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Chemical Identity and Structure
Nomenclature
IUPAC Name: Phenylmethanol
Common Names/Synonyms: Benzyl alcohol, Benzenemethanol, Hydroxybenzene, α-Hydroxytoluene, Phenylcarbinol, α-Cresol, α-Toluenol, Benzyl hydroxide
CAS Number: 100-51-6
EINECS Number: 202-859-9
PubChem CID: 244
SMILES: c1ccc(cc1)CO
InChI Key: WVDDGKGOMKODPV-UHFFFAOYAH
Molecular Structure
Molecular Formula: C₆H₅CH₂OH
Molecular Weight: 108.14 g/mol
Structural Features: Benzyl alcohol consists of a phenyl ring attached to a primary alcohol group (-CH₂OH).
The hydroxyl group imparts polarity, solubility in water, and reactivity toward oxidizing agents.
The benzene ring provides aromatic stability and hydrophobic characteristics, balancing its solubility profile.
Physical Properties
Appearance: Colorless, viscous liquid
Odor: Mild aromatic
Density: 1.044 g/cm³
Melting Point: −15.2°C
Boiling Point: 205.3°C
Refractive Index: 1.541 at 20°C
Vapor Pressure: 0.18 kPa at 60°C
Solubility: Miscible with water, ethanol, ether, chloroform
Chemical Properties
Functional group: Primary alcohol
Reactivity: Can undergo oxidation, esterification, etherification, and substitution reactions.
Stability: Stable under normal temperature and pressure but can oxidize slowly in air to benzaldehyde and then benzoic acid.
Synthesis of Benzyl Alcohol
Benzyl alcohol can be produced industrially or in laboratory settings through multiple pathways:
From Toluene
Catalytic hydroxymethylation: Toluene reacts with formaldehyde in the presence of basic catalysts or hydrogen peroxide to form benzyl alcohol.
Advantages: Uses readily available toluene as feedstock.
Disadvantages: Requires careful control to prevent over-oxidation to benzoic acid.
From Benzaldehyde
Cannizzaro Reaction: Benzaldehyde is treated with concentrated sodium hydroxide, producing benzyl alcohol and sodium benzoate via disproportionation.
Stoichiometry: 2 C₆H₅CHO + NaOH → C₆H₅CH₂OH + C₆H₅COONa
Industrial relevance: Less common than toluene oxidation due to cost.
From Benzyl Chloride
Reduction with NaBH₄ or LiAlH₄: Benzyl chloride is reduced to benzyl alcohol using mild hydride donors.
Advantages: High yields, suitable for laboratory synthesis.
Disadvantages: Hazardous reagents; not always scalable industrially.
Biotechnological Methods
Microbial transformation of toluene derivatives using specific strains of Pseudomonas can generate benzyl alcohol under mild conditions.
Green chemistry advantage: Reduces hazardous waste.
Chemical Reactions of Benzyl Alcohol
Oxidation
Partial oxidation: Benzyl alcohol → benzaldehyde
Complete oxidation: Benzyl alcohol → benzoic acid
Catalysts: Copper, manganese dioxide, or oxygen with metal catalysts.
Esterification
Reacts with carboxylic acids or acyl chlorides to form benzyl esters (e.g., benzyl acetate).
Applications: Perfumes, flavors, and plasticizers.
Ether Formation
Condensation of two benzyl alcohol molecules under acidic conditions forms dibenzyl ether.
Applications: Organic synthesis intermediates, lubricants, and solvents.
Substitution Reactions
Can undergo halogenation at the benzylic position to produce benzyl halides.
Benzylic position is highly reactive due to resonance stabilization of the radical or carbocation.
Other Reactions
Reaction with acids, bases, and oxidizing agents allows benzyl alcohol to act as a versatile intermediate in chemical synthesis.
Industrial Applications
Solvent Applications
Widely used as a solvent for paints, coatings, inks, epoxy resins, and adhesives due to its polarity and low toxicity.
Solubilizes hydrophobic compounds while being miscible with water and alcohols.
Chemical Intermediate
Precursor for esters and ethers (e.g., benzyl benzoate, benzyl salicylate, dibenzyl ether)
Used in the manufacture of pharmaceuticals, flavors, fragrances, and plasticizers.
Dye and Pigment Industry
Solvent for wool, nylon, and leather dyeing processes.
Enhances dispersion of pigments.
Pharmaceutical Uses
Local anesthetic: Topical formulations for pain relief.
Bacteriostatic preservative: Used in injectables, ophthalmic, and topical medications.
Head lice treatment: 5% benzyl alcohol lotion approved by FDA.
Cosmetic and Personal Care
Preservative in skincare and haircare products.
Solvent for essential oils, fragrances, and active ingredients.
Provides mild scent and stability to formulations.
Food Industry
Food additive: E1519, authorized for flavoring or preservative purposes in certain EU foods.
Flavoring agent: Contributes mild aromatic notes.
SAFETY INFORMATION ABOUT BENZOL ALCOHOL
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
