Trimethyl orthoacetate
[CAS# 1445-45-0]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: Trimethyl orthoacetate
• Synonyms: 1,1,1-Trimethoxyethane
• Molecular Formula: C₅H₁₂O₃
• Molecular Weight: 120.15
• CAS Registry Number: 1445-45-0
• EC Number: 215-892-9
• SMILES: CC(OC)(OC)OC

Properties

• Density: 0.944
• Boiling point: 107-109 °C
• Refractive index: 1.387-1.389
• Flash point: 16 °C
• Water solubility: HYDROLYSIS

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H317-H319
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264+P265-P272-P280-P302+P352-P303+P361+P353-P305+P351+P338-P321-P333+P317-P337+P317-P362+P364-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

by reacting methanol with orthoformic acid.

TMOA serves as a versatile reagent in organic synthesis, facilitating the preparation of a wide range of chemical compounds. It participates in numerous reactions, including esterifications, acylations, and nucleophilic substitutions, enabling the synthesis of complex molecules and fine chemicals used in pharmaceuticals, agrochemicals, and specialty chemicals.

TMOA functions as a solvent in various chemical processes and reactions. Its ability to dissolve a wide range of organic compounds makes it suitable for use in reaction mixtures, purification procedures, and formulation of chemical products. It serves as an alternative solvent to traditional polar solvents, offering advantages such as low volatility and high stability.

TMOA is utilized in the synthesis of polymers and polymer intermediates. It serves as a monomer or co-monomer in polymerization reactions, contributing to the formation of polymer chains with desired properties such as flexibility, toughness, and thermal stability.

TMOA and its derivatives serve as intermediates in the synthesis of pharmaceutical compounds. Their chemical reactivity allows for the introduction of functional groups necessary for the development of drug candidates targeting various therapeutic areas.

TMOA derivatives are used in the flavor and fragrance industry as aroma compounds and flavoring agents. Their distinct odor profiles contribute to the formulation of fragrances for perfumes, cosmetics, and household products, as well as flavorings for food and beverages.

TMOA derivatives find applications as fuel additives in the automotive and aviation industries. They improve fuel performance and stability by preventing oxidation, reducing engine deposits, and enhancing combustion efficiency.

References

2024-09-30. Enantioselective iridium-catalyzed allylic substitution with a Reformatsky reagent: direct construction of β-stereogenic homoallylic esters.
DOI: 10.1007/s11426-024-2284-x

2024-07. Naphthoquinoid pigments of sea urchins. Trimethyl orthoacetate as an effective reagent for O-methylation of β-OH groups of spinazarin, spinochromes D and E, and echinochrome A.
DOI: 10.1007/s11172-024-4328-1

2019-01. Trimethyl orthoacetate as a convenient reagent for selective methylation of β-OH groups of (poly)hydroxynaphthazarins.
DOI: 10.1007/s11172-019-2415-5