15316-91-3

Usage

Uses

Used in Agrochemicals Production:
N-Allyl-O-toluidine is utilized as a key intermediate in the synthesis of various agrochemicals, contributing to the development of effective pest control agents and crop protection products.
Used in Pharmaceuticals Production:
N-ALLYL-O-TOLUIDINE serves as an essential building block in the creation of pharmaceuticals, playing a crucial role in the formulation of medications aimed at treating various health conditions.
Used in Rubber Accelerator Chemicals Production:
N-Allyl-O-toluidine is employed as a vital component in the production of rubber accelerators, which are used to enhance the curing process and improve the physical properties of rubber products.
Used in Dyes and Pigments Synthesis:
N-ALLYL-O-TOLUIDINE is also used in the synthesis of dyes and pigments, finding applications in various industries such as textiles, plastics, and printing inks, where its color-producing properties are harnessed to create a wide range of hues and shades.

InChI:InChI=1/C10H13N/c1-3-8-11-10-7-5-4-6-9(10)2/h3-7,11H,1,8H2,2H3

Upstream product

• 88-72-2 1-methyl-2-nitrobenzene 
• 2622-05-1 allylmagnesium bromide 
• 106-95-6 allyl bromide 
• 95-53-4 o-toluidine 
• 102-70-5 Triallylamine 
• 53443-78-0 2-methyl-N-prop-2-yn-1-yl-benzenamine 
• 107-18-6 allyl alcohol 
• 74965-31-4 N-(tert-butoxycarbonyl)-o-toluidine 

Downstream Products

• 57375-56-1 N-Ethoxycarbonyl-3-(N-allyl-o-tolylcarbamoyloxy)anilin 
• 67103-24-6 C₂₁H₂₀N₂O₄ 
• 41378-30-7 1-(2-methylphenyl)pyrrolidine 
• 83627-55-8 2-methyl-N-propylaniline 
• 41652-78-2 2,7-dimethyl-2,3-dihydro-indole 
• 41652-79-3 2-methyl-6-(prop-2-en-1-yl)aniline 
• 1431884-74-0 C₁₅H₁₇NO₂ 
• 1431971-98-0 C₁₅H₁₇NO 
• 1257292-13-9 N-(2-allyl-6-methylphenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Ruthenium-catalyzed synthesis of 2-ethyl-3-methylquinolines from anilines and triallylamine

Anilines react with triallylamine in dioxane at 180°C in the presence of a catalytic amount of ruthenium chloride and triphenylphosphine together with tin(II) chloride dihydrate to afford the corresponding 2-ethyl-3- methylquinolines in good yields.

Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor

We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.

Copper(ii)-hydroxide facilitated C-C bond formation: The carboxamido pyridine system: Versus the methylimino pyridine system

A copper(ii)-hydroxide-induced carbon-carbon bond formation reaction is explored with the synthesis of an asymmetric carboxamido-methylimino pyridine Cu(i) complex of [CuI(py(N-CO)(NC-C)ph2Me2)2]- (12). Two imine-methyl groups are coupled to form a bridge

Indole compound and synthesizing and application methods thereof

The invention relates to an indole compound and synthesizing and application methods thereof. The indole compound is prepared by selecting specific substituent groups. Experiments find that the indolecompound can achieve good inhibiting effects on prostatic cancer, good in drug-resistance-proofness and low in side effects when applied as an anti-cancer drug; besides, the synthesizing method of the indole compound comprises subjecting a compound with the structure shown as the formula (II), palladium acetate, benzoquinones and organic acids to reaction in solvent to obtain the indole compoundwith the structure shown as the formula (I). Experiment results show that the synthesizing method of the indole compound is low in requirements on substrate and high in product yield.

One-pot Construction of Difluorinated Pyrrolizidine and Indolizidine Scaffolds via Copper-Catalyzed Radical Cascade Annulation

A convenient approach to the synthesis of diverse difluorinated nitrogen-containing polycycles via a copper-catalyzed radical cascade annulation of amine-containing olefins and ethyl bromodifluoroacetate was developed. Three new bonds, including a Csp3 ?CF2 and two C?N bonds, are forged simultaneously in this strategy. Through this strategy, a series of difluorinated pyrrolizidine and indolizidine derivatives have been conveniently synthesized in good yields. (Figure presented.).

Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines

A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product. This journal is

Pentacoordinated Carboxylate π-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols

Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2] and 1,1′-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η3-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.

Light-induced stereospecific intramolecular [2+2]-cycloaddition of atropisomeric 3,4-dihydro-2-pyridones

Atropisomeric 3,4-dihydro-2-pyridones undergo stereospecific [2+2]-photocycloaddition in solution with high stereoselectivity (ee > 98% and de > 96%) in the product. The chiral transfer during phototransformation was rationalized based on the stability/reactivity of the biradical.

An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis

The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.

Efficient regio- And stereoselective formation of azocan-2-ones via 8-endo cyclization of α-carbamoyl radicals

The iodine-atom-transfer 8-endo cyclization of α-carbamoyl radicals was investigated experimentally and theoretically. With the aid of Mg(CIO 4)2 and a bis(oxazoline) ligand, N- ethoxycarbonylsubstituted N-(pent-4-enyl)-2-iodoalkanamides underwent 8-endo cyclization leading to the formation of only the corresponding 3,5-trans-substituted azocan-2-ones in excellent yields. Similarly, the BF 3·OEt2/H2O-promoted reactions of N-ethoxycarbonyl-N-(2-allylaryl)-2-iodoalkanamides afforded exclusively the benzazocanone products with a 3,5-cis configuration in high yields. The bidentate chelation of substrate radicals not only significantly improved the efficiency of cyclization but also resulted in the change of stereochemistry of azocanone products from 3,8-iransto 3,8-cis. Theoretical calculations at the UB3LYP/6-31G* level revealed that the cyclization of N-carbonyl- substituted α-carbamoyl radicals occurs via the E-conformational transition states without the presence of a Lewis acid. On the other hand, the cyclization proceeds via the Z-conformational transition states when the substrates form the bidentate chelation with a Lewis acid. In both cases, the 8-endo cyclization is always fundamentally preferred over the corresponding 7-exo cyclization. The complexed radicals having the more rigid conformations also allow the better stereochemical control in the iodine-atom-abstraction step. To further understand the reactivity of a-carbamoyl radicals, the competition between the 8-endo and 5-exo cyclization was also studied. The results demonstrated that the 8-endo cyclization is of comparable rate to the corresponding 5-exo cyclization for a-carbamoyl radicals with fixed Z-conformational transition states. As a comparison, the 8-endo mode is fundamentally preferred over the 5-exo mode in the cyclization of NH-amide substrates because the latter requires the Z-conformational transition states, whereas the former proceeds via the more stable E-conformational transition states.