1113-57-1

Usage

Uses

Used in Food and Beverage Industry:
2-methylbutyramide is used as a flavoring agent for its nutty and creamy characteristics, enhancing the taste and aroma of various food and beverage products.
Used in Perfume and Cosmetic Industry:
2-methylbutyramide is used as a fragrance ingredient in perfumes and cosmetics, providing a pleasant scent that contributes to the overall sensory experience of these products.
Used in Pharmaceutical Industry:
2-methylbutyramide is used in the production of pharmaceuticals, likely due to its unique chemical properties and potential applications in drug development or formulation.
Used in Natural Product Enhancement:
2-methylbutyramide is found in natural sources such as cheese, meat, and butter, where it plays a key role in enhancing the overall sensory experience of these products by contributing to their distinct flavors and aromas.

InChI:InChI=1/C5H11NO/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H2,6,7)

Upstream product

• 18936-17-9 2-methylbutanenitrile 
• 5856-79-1 iso-butyl chloroformate 
• 108-12-3 isopentanoyl chloride 
• 319-78-8 isoleucine 
• 590-18-1 (Z)-2-Butene 
• 77287-34-4 formamide 
• 116-53-0 2-Methylbutanoic acid 
• 64-17-5 ethanol 
• 16668-14-7 4,4-dichloro-3-trichloromethyl-but-3-en-2-one 
• 33966-50-6 SEC-BUTYLAMINE 
• 97-61-0 2-Methylpentanoic acid 
• 106-98-9 1-butylene 
• 201230-82-2 carbon monoxide 
• 34907-98-7 1.1.3-Trichlor-butadien-(1.3)-carbonsaeure-⁽²⁾ 

Downstream Products

• 39076-02-3 Methyl N-sec-butylcarbamate 
• 18936-17-9 2-methylbutanenitrile 

Relevant academic research and scientific papers

Efficient heterogeneous hydroaminocarbonylation of olefins with ammonium chloride as amino source

An efficient protocol for heterogeneous hydroaminocarbonylation of olefins with ammonium chloride without addition of acid additive has been developed for the first time. We successfully synthesized the Pd@POPs-PPh3 catalyst through a solvothermal synthetic method. Under this heterogeneous catalytic system, C2-C6 olefins displayed good yields and TON, and a yield of 66% of propionamide and TON = 1400 were obtained under mild reaction conditions (403 K, Pethylene = 0.5 MPa, PCO = 2.5 MPa), which is a little higher than those in the homogeneous system. This catalytic system has the advantage of easy separation of product and catalyst, as well as good stability. Uniform dispersion of Pd active sites, strong coordination bond between P and Pd, high surface area, large pore volume and hierarchical porosity of Pd@POPs-PPh3 were confirmed by a series of characterizations, which is believed to be the keys for the good activity and stability of hydroaminocarbonylation reaction.

One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis

The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).

Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides

Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.

Effects of sulphur nutrition during potato cultivation on the formation of acrylamide and aroma compounds during cooking

Lack of sulphur nutrition during potato cultivation has been shown to have profound effects on tuber composition, affecting in particular the concentrations of free asparagine, other amino acids and sugars. This is important because free asparagine and sugars react at high temperatures to form acrylamide, a suspect carcinogen. Free amino acids and sugars also form a variety of other compounds associated with colour and flavour. In this study the volatile aroma compounds formed in potato flour heated at 180 °C for 20 min were compared for three varieties of potato grown, with and without sulphur fertiliser. Approximately 50 compounds were quantified in the headspace extracts of the heated flour, of which over 40 were affected by sulphur fertilisation and/or variety. Many of the 41 compounds found at higher concentrations in the sulphur-deficient flour were Strecker aldehydes and compounds formed from their condensation, whereas only one compound, benzaldehyde, behaved in the same way as did acrylamide and was found at higher concentrations in the sulphur-sufficient flour. The reasons for these effects are discussed.

Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues

Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA's clinical use is limited by two severe and lifethreatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of neuropathic pain and epilepsy. Among these, two amide and two urea derivatives of 1 showed the highest potency as antineuropathic pain compounds, with ED50 values of 49 and 51 mg/kg for the amides (19 and 20) and 49 and 74 mg/kg for the urea derivatives (29 and 33), respectively. 19, 20, and 29 were equipotent to gabapentin, a leading drug for the treatment of neuropathic pain. These data indicate strong potential for the above-mentioned novel compounds as candidates for future drug development for the treatment of neuropathic pain. 2009 American Chemical Society.

