2-Benzyl-2-methylbut-3-enenitrile (CAS 97384-48-0) — Green Top to Middle Note Fragrance Ingredient
2-Benzyl-2-methylbut-3-enenitrile
CAS 97384-48-0
What Is 2-Benzyl-2-methylbut-3-enenitrile?
2-Benzyl-2-methylbut-3-enenitrile is a synthetic fragrance ingredient used in modern perfumery. It’s found in fine fragrances and personal care products, often as part of fresh, green, or floral accords. This nitrile compound is valued for its ability to add crisp, clean facets to compositions, frequently appearing in unisex and masculine fragrances where a modern twist on classic fougère structures is desired.
Safety Profile
USE WITH AWARENESSWhat Does 2-Benzyl-2-methylbut-3-enenitrile Smell Like?
2-Benzyl-2-methylbut-3-enenitrile delivers a sharp, green opening with distinct metallic undertones, like freshly crushed stems. The initial burst evolves into a cleaner, more diffusive heart recalling rainwater on hot pavement. As it dries down, subtle woody-ambery facets emerge, anchored by a persistent nitrile character that provides excellent tenacity. The overall effect is modern and abstract – imagine the crispness of a just-opened tech gadget combined with the coolness of alpine air.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used to amplify the modern freshness of the citrus-woody structure, adding a contemporary metallic edge to the classic fougère DNA.
Contributes to the ‘mineral’ accord, enhancing the ambroxan with crisp, clean facets that suggest running water over stones.
Provides the grapefruit accord with extra dimension, creating the illusion of fruit zest without sweetness.
2D Molecular Structure
SMILES: CC(CC1=CC=CC=C1)(C=C)C#N
Chemistry, Properties & Perfumer Guide
The Chemistry
As a branched-chain aliphatic nitrile, 2-benzyl-2-methylbut-3-enenitrile belongs to a class of synthetic aroma chemicals prized for their stability and tenacity. The molecule combines an unsaturated hydrocarbon chain with a benzylic substitution pattern, creating unique electronic effects that influence its odor profile. Industrial synthesis typically proceeds through Grignard reactions or nucleophilic substitutions on pre-formed nitrile precursors. The presence of both sp2 and sp3 hybridized carbons contributes to its complex odor evolution.
Physical & Chemical Properties
| Boiling Point | Not publicly documented |
|---|---|
| Density | Not publicly documented |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used for fresh top notes and modern accords |
| Functional Fragrances | 0.1-0.5% | Up to 1% | Adds clean character to detergents |
Classic Accords
Tip: Use with citrus materials to create ‘metallic fruit’ effects without sweetness.
Alternatives & Comparisons
Offers similar green-metallic characteristics but with more pronounced woody undertones and better diffusion.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted under IFRA standards. General nitrile precautions apply.
GHS Classification
RIFM Assessment
Under evaluation by RIFM as part of nitrile class review.
Sustainability
As a synthetic material, 2-benzyl-2-methylbut-3-enenitrile has negligible agricultural impact. Production typically uses petrochemical feedstocks, though newer green chemistry routes are being explored. The material’s potency means small quantities deliver effect, reducing overall environmental load compared to less powerful ingredients.
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Ingredient Data Sheet
CAS 97384-48-0Physical Properties
| Molecular Weight | 171.24 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 3.1🔬 PubChem |
| Boiling Point | 280 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0229 mmHg @ 25°C📊 OPERA |
| Flash Point | 122 °C🔬 EPA CompTox |
| Involatility Index | 0.0019💻 Calculated |
| log Kp (skin permeability) | -1.544💻 Calculated |
| SMILES | CC(CC1=CC=CC=C1)(C=C)C#N🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 3 / 5💻 Calculated |
Odor & Flavor
| Primary Descriptors | floralgreen• leffingwell |
| Functional Groups | alkenearomatic💻 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: DTXSID7052650
Physical Properties
| Molecular Weight | 171.243 g/mol🔬 EPA CompTox |
| Density | 0.966 g/cm^3🔬 EPA CTX |
| Boiling Point | 277.06 °C📊 OPERA |
| Melting Point | -21.3 °C🔬 EPA CTX |
| Flash Point | 122.5 °C🔬 EPA CTX |
| Refractive Index | 1.522 Dimensionless📊 OPERA |
| Molar Volume | 176.803 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.007 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.007 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.007 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.76 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.013 mmHg📊 OPERA |
| Viscosity | 3.571 cP📊 OPERA |
| Surface Tension | 37.587 dyn/cm📊 OPERA |
| Thermal Conductivity | 147.6 mW/(m*K)📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 23.79 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 1 count💻 Computed |
| Rotatable Bonds | 3 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 53.938 cm^3/mol📊 OPERA |
| Polarizability | 21.383 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.
