N,N-Dimethylformamide dimethyl acetal
[CAS# 4637-24-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: N,N-Dimethylformamide dimethyl acetal
• Synonyms: 1,1-Dimethoxytrimethylamine; N-Dimethoxymethyl-N,N-dimethylamine; DMF-DMA
• Molecular Formula: C₅H₁₃NO₂
• Molecular Weight: 119.16
• CAS Registry Number: 4637-24-5
• EC Number: 225-063-3
• SMILES: CN(C)C(OC)OC

Properties

• Density: 0.897
• Melting point: -85 °C
• Boiling point: 104-108 °C
• Refractive index: 1.3972
• Flash point: 7 °C
• Water solubility: hydrolysis

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H225-H302+H315+H317-H318-H319-H332-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H332
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H332

• Transport Information: UN 3271

Discovery and Applications

N,N-Dimethylformamide dimethyl acetal (DMFDMA) is an organic compound with the formula C5H13NO2. It was first synthesized in the mid-20th century as chemists explored the reactivity and applications of acetal derivatives of formamide. The compound is typically produced through the reaction of dimethylformamide (DMF) with methanol under acidic conditions. The discovery of DMFDMA offered chemists a versatile reagent for various organic transformations, particularly in the field of formylation and methylation reactions.

DMFDMA is widely used in organic synthesis as a formylating and methylating agent. Its reactivity makes it particularly useful for introducing formyl groups into organic molecules, a crucial step in the synthesis of many complex compounds. For example, DMFDMA can be used to convert amines into formamides, which are key intermediates in various chemical processes. Additionally, it can participate in the Vilsmeier-Haack reaction, forming valuable intermediates for further synthetic applications.

In the pharmaceutical industry, DMFDMA plays a crucial role in the synthesis of active pharmaceutical ingredients (APIs) and intermediates. Its ability to introduce formyl groups into compounds is essential for creating drug molecules with specific biological activities. For instance, it is used in the synthesis of certain antiviral and anticancer agents, where precise functionalization of the molecular structure is required.

DMFDMA is also utilized in the agrochemical sector to develop herbicides, insecticides, and fungicides. The compound's ability to facilitate the synthesis of complex molecules allows for the creation of agrochemicals that target specific pests and diseases

In materials science, DMFDMA is used in the synthesis of advanced materials, including polymers and resins. Its reactivity can introduce specific functional groups into polymer chains, enhancing properties such as thermal stability, chemical resistance, and mechanical strength. These materials are used in a variety of applications, including coatings, adhesives, and high-performance engineering plastics.

DMFDMA is widely used in academic and industrial research for studying new synthetic methodologies and reaction mechanisms. Researchers employ it as a reagent to explore novel chemical transformations and develop more efficient synthetic routes. Its role in formylation and methylation reactions provides valuable insights into the behavior of organic molecules and the development of innovative chemical processes.

Beyond its role in synthesis, DMFDMA is used in various industrial applications. Its ability to act as a solvent and a reagent in chemical manufacturing processes makes it valuable in the production of coatings, dyes, and other specialty chemicals.

References

2024. Heterocyclization reactions. Russian Journal of Organic Chemistry, 54(13).
DOI: 10.1134/s1070428023130031

2024. Synthesis of AZD7648. Chemical Papers, 78(5).
DOI: 10.1007/s11696-024-03306-8