Synthesis of a diastereomeric mixture of (4R,5S,6E,14R)- and (4R,5S,6E,14S)-melithiazols G

A Wittig reaction between (+)-3 and the phosphoranylide derived from the bithiazole-type phosphonium iodide [(±)-4] using lithium bis(trimethylsilyl)amide afforded a diastereomeric mixture of the (+)-(4R,5S,6E,14R)- and (4R,5S,6E,14S)-melithiazols G (1), whose NMR spectral data were identical with those of the natural product (1). The antifungal activity of the synthetic diastereomeric mixture of melithiazols G (1) against the phytopathogenic fungus, Phytophthora capsici, was evaluated by using a paper disc assay method.

Analogs of isovaleramide, a pharmaceutical composition including the same, and a method of treating central nervous system conditions or diseases

An isovaleramide analog having at least one of an increased potency, an increased half-life, and an increased stability compared to isovaleramide. The isovaleramide analog is a cyclic analog or a noncyclic analog. The isovaleramide analog is formulated into a pharmaceutical composition. A method of treating a central nervous system condition or disease is also disclosed. The method comprises administering an isovaleramide analog to a patient suffering from the central nervous system condition or disease.

Lithium/DTBB-induced reduction of N-alkoxyamides and acyl azides

A series of N-alkoxyamides and N-methoxy-N-methylamides (Weinreb amides) have been subjected to dealkoxylation by reductive cleavage of the N-O bond with lithium powder and a catalytic amount of DTBB (10 mol%) at room temperature, leading to the corresponding amides. When the reaction is performed under reflux conditions, the corresponding alkanes, resulting from a formal deaminocarbonylation process, are obtained. This methodology applied to acyl azides furnished the corresponding primary amides.

Comparative studies on reactions of α,β- and β,γ-unsaturated amides and acids with nickel(0), palladium(0), and platinum(0) complexes. Preparation of new five- and six-membered nickel- and palladium-containing cyclic amide and ester complexes

Reactivities of α,β- and β,γ-unsaturated amides as well as acids with zerovalent nickel, palladium, and platinum complexes have been compared. α,β-Unsaturated amides and acids form nickel-containing five-membered cyclic amide and ester complexes, (PR3)NiCH2CH(CH3)CONH (PR3 = PCy3, PEt3, P(t-Bu)2Et, dppe, dppp, dppb) and (PCy3)NiCH2CH(CH3)COO. β,γ-Unsaturated amides and acids afford nickel-containing six-membered cyclic amide and ester complexes, (PCy3)NiCH2CH2CH2CONH and (PCy3)NiCH2CH2CH2COO, whereas the palladium-containing six-membered cyclic ester complex (PCy3)PdCH2CH2CH2COO has been obtained from Pd(PCy3)2 and 3-butenoic acid. Pt(cod)2 in the presence of PCy3 reacted with methacrylamides to give olefin-coordinated Pt(0) complexes, Pt(PCy3)(CH2=C(CH3)CONHR)2 (R = H, Ph), whereas the reaction with α,β- and β,γ-unsaturated acids gave oxidative-addition products of the acids, trans-PtH(O2CR)(PCy3)2 (R = -C(CH3)=CH2, -CH2CH=CH2). An X-ray crystallographic analysis of one of the five-membered nickel-containing cyclic amides [(PEt3)NiCH2CH(CH3)CONH]4, was carried out. A novel tetrameric cyclic structure containing a nickelacyclic amide framework linked through Ni-O bonds with adjacent amide carbonyl groups has been established. Treatment of the nickel- and palladium-containing five- and six-membered cyclic amide and ester complexes with CO liberated cyclic imides and anhydrides. Thermolysis and reactions of the nickelacyclic complexes with AlCl3 and maleic anhydride led to β-elimination reactions with release of unsaturated amides and acids.

Process for the preparation of formamide compounds

This invention relates to preparing formamide compounds in a process which comprises reacting an amine with a formylalkanolamine in the presence of carbon monoxide in which the mole ratio of amine to formylalkanolamine ranges from 0.2:1 to 5:1. The reaction is conducted at a temperature ranging from about 50° to 300° C. and a pressure ranging from about 100 to 10,000 psig. The amine employed in the reaction has the formula: STR1 wherein R' is hydrogen, an alkyl group of 1 to 10 carbon atoms, cyclohexyl, or --R"--O--R'", wherein R" is a divalent alkylene group of 2 to 4 carbon atoms and R'" is an alkyl group of 1 to 3 carbon atoms; and R is hydrogen or an alkyl group of 1 to 10 carbon atoms. The formylalkanolamine employed in the reaction has the formula: STR2 wherein R is an alkylene group of 1 to 3 carbon atoms, z is 0 or 1 and y is 1 or 2 and the sum of y and z is 2.