3-Methylbenzyl alcohol
[CAS# 587-03-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: 3-Methylbenzyl alcohol
• Synonyms: (3-methylphenyl)methanol
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.16
• CAS Registry Number: 587-03-1
• EC Number: 209-595-3
• SMILES: CC1=CC(=CC=C1)CO

Properties

• Density: 1.013 g/mL (Expl.)
• Melting point: -20 ºC (Expl.)
• Boiling point: 215 ºC (740 mmHg) (Expl.)
• Refractive index: 1.534 (Expl.)
• Flash point: 105 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

3-Methylbenzyl alcohol, also known as m-tolylmethanol, is an aromatic alcohol that features a methyl group (-CH3) attached to the benzene ring at the meta position relative to the hydroxymethyl group (-CH2OH). Its chemical formula is C8H10O, and it is a colorless, sweet-smelling liquid with a mild floral odor, commonly used in the fragrance and flavor industries. The compound’s discovery can be attributed to ongoing research in the field of aromatic chemistry, which focuses on modifying the properties of aromatic compounds to enhance their reactivity and utility in various industrial applications.

The synthesis of 3-methylbenzyl alcohol typically involves the reduction of 3-methylbenzaldehyde, which is prepared by the methylation of benzaldehyde in the presence of a methylating agent such as methyl iodide or dimethyl sulfate. The reduction process is commonly carried out using reducing agents like sodium borohydride (NaBH4) or catalytic hydrogenation. This reaction selectively reduces the aldehyde group (-CHO) to a primary alcohol group (-CH2OH), resulting in the formation of 3-methylbenzyl alcohol. This process is highly efficient and widely used in both laboratory and industrial settings for the production of the compound.

3-Methylbenzyl alcohol has a variety of applications in different industries due to its pleasant scent and versatile chemical properties. One of its most significant uses is in the fragrance industry, where it is used as a component in perfumes and cosmetics. The compound’s sweet, floral odor makes it an excellent choice for creating floral, woody, or fruity fragrance notes. It is often included in the formulation of perfumes, colognes, soaps, and lotions, adding depth and complexity to scent profiles. Additionally, it is used in the food and beverage industry as a flavoring agent to impart a fruity or floral taste to a variety of products, including beverages, candies, and baked goods.

Another important application of 3-methylbenzyl alcohol is in the production of resins and polymers. Due to its hydroxymethyl group, the compound can act as a building block for the synthesis of various resins, particularly phenolic resins, which are widely used in the automotive, electronics, and construction industries. These resins are valued for their high thermal stability and excellent adhesive properties. The hydroxymethyl group in 3-methylbenzyl alcohol allows it to easily react with other chemical components, making it a useful intermediate in the synthesis of cross-linked polymer networks.

The compound is also employed in the synthesis of pharmaceuticals and agrochemicals. It can serve as an intermediate in the production of active pharmaceutical ingredients (APIs) that require the introduction of an aromatic alcohol group. Additionally, 3-methylbenzyl alcohol is used in the synthesis of certain pesticides and herbicides. Its ability to modify the structure of organic compounds makes it a useful reagent for the creation of novel chemical agents with specific biological activities. The compound’s relatively low toxicity and ease of synthesis further enhance its appeal for such applications.

Moreover, 3-methylbenzyl alcohol has been explored for its potential use in various chemical reactions as a solvent or intermediate. It can be involved in nucleophilic substitution reactions, where the hydroxymethyl group can act as a nucleophile, and its methyl group can participate in electrophilic aromatic substitution reactions. This reactivity allows it to be used in the development of new materials, including fine chemicals, and in synthetic organic chemistry.

In conclusion, 3-methylbenzyl alcohol is a versatile compound with a wide range of applications in the fragrance, polymer, pharmaceutical, and agrochemical industries. Its ability to enhance the properties of various chemical products, combined with its mild, pleasant scent, makes it an essential ingredient in many formulations. Ongoing research into its applications and reactivity continues to expand its potential uses, particularly in the synthesis of high-performance materials and bioactive molecules.