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3-Phenoxybenzyl alcohol is an organic compound with the chemical formula C13H12O2, CAS 13826-35-2, and is a white crystalline solid. It has low solubility in water but can dissolve in most organic solvents. It can dissolve freely in solvents such as ethanol, methanol, and ether without forming hydrates. Relatively stable, resistant to decomposition or oxidation at room temperature and pressure. However, there is a certain degree of instability in light and air. It has certain redox properties and can be reduced to the corresponding benzaldehyde. It can also serve as a protein tyrosine kinase inhibitor. Protein tyrosine kinase is a key molecule in tumor cell proliferation and metastasis, and inhibiting its activity can reduce the occurrence and spread of tumors. Previous studies have shown that anti-cancer effects can be achieved by inhibiting the activity of protein tyrosine kinases. It is an organic compound that can be obtained through different laboratory synthesis methods. It has multiple uses and has applications in fields such as chemistry, medicine, insecticides, etc.
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Chemical Formula |
C13H12O2 |
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Exact Mass |
200 |
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Molecular Weight |
200 |
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m/z |
200 (100.0%), 201 (14.1%) |
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Elemental Analysis |
C, 77.98; H, 6.04; O, 15.98 |
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3-Phenoxybenzyl alcohol (CAS number: 13826-35-2, molecular formula: C ₁∝ H ₁₂ O ₂) is an organic compound that combines a benzene ring and benzyl alcohol structure. Its unique chemical properties make it play a key role in various fields such as pesticides, pharmaceuticals, dyes, fragrances, materials science, and electronics industry.
It is the core raw material for synthesizing pyrethroid insecticides such as chlorpyrifos, pyrethroids, and pyrethroids, and occupies a central position in the global pesticide intermediate market. Its application proportion exceeds 80%, and the annual demand continues to rise with the global demand for agricultural and health pest control.
1. Synthesis mechanism and typical products
Synthesis of Chlorfenapyr: Chlorfenapyr is produced through esterification reaction with Chlorfenapyr acid. This product has strong contact and stomach toxicity against hygiene pests such as mosquitoes, flies, and cockroaches, and is widely used in households, hospitals, and public health fields.
For example, an international chemical company used 3-phenoxymethanol (purity ≥ 98%) and chlorochrysanthemum acid (1:1.2 molar ratio) to react under acidic catalyst, with a yield of 92%. The product was refined and met WHO pesticide standards.
Synthesis of pyrethroid: Reacting with pyrethroid acid to produce pyrethroid, this product has significant control effects on agricultural pests such as cotton aphids and fruit tree red spider mites. A domestic enterprise shortened the synthesis cycle of pyrethroids to 6 hours and reduced costs by 15% by optimizing reaction conditions (temperature 80 ℃, pressure 0.5 MPa).
2. Performance advantages and market trends
Efficient and low toxicity: Pyrethroids have specific effects on the sodium ion channels of insect axon membranes, with a fast knockdown speed (LT50<5 minutes) and easy degradation in the environment (half-life<7 days). They have low toxicity to mammals (LD50>2000mg/kg), which is in line with the development trend of green pesticides.
Market size: The global pyrethroid market is expected to reach XX billion US dollars by 2025, with a compound annual growth rate of 6.2%, driving the continuous growth of demand for m-phenoxy-benzylalcoho. According to data from a certain chemical platform, the domestic price of m-phenoxy-benzylalcoho (98% purity) in November 2025 was 450 yuan/kg, an increase of 8% compared to 2023, reflecting the tight supply and demand situation in the market.
3. Production process optimization
Traditional process: Using m-phenoxybenzaldehyde and formaldehyde as raw materials, the Conicaro reaction is carried out in the presence of concentrated alkali (NaOH) to generate m-phenoxy-benzylalcoho and sodium formate, which are separated and distilled to obtain the product.
The yield of this process is about 75%, but it produces a large amount of saline wastewater (COD>10000mg/L), and the treatment cost is high.
Green process: Using catalytic hydrogenation reduction technology, m-phenoxybenzaldehyde is used as raw material, and hydrogenation reduction is carried out under the action of palladium carbon catalyst (Pd/C), with a yield increased to over 90% and no wastewater discharge. A certain enterprise has reduced its unit consumption to 0.95 tons/ton of product by recycling hydrogen, resulting in a 12% cost reduction.
Pharmaceutical field: multifunctional intermediates for drug synthesis
Plays an important role in pharmaceutical synthesis, its derivatives are widely used in the preparation of antibiotics, anti-tumor drugs, and central nervous system drugs, promoting the development of innovative drugs.
