Trimethyl Orthobenzoate (Benzene trimethoxymethyl): Properties, Applications, and Industrial Insights
1. Introduction
Trimethyl Orthobenzoate, also known as Benzene trimethoxymethyl or Benzoic acid trimethyl orthoester, is a key intermediate in organic synthesis. It’s valued across pharmaceutical, flavor, fragrance, and polymer industries for its reactivity as an orthoester and its stability under controlled conditions.
This compound is especially important in esterification, acetalization, and protection reactions — making it a common reagent in fine chemical production, API intermediates, and research chemistry.
2. Informational Section: Chemical Identity and Properties
| Parameter | Details |
|---|---|
| Chemical Name | Trimethyl Orthobenzoate |
| Synonyms | Benzene trimethoxymethyl; Benzoic acid trimethyl orthoester |
| Molecular Formula | C10H14O3 |
| Molecular Weight | 182.22 g/mol |
| CAS Number | 479-13-0 |
| EINECS No. | 207-489-4 |
| Appearance | Colorless to pale yellow liquid |
| Odor | Mild aromatic |
| Boiling Point | ~90–95°C (at reduced pressure) |
| Density | 1.09 g/cm³ (20°C) |
| Solubility | Soluble in organic solvents (ethanol, ether, benzene); hydrolyzes in water |
| Storage Conditions | Store in a cool, dry, well-ventilated area away from moisture |
| Stability | Stable under inert atmosphere; hydrolyzes to methyl benzoate and methanol in water |
3. Navigational Section: Chemical Structure and Reactivity
Trimethyl Orthobenzoate belongs to the orthoester family, characterized by the formula RC(OR′)₃.
It acts as an efficient methylating and acetalizing agent, offering controlled reactivity for formyl and hydroxyl group protection during organic synthesis.
Structural Highlights:
- Central carbon bonded to three methoxy groups.
- Provides a stable acetal intermediate in the presence of acids.
- Reacts with alcohols and acids to form esters and ethers.
These properties make it essential for multi-step syntheses where protection of functional groups and mild reaction conditions are crucial.
4. Informational: Applications and Industrial Use Cases
a. Pharmaceutical Industry
Used as a synthetic intermediate for:
- Esterification reactions in drug intermediates.
- Protection of aldehyde and ketone groups in multistep API production.
- Synthesis of benzyl derivatives and aromatic compounds.
b. Fragrance and Flavor Chemistry
- Serves as a building block for aroma compounds such as benzyl esters.
- Used to produce fragrance intermediates with mild, pleasant aromatic notes.
c. Polymer and Resin Manufacturing
- Functions as a cross-linking agent or chemical modifier to improve material properties.
- Useful in sol-gel synthesis and resin functionalization.
d. Academic and Research Chemistry
- Frequently used in mechanistic organic chemistry studies and reaction optimization.
- Common in protective group chemistry experiments.
5. Commercial Section: Market Overview and Industrial Demand
Trimethyl Orthobenzoate has seen growing interest due to:
- Expanding pharmaceutical intermediate markets.
- Increased demand for specialty aroma chemicals.
- Eco-friendly synthesis trends, where it serves as a mild and controllable reagent.
Regional Demand Highlights:
- Asia-Pacific: Dominates production and export.
- Europe: Focuses on REACH-compliant, high-purity grades.
- North America: Used in R&D, analytical, and specialty manufacturing sectors.
Suppliers typically offer industrial (95–98%), analytical (99%), and pharmaceutical-grade (≥99.5%) purity levels.
6. Transactional Section: Safe Handling, Storage, and Procurement
Handling Guidelines:
- Avoid moisture contact — hydrolysis releases methanol.
- Use gloves and protective eyewear.
- Operate under a fume hood in research environments.
Storage Recommendations:
- Keep tightly sealed in a dry, inert atmosphere (nitrogen or argon).
- Store between 5–25°C, away from oxidizing agents and acids.
Packaging Options:
- Glass bottles (100 mL–1 L) for lab use.
- Steel or HDPE drums (25–200 kg) for industrial applications.
Procurement Compliance:
Trimethyl Orthobenzoate is not a controlled substance and can be legally sourced from certified chemical suppliers.
Ensure compliance with GHS labeling, REACH, and local transport regulations (UN-hazard classification if applicable).
7. Regulatory and Environmental Aspects
| Regulatory Body | Status / Guideline |
|---|---|
| REACH (EU) | Registered substance |
| TSCA (US) | Listed |
| GHS Classification | Irritant (eye, skin) |
| Waste Disposal | Follow local hazardous waste protocols |
| Environmental Impact | Low persistence; hydrolyzes in aqueous systems |
Trimethyl Orthobenzoate poses low chronic toxicity, but due to its methanol release upon hydrolysis, safety protocols are advised during use and disposal.
8. Navigational: Analytical and Quality Testing Methods
Researchers and QC teams verify purity through:
- GC-MS for compositional and trace analysis.
- NMR (¹H, ¹³C) for structure confirmation.
- FT-IR spectroscopy for functional group verification.
- Karl Fischer titration for moisture content.
These analyses ensure the reagent’s suitability for pharmaceutical synthesis or industrial application.
9. Commercial and Research Opportunities
- Bulk sourcing through international chemical manufacturers.
- OEM and toll manufacturing for customized purity grades.
- Collaborations between academic and industrial R&D units for new synthesis routes using Trimethyl Orthobenzoate.
Key Advantage: High reactivity with controllable hydrolysis makes it ideal for sustainable chemistry and green process optimization.
10. Conclusion: Trimethyl Orthobenzoate ONLINE
Trimethyl Orthobenzoate (Benzene trimethoxymethyl) continues to play a critical role as a functional intermediate in organic synthesis, flavor and fragrance formulation, and pharmaceutical manufacturing.
Its combination of reactivity, selectivity, and relative stability under anhydrous conditions has made it an invaluable reagent in modern chemical industries.
When handled responsibly and sourced from compliant suppliers, it offers researchers and manufacturers a versatile, high-purity reagent for diverse industrial and scientific needs.
🔍 Trimethyl Orthobenzoate Keywords:
Trimethyl Orthobenzoate • Benzene trimethoxymethyl • Orthoester reagent • Benzoic acid trimethyl orthoester • Organic synthesis intermediate • Pharmaceutical raw material • Fragrance chemical intermediate • Specialty chemical supplier • REACH-compliant chemical
Applications:
Trimethyl Orthobenzoate is utilized in the synthesis of various chemical compounds. It is employed in the preparation of:
- 5-phenyl-4,6-dipyrrin
- 2,3-orthoester derivatives of ethyl-1-thio-α-L-rhamnopyranoside
- Indol-3-yl-phenyl-methanone through reaction with indole
Solubility:
- Soluble in organic solvents.
Storage and Handling:
- Moisture Sensitivity: Protect from humidity and water.
- Storage Conditions: Keep under dry, inert gas. Store in a cold, dry place.
- Incompatibilities: Avoid contact with oxidizing agents and moisture.
Packaging and Specifications:
- Packaging: Available in 25 kg drums or bags.
- Shelf Life: 2 years
- Grade: Medicine Grade
Purchase Information:
- HS Code: 2933199090
- Production Capacity: 5000 units
To purchase Trimethyl Orthobenzoate, please contact your preferred supplier or visit their website for further details and pricing. Ensure that you comply with all relevant regulations and handling requirements for safe use.
