24331-71-3

Usage

Uses

Used in Organic Synthesis:
N,N-Dimethylpivalamide is used as a reagent in organic synthesis for the preparation of pharmaceuticals and agrochemicals. Its unique chemical properties make it a valuable component in the synthesis of various organic compounds.
Used in Polymer and Resin Stabilization:
N,N-Dimethylpivalamide is used as a stabilizer for polymers and resins, enhancing their durability and performance. Its ability to improve the stability of these materials makes it an essential ingredient in various industries.
Used in Coatings, Adhesives, and Personal Care Products:
N,N-Dimethylpivalamide is utilized as an ingredient in coatings, adhesives, and personal care products. Its low toxicity and compatibility with various materials make it a preferred choice for these applications, ensuring the safety and effectiveness of the final products.

InChI:InChI=1/C7H15NO/c1-7(2,3)6(9)8(4)5/h1-5H3

Upstream product

• 3282-30-2 pivaloyl chloride 
• 124-40-3 dimethyl amine 
• 74-83-9 methyl bromide 
• 21678-37-5 N,N,2-trimethylpropionamide 
• 52185-25-8 4,4-dimethyl-2-(3-trifluoromethyl-phenyl)-semicarbazide 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 25530-28-3 N,N,2,2-tetramethylpropanethioamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 1478-62-2 pivaloyl fluoride 
• 630-19-3 pivalaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 75-98-9 Trimethylacetic acid 
• 72286-65-8 W₂(CH₂CH₃)2(N(CH₃)2)4 

Downstream Products

• 25530-28-3 N,N,2,2-tetramethylpropanethioamide 
• 1639-66-3 sodium dioctyl sulfosuccinate 
• 26154-20-1 neopentyltrimethylammonium iodide 
• 5469-26-1 1-Bromopinacolon 
• 6625-74-7 N-pivaloylaniline 
• 1014613-61-6 4-bromo-2-(1,1-dimethylethyl)-1H-pyrrolo[2,3-b]pyridine 
• 53698-03-6 2-(dimethylamino)-3,3-dimethylbutanenitrile 
• 70785-32-9 N,N-dibenzyl-2,2-dimethylpropanethioamide 
• 69212-62-0 2,2-dimethyl-N-(thiazol-2-yl)-propionamide 
• 170959-10-1 2-iodo-pivaloylaminobenzene 
• 56619-94-4 4-methoxy-N-pivaloylaniline 
• 109902-33-2 N-2-chloropyrid-3-yl-trimethylacetamide 
• 86847-59-8 2-(pivaloylamino)pyridine 

Relevant academic research and scientific papers

INTERRELATIONS OF THE ENERGETICS OF AMIDES AND ALKENES: ENTHALPIES OF FORMATION OF N,N-DIMETHYL DERIVATIVES OF PIVALAMIDE, 1-ADAMANTYLCARBOXAMIDE AND BENZAMIDE, AND OF STYRENNE AND ITS α-, TRANS-β AND β,β-METHYLATED DERIVATIVES

The enthalpies of formation of the condensed phase and gaseous N,N-dimethyl derivatives of pivalamide, 1-adamantylcarboxamide and benzamide were determined by combustion calorimetry and the associated enthalpies of vaporization and sublimation.The enthalpies of formation of styrene and its α-, trans-β- and β,β-methylated derivatives were determined from measurements of their enthalpies of hydrogenation in dilute hydrocarbon solution.Strain and resonance effects of amides and alkenes are discussed in terms of the exo-/endothermicity of the following reactions: CH3CONH2(g)+RC(CH3)=CH2 -> (CH3)2C=CH2(g)+RCONH2(g), CH3CON(CH3)2(g)+RCH=C(CH3)2(g) -> CH3CH=C(CH3)2(g)+RCON(CH3)2(g) and in terms of the difference of enthalpies of formation of the isomeric (Z)- and (E)-RCH=CHCH3.

