(4-tert-Butylphenyl)acetonitrile (CAS 3288-99-1) — Green Middle Note Fragrance Ingredient
(4-tert-Butylphenyl)acetonitrile
CAS 3288-99-1
What Is (4-tert-Butylphenyl)acetonitrile?
(4-tert-Butylphenyl)acetonitrile is a synthetic fragrance ingredient primarily used in perfumery. It’s found in niche perfumes and some personal care products, contributing to modern accords. This molecule matters because it adds a unique aromatic dimension to fragrances, helping create distinctive scent profiles that stand out in competitive markets while being cost-effective compared to some natural alternatives.
Safety Profile
USE WITH AWARENESSWhat Does (4-tert-Butylphenyl)acetonitrile Smell Like?
This synthetic nitrile delivers a sharp, clean aromatic character with subtle floral undertones. Initially presents a crisp, almost metallic greenness that evolves into a warmer, ambery dry-down. The tert-butyl group lends a distinctive woody-herbal quality, while the nitrile function provides piercing intensity. Acts like an aromatic chameleon – in low doses it brightens citrus accords, while higher concentrations contribute to masculine leather and fougère compositions. The dry-down reveals a persistent, slightly powdery residue reminiscent of almond skins.
In Famous Fragrances
Fragrance associations may not reflect actual formulations.
Used as a modern green-aromatic modifier to enhance the synthetic freshness of this aquatic classic, contributing to its sharp opening and helping bridge marine notes to woody base.
Provides a crisp, clean facet that complements the watery lotus accord, adding structural definition to this transparent floral-aquatic composition.
2D Molecular Structure
SMILES: CC(C)(C)C1=CC=C(CC#N)C=C1
Chemistry, Properties & Perfumer Guide
The Chemistry
(4-tert-Butylphenyl)acetonitrile belongs to the arylacetonitrile class, characterized by a benzene ring substituted with both a tert-butyl group and an acetonitrile moiety. The tert-butyl group provides steric bulk that influences volatility and odor characteristics. Synthesized via Friedel-Crafts alkylation of benzene derivatives followed by cyanoethylation. The planar aromatic system conjugated with the nitrile group creates a rigid molecular structure that contributes to its tenacious odor profile. No chiral centers present.
Physical & Chemical Properties
| Molecular Weight | 175.24 g/mol |
|---|---|
| XLogP | 3.1 (estimated) |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Used as aromatic enhancer |
| Functional Fragrance | 0.1-0.5% | Up to 1% | For soap and detergent applications |
Classic Accords
Tip: Use with citrus top notes to prevent harshness – the nitrile group can amplify bitterness if overdosed.
Alternatives & Comparisons
More floral and less woody, suitable when a softer nitrile character is desired without the tert-butyl influence.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA standards.
RIFM Assessment
Not currently evaluated by RIFM – recommended for limited use pending further studies.
Sustainability
As a synthetic material, production doesn’t rely on agricultural resources. Manufacturing typically involves petrochemical feedstocks, though modern routes may incorporate greener chemistry principles. The nitrile group requires careful handling to prevent environmental release during production.
Explore (4-tert-Butylphenyl)acetonitrile
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References
- Bauer et al. (2001). Common Fragrance and Flavor Materials. Wiley-VCH.
Data: PubChem (NIH), PubMed, RIFM, IFRA. Last reviewed: Apr 2026.
Report a data errorPhysicochemical Properties
DTXSID: DTXSID8052011
Physical Properties
| Molecular Weight | 173.259 g/mol🔬 EPA CompTox |
| Density | 0.958 g/cm^3📊 OPERA |
| Boiling Point | 277.637 °C📊 OPERA |
| Melting Point | 23.482 °C📊 OPERA |
| Flash Point | 125.845 °C📊 OPERA |
| Refractive Index | 1.505 Dimensionless📊 OPERA |
| Molar Volume | 182.321 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 3.315 Log10 unitless📊 OPERA |
| LogD (pH 5.5) | 3.315 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 3.315 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 5.81 Log10 unitless📊 OPERA |
| Water Solubility | 0.001 mol/L📊 OPERA |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.028 mmHg📊 OPERA |
| Viscosity | 2.99 cP📊 OPERA |
| Surface Tension | 33.932 dyn/cm📊 OPERA |
| Thermal Conductivity | 139.405 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 | 1 count💻 Computed |
| Aromatic Rings | 1 count💻 Computed |
| Molar Refractivity | 54.103 cm^3/mol📊 OPERA |
| Polarizability | 21.448 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.
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