Trimethoxymethane
[CAS# 149-73-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Trimethoxymethane
• Synonyms: Trimethyl orthoformate; Methyl orthoformate
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.12
• CAS Registry Number: 149-73-5
• EC Number: 205-745-7
• SMILES: COC(OC)OC

Properties

• Density: 0.97
• Melting point: -53 ºC
• Boiling point: 101-102 ºC
• Refractive index: 1.378-1.38
• Flash point: 13 ºC
• Water solubility: 10 g/L (hydrolysis)

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Hazard Statements: H225-H319-H336
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P261-P264+P265-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P319-P337+P317-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Trimethoxymethane, also known as methylene trimethyl ether, is an organic compound with the molecular formula C5H12O3. It belongs to the class of ether compounds and features three methoxy (-OCH3) groups attached to a central methylene (-CH2-) carbon. The synthesis of trimethoxymethane dates back to the early 20th century when researchers began to explore the properties and potential applications of methoxy derivatives. Its discovery has since paved the way for various uses in the chemical industry and beyond.

The synthesis of trimethoxymethane typically involves the reaction of formaldehyde with methanol in the presence of a suitable acid catalyst. The process results in the formation of the ether compound, which can be further purified through distillation or chromatography. This simple synthetic pathway makes trimethoxymethane accessible for industrial applications, contributing to its growing popularity in various fields.

One of the primary applications of trimethoxymethane is as a solvent and reagent in organic synthesis. Due to its ether-like properties, it is an effective solvent for a wide range of organic compounds. The ability to dissolve both polar and nonpolar substances makes trimethoxymethane a versatile medium for chemical reactions, including those involving complex organic molecules. This solvent capability has led to its use in the pharmaceutical industry, where it aids in the formulation of drugs and the synthesis of active pharmaceutical ingredients (APIs).

In addition to its role as a solvent, trimethoxymethane has been utilized as a protective group in organic synthesis. The methoxy groups can temporarily protect reactive functional groups during chemical reactions, allowing for selective transformations. This feature is particularly valuable in multi-step synthesis processes, where maintaining the integrity of certain functional groups is crucial for achieving the desired product. Researchers have developed various methodologies that leverage the protective capabilities of trimethoxymethane, enhancing its utility in synthetic organic chemistry.

Trimethoxymethane has also garnered attention for its potential applications in the field of materials science. The compound can serve as a precursor for the synthesis of polymers and other materials with tailored properties. By incorporating trimethoxymethane into polymer matrices, researchers can influence the mechanical, thermal, and chemical resistance of the resulting materials. This versatility opens new avenues for the development of advanced materials suitable for diverse applications, including coatings, adhesives, and composites.

Furthermore, trimethoxymethane has shown promise in the field of green chemistry. Its ability to facilitate reactions in a mild and environmentally friendly manner aligns with the principles of sustainability and reduction of hazardous waste. Researchers are increasingly investigating trimethoxymethane as a solvent alternative in various chemical processes, aiming to minimize the environmental impact of synthetic chemistry.

Despite its numerous applications, safety considerations are essential when handling trimethoxymethane. The compound is classified as a flammable liquid, and proper laboratory practices should be followed to prevent accidents. Adequate ventilation, use of personal protective equipment, and adherence to safety protocols are crucial to mitigate any risks associated with its use.

In conclusion, trimethoxymethane is a versatile compound with significant applications in organic synthesis, materials science, and green chemistry. Its discovery has facilitated advancements in various chemical processes, making it a valuable asset in the pharmaceutical industry and beyond. As research continues to explore its properties and potential uses, trimethoxymethane may play a pivotal role in developing innovative solutions and sustainable practices across multiple fields.

References

2024. Reactions of phosphorus (IV) and orthocarboxylic acid esters with benzal and benzyl halides: pathways and catalysis. Russian Chemical Bulletin, 73(9).
DOI: 10.1007/s11172-024-4382-8

2022. First representative of phosphorylated formic acid hydrazides with three P-C bonds: synthesis and addition to the phosphorylated 4-methylenequinones. Russian Chemical Bulletin, 71(3).
DOI: 10.1007/s11172-022-3433-2

2022. Dimroth rearrangement "thiadiazole-triazole": synthesis and exploration of 3-sulfanyl-1,2,4-triazolium salts as NHC-proligands. Russian Chemical Bulletin, 71(5).
DOI: 10.1007/s11172-022-3501-7