75654-11-4

Basic information

• Product Name: 2,2,2-TRIMETHOXY-ACETAMIDE
• Synonyms: 2,2,2-TRIMETHOXY-ACETAMIDE
• CAS NO: 75654-11-4
• Molecular Formula: C₅H₁₁NO₄
• Molecular Weight: 149.15
• Mol File: 75654-11-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2,2-TRIMETHOXY-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIMETHOXY-ACETAMIDE(75654-11-4)
• EPA Substance Registry System: 2,2,2-TRIMETHOXY-ACETAMIDE(75654-11-4)

Safety Data

• Hazardous Substances Data: 75654-11-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,2,2-Trimethoxy-acetamide is used as a reagent in organic synthesis for the preparation of various chemical compounds. Its unique structure allows for versatile reactions and transformations, making it a valuable component in the synthesis of complex molecules.
Used in Pharmaceutical Preparation:
As a building block, 2,2,2-Trimethoxy-acetamide is utilized in the preparation of various pharmaceuticals. Its presence in the molecular structure can contribute to the development of new drugs with improved properties, such as increased efficacy or reduced side effects.
Used in Agrochemical Development:
2,2,2-Trimethoxy-acetamide is also used in the development of agrochemicals, which are chemicals designed to improve agricultural productivity. Its incorporation into these compounds can lead to the creation of more effective pesticides, herbicides, or other agricultural products.
Used in Materials Science:
In the field of materials science, 2,2,2-Trimethoxy-acetamide has been studied for its potential applications in the development of polymers and other advanced materials. Its unique properties may contribute to the creation of new materials with enhanced characteristics, such as improved strength, flexibility, or durability.
Used in Drug Candidate Research:
2,2,2-Trimethoxy-acetamide has been investigated for its biological activities and potential as a drug candidate. Although further research is needed to fully understand its pharmacological properties and potential therapeutic applications, its exploration in this area highlights the compound's versatility and potential for future medical advancements.

Upstream product

• 68714-36-3 trimethoxyacetonitrile 
• 98-86-2 acetophenone 
• 75654-15-8 N,N-Dimethyl-N'-(trimethoxyacetyl)formamidin 
• 100-63-0 phenylhydrazine 
• 105-56-6 ethyl 2-cyanoacetate 
• 109-77-3 malononitrile 

Relevant articles and documents

Orthoamides and iminium salts LXXVI [1]. A further contribution to the chemistry of trialkoxyacetonitriles

An improved procedure for the preparation of trimethoxyacetonitrile (3a) starting from trichlo-roacetonitrile and sodium methanolate is described. Carbanions, obtained by the action of sodium hydride on nitriles, ethyl acetate and methylketones, react with trialkoxyacetonitriles 3 to give α-imino-orthocarboxylic acid trialkylesters 12, 14 and 20, which form an equilibrium with the tautomeric enamines 13, 15 and 21. The enamines 21 react with N,N-dimethylformamide dimethylacetal (24) to give amidines 25 which are cyclized to pyridinium salts 28 and 29 on treatment with benzyl bromide and acetyl chloride, respectively. The reaction of the enaminonitrile 13a with the orthoamide derivative of phenylpropiolic acid 30 affords the pyridine-2-orthocarboxylic acid trimethylester 31. The N,O-protected 4-hydroxy-piperidine 35 can be deprotonated by means of sec-butyl lithium. The carbanions thus formed are trapped with D2O, dimethyl sulfate, phenylisocyanate, CO2, and dimethyl carbonate delivering the piperidine derivatives 37-41. The heterocyclic orthoester 43 can be prepared analogously from 35 and 3a. The piperidine derivatives 44, 46 and 47 are prepared from the N,O-protected piperidines 39 and 41.

Preparation and Reaction of Trimethoxyacetamide and Trimethoxyacetamide Derivates

Trimethoxyacetamide (2a) can be prepared from either trimethoxyacetonitrile (3) or from methyltrimethoxyacetate (1a).Similarly triethoxyacetamide can be obtained from 1b and ammonia.The synthesis of pure 1a is described.Hydrazine hydrate reacts with 1a to form trimethoxyacetohydrazide (6).The compounds 2a and 6 are formylated by tert-butoxy-N,N,N',N'-tetramethylmethanediamine ("aminal ester") at the NH2 group to furnish the formamidine 8 and the formamidrazone 9, respectively. 8 has also been prepared by reaction of N,N-dimethylformamide dimethylacetal with 2a.Reaction of 8 with phenylhydrazine affords the tetrazine 11.CH-acidic compounds such as malonodinitrile and ethyl cyanoacetate are formylated by 8 at the CH2 groups to yield the enamines 12a,b .