2,2-Diethoxyacetimidic acid methyl ester
[CAS# 76742-48-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2,2-Diethoxyacetimidic acid methyl ester
• Synonyms: 2,2-Diethoxyethanimidic acid methyl ester; Methyl 2,2-diethoxyacetimidate; Methyl diethoxyacetimidate
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.20
• CAS Registry Number: 76742-48-8
• EC Number: 831-116-7
• SMILES: CCOC(C(=N)OC)OCC

Properties

• Solubility: Sparingly soluble (19 g/L) (25 °C), Calc.^*
• Density: 1.01±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 159.0±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 50.0±30.1 °C (Calc.)^*
• Index of refraction: 1.422 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H227-H302-H315-H319-H335
• Safety Statements: P210-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Flammable liquids	Flam. Liq.	4	H227

Discovery and Applications

2,2-Diethoxyacetimidic acid methyl ester is an organic compound with a structure that includes both an ester and an imidic acid group. It is a derivative of acetimidic acid, with the presence of ethoxy groups (–OCH2CH3) at the 2-position of the acetimidic acid backbone. The compound's methyl ester functional group (–COOCH3) makes it suitable for a range of chemical reactions and synthetic applications.

This compound is primarily used in organic synthesis, where it can act as an intermediate for the preparation of other organic compounds. The ester group in 2,2-diethoxyacetimidic acid methyl ester is reactive and can undergo hydrolysis under acidic or basic conditions to regenerate the parent acid. This transformation is important in synthetic routes where the parent acid, 2,2-diethoxyacetimidic acid, is needed for further reactions.

The imidic acid group within the molecule suggests that 2,2-diethoxyacetimidic acid methyl ester can participate in reactions involving nucleophilic attack, as the imidic acid functionality is often reactive towards electrophiles. This reactivity makes the compound useful in the synthesis of various derivatives, particularly in the formation of more complex organic molecules. It can also be utilized as a precursor in the synthesis of biologically active molecules, where the imidic acid moiety may play a role in the final compound's properties.

Moreover, the presence of two ethoxy groups in the molecule makes it relatively hydrophobic, which could influence the solubility and reactivity of 2,2-diethoxyacetimidic acid methyl ester in different solvents or in biological systems. This property could make the compound a suitable candidate for research into drug delivery systems or as a building block for the synthesis of hydrophobic organic materials.

In summary, 2,2-diethoxyacetimidic acid methyl ester is a versatile compound in organic chemistry, acting as an intermediate in the synthesis of various compounds. Its reactive functional groups allow for a range of chemical transformations, making it useful in the preparation of more complex molecules. Though it does not have widespread industrial applications, it is valuable in research and synthetic chemistry.

References

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