17794-44-4

Usage

Uses

Used in the Food Industry:
N-Methylbutyramide is used as a flavoring agent for its ability to impart a unique taste to various food products. Its mild odor and pleasant flavor profile make it a valuable ingredient in enhancing the sensory experience of food items.
Used in the Perfumery Industry:
In the perfumery industry, N-Methylbutyramide is utilized as a fragrance ingredient to create distinct and appealing scents. Its mild odor contributes to the overall composition of perfumes, colognes, and other fragranced products, adding depth and complexity to the final scent.
Used in Pharmaceutical Synthesis:
N-Methylbutyramide serves as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its chemical properties make it a versatile building block for the development of new drugs and other medicinal agents.
Used in the Treatment of Neurological and Psychiatric Disorders:
N-Methylbutyramide has been studied for its potential use in the treatment of neurological and psychiatric disorders. Its ability to act as a GABA receptor modulator suggests that it may have therapeutic benefits in conditions such as epilepsy, anxiety, and depression. Further research is needed to fully understand its potential applications in this area.

InChI:InChI=1/C5H11NO/c1-3-4-5(7)6-2/h3-4H2,1-2H3,(H,6,7)

Upstream product

• 141-75-3 butyryl chloride 
• 74-89-5 methylamine 
• 109-74-0 propyl cyanide 
• 107-92-6 butyric acid 
• 541-35-5 butanamide 
• 1719-57-9 Chloro(chloromethyl)dimethylsilane 
• 19172-47-5 Lawessons reagent 
• 65753-90-4 N-methylbutyrohydroxamic acid 
• 593-51-1 methylamine hydrochloride 
• 109480-79-7 N-methyl-N-methoxycrotonamide 
• 109480-78-6 N-methoxy-N-methylbutanamide 
• 1343483-21-5 N-methyl-N-isopropoxybutyramide 
• 20605-40-7 thiobenzoylhydrazine 
• 96-31-1 N,N'-Dimethylurea 

Downstream Products

• 110-68-9 N-n-butyl-N-methylamine 
• 6973-82-6 N-methylbutylamine hydrochloride 
• 101463-66-5 N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]amino]thio]-N-methylbutanamide 
• 79242-10-7 benzoate-N-butyl-N-methylamide 
• 16395-81-6 N-methyl-N-nitrosobutyramide 

Relevant academic research and scientific papers

Amide proton exchange in micelles

Rate constants for acid- and base-catalyzed NH exchange of long-chain amides have been measured in cationic and anionic micelles and compared with NH exchange of model amides in aqueous solution. The data show that the rates can be strongly influenced by the electrostatic environment. Anionic micelles, where k(OH) decreases by a factor of about 2500 and where k(H) increases by a factor of about 100, show the largest effects. The effects of cationic micelles are smaller: a 30-fold decrease in k(H) (for ureas, or 6- fold for ordinary amides) and essentially no change in k(OH), which was unexpected. Other effects are negligible (less than a factor of about 2): counterion, nonionic surfactant, headgroup, chain length, etc. The data are discussed in terms of electrostatic effects, steric retardation, competition of counterions for the micellar surface, the Bronsted formulation of medium effects, charge exposure, and the nature of the transition state.

ATP Regeneration System in Chemoenzymatic Amide Bond Formation with Thermophilic CoA Ligase

CoA ligases are enzymes catalyzing the ATP-dependent addition of coenzyme A to carboxylic acids in two steps through an adenylate intermediate. This intermediate can be diverted by a nucleophilic non enzymatic addition of amine to get the corresponding amide for synthetic purposes. To this end, we selected thermophilic CoA ligases to study the conversion of various carboxylic acids into their amide counterparts. To limit the use of ATP, we implemented an ATP regeneration system combining polyphosphate kinase 2 (PPK2 Class III) and inorganic pyrophosphatase. Suitability of this system was illustrated by the lab-scale chemoenzymatic synthesis of N-methylbutyrylamide in 77 % yield using low enzyme loading and 5 % molar ATP.

Tuning the solid-state emission of the analogous GFP chromophore by varying alkyl chains in the imidazolinone ring

New analogues of green fluorescent protein (GFP) chromophore m GFP-C n (n = 1, 3, 5, 11) with alkyl chains of different lengths in the imidazolinone rings were synthesized and their crystal structures were determined. These GFP-like chromophores are all emissive in the solid state. And the solid-state emission quantum yields of increase by extending the lengths of alkyl chains, owing to the fact that the intermolecular pi-pi interactions are significantly weakened based on their crystal structures.

Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl 3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When β-substituted-α,β-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor.

Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity

To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two subsequent processes kT2 and kR2 were also measured. Correlation was also found for methine proton chemical shifts of N-isopropyl benzothiohydroxamic acids.

Towards supramolecular fixation of NOx gases: Encapsulated reagents for nitrosation

The use of simple calix[4]arenes for chemical conversion of NO2/ N2O4 gases is demonstrated in solution and in the solid state. Upon reacting with these gases, calixarenes 1 encapsulate nitrosonium (NO+) cations within their cavities with the formation of stable calixarene-NO+ complexes 2. These complexes act as encapsulated nitrosating reagents; cavity effects control their reactivity and selectivity. Complexes 2 were effectively used for nitrosation of secondary amides 5, including chiral derivatives. Unique size-shape selectivity was observed, allowing for exclusive nitrosation of less crowded N-Me amides 5a-e (up to 95% yields). Bulkier N-Alk (Alk > Me) substrates 5 did not react due to the hindered approach to the encapsulated NO+ reagents. Robust, silica gel based calixarene material 3 was prepared, which reversibly traps NO 2/ N2O4 with the formation of NO +-storing silica gel 4. With material 4, similar size-shape selectivity was observed for nitrosation. The N-Me-N-nitroso derivatives 6d,e were obtained with ～30% yields, while bulkier amides were nitrosated with much lower yields (+ species, which can be generated by a number of NOx gases, these supramolecular reagents and materials may be useful for NOx entrapment and separation in the environment and biomedical areas.

Encapsulated reagents for nitrosation

(Matrix presented) A novel class of stable, mild, and size-shape-selective nitrosating agents for secondary amides is introduced. These are based on reversible entrapment and release of reactive nitrosonium species by calix[4]arenes. The NO+ encapsulation controls the reaction selectivity.

Novel delta dicarbonyl compounds and methods for using the same

Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, sulfur or nitrogen attached to a methylene group, to which is further attached a sulfur, nitrogen or CH2 group. Methods of treating illnesses and conditions, such as cancer, hemological disorders, inherited metabolic disorders and others, using these compounds are also disclosed.

Novel delta dicarbonyl compounds and methods for using same

Amidomethyl esters, carbonylmercaptomethyl esters, keto-containing esters, amidomethyl thioesters, amidomethyl amides, and methylene dithioesters are disclosed. The novel compounds have two carbonyl groups connected by a linking moiety having an oxygen, s

Chemoselective methylation of amides and heterocycles using chloromethyldimethylsilyl chloride

The reaction of chloromethyldimethylsilyl chloride with an amide generates a pentacoordinate N-(amidomethyl)-halosilane that can be desilylated with cesium fluoride to give the N-methyl amide. This provides a selective method for the monoalkylation of amides in the presence of other, more nucleophilic groups. (C) 2000 Elsevier Science Ltd.