42498-33-9

Usage

Uses

Used in Pest Control Industry:
N-(1,1-Dimethylethyl)-3-methylbenzamide is used as an insect repellent for repelling a wide variety of pests, including mosquitoes, ticks, fleas, chiggers, and certain flies. It works by interfering with the insects' ability to detect carbon dioxide and lactic acid, which are the chemicals that attract them to humans. DEET has been widely used for decades and is considered safe when used according to label instructions.

InChI:InChI=1/C11H17N/c1-9-6-5-7-10(8-9)12-11(2,3)4/h5-8,12H,1-4H3

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 620-22-4 3-Methylbenzonitrile 
• 75-64-9 tert-butylamine 
• 1711-06-4 3-Methylbenzoyl chloride 
• 119072-55-8 tert-butylisonitrile 
• 108-38-3 m-xylene 
• 75-65-0 tert-butyl alcohol 
• 99-04-7 m-Toluic acid 
• 1712-87-4 bis(m-methylbenzoyl)-peroxide 
• 541-16-2 t-butyl malonate 
• 774-65-2 benzoic acid tert-butyl ester 
• 1634-04-4 tert-butyl methyl ether 
• 620-23-5 m-tolyl aldehyde 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 134312-83-7 N-tert-Butyl-5-methyl-2-methylselanyl-benzamide 
• 1404220-32-1 N-tert-butyl-5-methyl-2-(4-nitrophenylamino)benzamide 
• 1450753-71-5 N-tert-butyl-5-methyl-2-(4-nitrobenzamido)benzamide 
• 643-65-2 3-methyl benzophenone 

Relevant academic research and scientific papers

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Insight into Regioselective Control in Aerobic Oxidative C-H/C-H Coupling for C3-Arylation of Benzothiophenes: Toward Structurally Nontraditional OLED Materials

The installation of (benzo)thiophene-containing biaryls via coupling reactions has become a staple in designing photoelectric materials. Undeniably, C-H/C-H cross-coupling reactions between two (hetero)aromatics would be a shortcut toward these structural fragments. While more reliable cross-coupling technologies are well-established to provide C2-arylated (benzo)thiophenes, efficient methods that arylate the C3-position remain underdeveloped. Herein we provide insight into the factors that determine regioselectivity switching for these cross-coupling reactions. X-ray crystallographic analysis gives solid evidence for the key roles of triflate in regioselective dearomatization and acetate in base-assisted anti-β-deprotonated rearomatization. The first isolation and X-ray characterization of a medium-sized dearomatized cyclometalated adduct involving both substrates provide extra insight into aerobic oxidative Ar-H/Ar-H cross-coupling reactions. The mechanistic breakthrough incubates the first example, enabling C-H/C-H-type C3-arylation of benzothiophenes. Finally, this chemistry is used to design blue-emitting thermally activated delayed fluorescence (TADF) materials with a helicene conformation that exhibit a high maximum external quantum efficiency of 25.4% in OLED.

A convenient synthesis of N-tert-butyl amides by the reaction of di-tert-butyl dicarbonate and nitriles catalyzed by Cu(OTf)2

The utility of Cu(OTf)2 as the catalyst for the synthesis of a series of N-tert-butyl amides in excellent isolated yields via the reaction of nitriles (alkyl, aryl, benzyl, and furyl nitriles) with di-tert-butyl dicarbonate is described. Cu(OTf)2 is a highly stable and efficient catalyst for the present Ritter reaction under solvent-free conditions at room temperature.

Nickel-catalyzed aminocarbonylation of Aryl/Alkenyl/Allyl (pseudo)halides with isocyanides and H2O

Herein described is a nickel-catalyzed aminocarbonylation of aryl/alkenyl/allyl (pseudo)halides with isocyanides, providing aryl/alkenyl/allyl amides in 41% to 92% yields. Functional groups such as F, Cl, OMe, and heteroaromatic rings are compatible in the reaction. A Ni(0)/Ni(II) catalytic cycle is proposed based on preliminary experiments and previous literature. The reaction features readily available nickel salt, broad functional group tolerance, and simple reaction conditions.

Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol

The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.

Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles

Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO3H)][OTf] (neat or with [B

An efficient synthesis of N-tert-butyl amides by the reaction of tert-butyl benzoate with nitriles catalyzed by Zn(ClO4)2·6H2O

An efficient, mild and inexpensive synthesis of N-tert-butyl amides from the reaction of nitriles (aryl, benzyl and sec-alkyl nitriles) with tert-butyl benzoate catalyzed by the employment of 2?mol% Zn(ClO4)2·6H2O at 50?°C

An efficient transformation of methyl ethers and nitriles to amides catalyzed by Iron(III) perchlorate hydrate

An efficient and inexpensive synthesis of N-substituted amides from the reaction of nitriles with methyl ethers catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter Reaction under solvent-free conditions. A range of methyl ethers (benzyl, sec-alkyl and tert-butyl ethers) were reacted with nitriles to provide the corresponding amides in high–excellent yields.