evaluation available for this compound.
Sustainability
As a synthetic dye compound, production involves petrochemical feedstocks and energy-intensive processes. No known natural alternatives exist for this specific structure. Environmental impact primarily relates to potential persistence in wastewater systems due to aromatic stability.
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Ingredient Data Sheet
CAS 85-86-9Physical Properties
| Molecular Weight | 352.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 5.9🔬 PubChem |
| Boiling Point | 361 °C🔬 EPA CompTox |
| Vapor Pressure | 0 mmHg @ 25°C📊 OPERA |
| Flash Point | 398.1 °C🔬 EPA CompTox |
| log Kp (skin permeability) | -0.661💻 Calculated |
| SMILES | C1=CC=C(C=C1)N=NC2=CC=C(C=C2)N=NC3=C(C=CC4=CC=CC=C43)O🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
Odor & Flavor
| Functional Groups | phenolaromatic💻 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: DTXSID3041742
Physical Properties
| Molecular Weight | 352.397 g/mol🔬 EPA CompTox |
| Density | 1.205 g/cm^3📊 OPERA |
| Boiling Point | 472.798 °C📊 OPERA |
| Melting Point | 195 °C🔬 EPA CTX |
| Flash Point | 369.998 °C📊 OPERA |
| Refractive Index | 1.662 Dimensionless📊 OPERA |
| Molar Volume | 288.681 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.2 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 5.2 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.195 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 10.6 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0 mmHg📊 OPERA |
| Surface Tension | 50.434 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 69.67 Ų💻 Computed |
| H-Bond Donors | 1 count💻 Computed |
| H-Bond Acceptors | 5 count💻 Computed |
| Rotatable Bonds | 4 count💻 Computed |
| Aromatic Rings | 4 count💻 Computed |
| Molar Refractivity | 106.81 cm^3/mol📊 OPERA |
| Polarizability | 42.343 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.