Direct amidation of acid fluorides using germanium amides

Amide functional groups are an essential linkage that are found in peptides, proteins, and pharmaceuticals and new methods are constantly being sought for their formation. Here, a new method for their preparation is presented where germanium amides Ph3GeNR2convert acid fluorides directly to amides. These germanium amides serve to abstract the fluorine atom of the acid fluoride and transfer their amide group -NR2to the carbonyl carbon, and so function as amidation reagents.

A scalable continuous photochemical process for the generation of aminopropylsulfones

An efficient continuous photochemical process is presented that delivers a series of novel γ-aminopropylsulfones via a tetrabutylammonium decatungstate (TBADT) catalysed HAT-process. Crucial to this success is the exploitation of a new high-power LED emitting at 365 nm that was found to be superior to an alternative medium-pressure Hg lamp. The resulting flow process enabled the scale-up of this transformation reaching throughputs of 20 mmol h-1 at substrate concentrations up to 500 mM. Additionally, the substrate scope of this transformation was evaluated demonstrating the straightforward incorporation of different amine substituents as well as alkyl appendages next to the sulfone moiety. It is anticipated that this methodology will allow for further exploitations of these underrepresented γ-aminopropylsulfone scaffolds in the future. This journal is

Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation

A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.

Amide-ligand-controlled highly para-selective arylation of monosubstituted simple arenes with arylboronic acids

Pd-catalyzed highly para-selective arylations of monosubstituted simple arenes with arylboronic acids to widely existed biaryls have been developed. Inspired by requisite amide-directing groups in reported selective oxidative couplings, amide ligands, especially DMF, are designed and found to be critical for the selectivity control in current arylations.

Easy access to amides through aldehydic C-H bond functionalization catalyzed by heterogeneous Co-based catalysts

A novel synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). The small Co nanoparticles embedded in the N-doped carbons were highly dispersed with an average size of ca. 7 nm. The Co@C-N materials exhibited significantly enhanced catalytic activity in the oxidative amidation of aldehydes in comparison to those of commercial sources. A series of amides can be easily obtained in good to excellent yields. It was found that the reaction proceeded via radicals under mild conditions, and the carbonyl group in the amide product was from the aldehyde. Moreover, the catalyst could be easily separated by using an external magnetic field and reused several times without significant loss in catalytic efficiency under the investigated conditions. (Chemical Equation Presented).

α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling

Pd(II)-catalyzed α-C(sp3)-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.

Bromination of enamines from tertiary amides using the petasis reagent: A convenient one-pot regioselective route to bromomethyl ketones

An original one-pot synthesis of bromomethyl ketones is achived using the Petasis reagent (dimethyltitanocene) as a key for enamine generation. Several amides were used to test the limits of the procedure by changing either the alkyl chain R or the amino portion of the starting materials. The enamines generated in situ were allowed to react with bromine at low temperature followed by hydrolysis to yield bromomethyl ketones in excellent yields (85 to 95%). Mechanistic details and optimum conditions for the reaction are briefly discussed. The present approach offers several advantages such as regioselectivity in enamine formation, good yields, mild reaction conditions, and ease of experimentation.

N-directed aliphatic C-H borylation using borenium cation equivalents

Highly electrophilic boron cations derived from hindered amine borane complexes have been shown to undergo intramolecular aliphatic C-H borylation.

Can relief of ring-strain in a cyclopropylmethyllithium drive the Brook rearrangement?

α-Cyclopropyl-α-trialkylsilyl alkoxides were formed either by addition of cyclopropyllithiums to acylsilanes or by addition of organolithiums to a cyclopropylformylsilane. [1,2]-Brook rearrangement led to α-silyloxy organolithiums which on warming underwent cyclopropane ring opening and [1,5]-retro-Brook rearrangement to yield γ-silyl ketones. Despite the favourability of the cyclopropane ring opening, the Brook rearrangement still required the presence of an anion stabilising group to proceed. β-Silylketones were similarly formed by Brook-retro-Brook rearrangement on warming acylsilanes with a vinyllithium.