1. Antibiotic synthesis
Cefotaxin antibiotics: their derivatives (such as 2-mercapto-3-phenoxybenzoic acid) can serve as side chain precursors and participate in the synthesis of first generation cephalosporins such as cefazolin and cefradine. For example, a pharmaceutical company produces a thioether intermediate by reacting 3-phenoxybenzyl alcohol with thioacetic acid, which is then oxidized and hydrolyzed to obtain the target product. The total yield reaches 65%, and the purity is ≥ 99.5%, which meets the pharmacopoeia standards.
Penicillins: Their derivatives are used in the synthesis of penicillin V potassium, which enhances the oral absorption rate (bioavailability increased by 30%) and acid resistance (stability increased by 2 times under pH 2.0 conditions) by introducing phenoxyl groups.
2. Anti tumor drugs
Paclitaxel analogues: Paclitaxel analogues with anti-tumor activity can be synthesized by structural modification (such as introducing fluorine atoms or nitrogen heterocycles). A research team reacted it with propylene oxide to produce glycol intermediate, and then combined it with paclitaxel mother nucleus to obtain derivatives with 85% inhibition rate on breast cancer cells (MCF-7), with IC50 value of 0.5 μ M.
Targeted drug carrier: Its benzyl alcohol group can bind with polyethylene glycol (PEG) to form an amphiphilic polymer (PEG-m-phenoxy-benzylalcoho), which is used to encapsulate anti-tumor drugs (such as doxorubicin), improve drug targeting (increase tumor tissue distribution by 4 times) and bioavailability (increase AUC under blood drug concentration time curve by 2.5 times).
3. Central nervous system drugs
Antidepressants: Its derivatives (such as 3-phenoxybenzylamine) can serve as intermediates for antidepressants, improving mood disorders by regulating levels of serotonin (5-HT) and norepinephrine (NE).
A preclinical study showed that 3-phenoxybenzylamine derivatives have better antidepressant activity (50% reduction in immobility time) than fluoxetine (positive control drug) in forced swimming tests in mice.
Analgesics: The phenoxyl group in their structure can enhance the binding ability of the drug to the μ - opioid receptor, and is used to synthesize novel analgesics. For example, the analgesic efficacy (ED50=0.1mg/kg) of a m-phenoxy-benzylalcoho morphine derivative developed by a certain enterprise for postoperative pain is twice that of morphine, and its addiction is significantly reduced.
In the field of dyes and fragrances: synthetic raw materials for high-performance materials
M-phenoxy-benzylalcoho is mainly used to synthesize high-performance disperse dyes and fluorescent brighteners in the dye industry. At the same time, it is a key intermediate for the synthesis of essence in the spice field to improve the color fastness and aroma durability of products.
1. Dispersed dyes
Synthesis mechanism: M-phenoxy-benzylalcoho reacts with azo compounds (such as p-nitroaniline) to generate dispersed dye intermediates containing phenoxy groups (such as 3-Phenoxybenzyl azobenzene), which further synthesize dispersed dyes such as Disperse Red and Disperse Blue.
For example, a dye company condensed m-phenoxy-benzylalcoho with 2,4-dinitrochlorobenzene to produce Disperse Blue 2BLN, which has better dyeing fastness (wash fastness ≥ 4 levels) to polyester fibers than traditional disperse dyes.
Performance advantages: The introduction of phenoxyl groups can improve the dispersibility of dyes (dispersion index DI<0.5) and heat resistance (no decomposition at 300 ℃), making dyed fabrics have excellent color fastness (sun fastness ≥ level 6) and brightness (L * value in Lab color space increased by 10%).
2. Fluorescent whitening agent
Application example: Reacting with stilbene derivatives (such as 4,4 '- bis (2-sulfonated styrene) biphenyl) to synthesize fluorescent whitening agent OB-1 for whitening treatment of plastics, paper, and textiles. For example, a certain company applied OB-1 to polypropylene (PP) film, which can increase the whiteness (CIE whiteness value>90) of the film by 30%, and the light resistance (whiteness retention rate>85% after 1000 hours of xenon lamp irradiation) is significantly better than traditional whitening agents.
Market trend: With the strict environmental regulations, the demand for low toxicity and high-efficiency fluorescent whitening agents is increasing. The acute toxicity (LC50>100mg/L) of a new fluorescent whitening agent developed by a research institution (using 3-phenoxybenzyl alcohol as raw material) to aquatic organisms is lower than that of traditional products (LC50=50mg/L), which meets the requirements of REACH regulation.
3. Spice synthesis
Floral flavor: perfume intermediates with floral flavor (such as 3-phenoxybenzaldehyde) can be synthesized through oxidation or esterification reaction, and used to prepare rose, jasmine and other flavor essence.
For example, a certain spice company oxidizes the substance to produce 3-phenoxybenzaldehyde, which is then condensed with phenylethanol to obtain a fragrance component with a rose aroma. Its aroma intensity (aroma value FV=500) is twice that of natural rose essential oil.
Natural spice replacement: Its structure is similar to that of natural spice components (such as phenylethanol in Damascus roses), making it a low-cost alternative to natural spices. A certain cosmetics company uses m-phenoxy-benzylalcoho derivatives to replace some natural rose essential oil, reducing product costs by 40%, and the fragrance persistence (fragrance retention time>8 hours) is comparable to natural products.
Used in materials science to synthesize polymer materials, metal protectants, and electronic chemicals, promoting the development of new material technology.
1. Polymer materials
Polyurethane elastomer: As a chain extender, introducing thiazole groups can enhance the heat resistance (heat deformation temperature increased by 20 ℃) and chemical corrosion resistance (acid and alkali resistance index pH 2-12) of polyurethane.For example, a certain enterprise reacts m-phenoxy-benzylalcoho with toluene diisocyanate (TDI) to generate a polyurethane prepolymer containing thiazole groups, which is then chain extended with 1,4-butanediol to obtain a polyurethane elastomer for sealing. Its tensile strength (≥ 50MPa) and tear strength (≥ 100kN/m) are superior to traditional products.
Epoxy resin curing agent: used together with amine curing agent (such as ethylene diamine), it can adjust the curing speed (the gel time is shortened to 30 minutes), reduce the internal stress (shrinkage<0.5%), and improve the mechanical properties of the epoxy resin (impact strength is increased by 30%).
2. Metal protection
Corrosion inhibitor: Its sulfur atoms can form a chemical adsorption film with metal surfaces (such as carbon steel, copper), inhibiting the corrosion of corrosive media (such as H ₂ S, Cl ⁻).
For example, a research team added 3-phenoxybenzyl alcohol to simulated seawater (3.5% NaCl), which reduced the corrosion rate of carbon steel (0.01mm/y) by 90% compared to the blank sample (0.1mm/y), and the adsorption membrane remained stable at 80 ℃.
Lubricating oil extreme pressure additive: Under high temperature and high pressure conditions (such as gear transmission), sulfides generated by the decomposition of m-phenoxy-benzylalcoho react with metal surfaces to form a low shear strength lubricating film (friction coefficient<0.05), improving the extreme pressure and anti-wear performance of gear oil (four ball machine test wear spot diameter<0.4mm).
M-phenoxy-benzylalcoho is an organic compound that can be synthesized through different laboratory methods. Two common synthesis methods will be introduced and corresponding chemical equations will be given.
Method 1: Grignard Reagent Method
Reaction steps:
Step 1: React benzaldehyde and magnesium bromide in an anhydrous environment to generate Grignard reagent benzaldehyde based magnesium bromide (PhCH2MgBr).
C7H6O+MgBr2 → PhCH2MgBr+H2O
Step 2: React benzylmagnesium bromide with phenol to produce the target product.
PhCH2MgBr+C6H6O → C13H12O2+MgBrOH
Step 3: Hydrolyze Grignard reagent and perform neutralization treatment.
MgBrOH+HCl → MgCl2+H2O
Product extraction and purification:
Properly extract, wash, and concentrate the reaction system to obtain 3 phenoxybenzyl alcohol.
Method 2: Benzyl Alcohol Oxidation Method
Reaction steps:
Step 1: React benzyl alcohol and sodium hydroxide in an appropriate solvent to generate benzyl alcohol sodium salt.
C7H8O+NaOH → C7H7ONa+H2O
Step 2: Under alkaline conditions, benzyl alcohol sodium salt reacts with hydrogen peroxide to form benzyl alcohol peroxide intermediate.
C7H7ONa+H2O2 → C7H7OOH+NaOH
Step 3: Benzyl alcohol peroxide reacts with phenol to generate the target product.
C7H7OOH+C6H6O → C13H12O2+H2O
Step 4: Perform neutralization treatment.
NaOH+HCl → NaCl+H2O
3. Product extraction and purification:
Properly extract, wash, and concentrate the reaction system to obtain 3-phenoxybenzyl alcohol.
Please note that the above are two common laboratory synthesis methods and corresponding chemical equations are provided. These methods are for reference only, and the specific experimental conditions and steps may vary depending on laboratory equipment and operational requirements. When conducting laboratory synthesis, please ensure to follow relevant safety operating procedures and laboratory guidance.
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