41652-79-3

Usage

Classification

Aromatic amine

Common Uses

Manufacture of dyes, pigments, and industrial products

Physical Properties

Color: Pale yellow to brown
Odor: Slight amine odor

Toxicity

Considered to have low toxicity

Environmental Impact

Not expected to be harmful to the environment

Handling

Should be handled with care

Storage

Should be stored in a well-ventilated area

Upstream product

• 15316-91-3 N-allyl-o-toluidine 
• 7664-93-9 sulfuric acid 
• 95-53-4 o-toluidine 
• 1035570-51-4 2-(methoxymethyl)-6-methylaniline 
• 1826-67-1 vinyl magnesium bromide 
• 2622-05-1 allylmagnesium bromide 
• 74965-31-4 N-(tert-butoxycarbonyl)-o-toluidine 

Downstream Products

• 68461-08-5 2-Methyl-6-(1'-propenyl)anilin 
• 68460-57-1 N-(2-Allyl-6-methyl-phenyl)-2-chloro-N-methoxymethyl-acetamide 
• 863968-47-2 6-methyl-2-[(Z)-1-propenyl]aniline 
• 863968-48-3 6-methyl-2-[(E)-1-propenyl]aniline 
• 1431884-74-0 C₁₅H₁₇NO₂ 
• 1431971-98-0 C₁₅H₁₇NO 
• 106377-27-9 2,2,2-trichloro-N-o-tolylacetimidamide 

Relevant academic research and scientific papers

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

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.

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.).

Transposed Paternò-Büchi reaction

A complementary strategy of utilizing nπ? excited state of alkene instead of nππ? excited state of the carbonyl chromophore in a "transposed Paternò-Büchi" reaction is evaluated with atropisomeric enamides as the model system. Based on photophysical inves

Engaging electronic effects for atropselective [5+2]-photocycloaddition of maleimides

Atropisomeric maleimides were synthesized and subjected to atropselective [5+2]-photocycloaddition under direct irradiation to yield azepinone products with high enantio- (ee >98%) and diastereoselectivity (dr >98%). While the ee was dictated by the axial

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

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.

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.

Lewis acid catalyzed amino-Claisen rearrangement: A facile one pot synthesis of 2-allylarylamines from N-allylarylamines

Boron trifluoride-diethyl ether complex efficiently catalyzes a variety of amino-Claisen rearrangements of N-allylarylamines 1a-g to afford 2-allylarylamines 2a-g in moderate to good yields. N-allylarylamines having electron deficient substituents undergo

Proton catalyzed amino-Claisen rearrangement: A practical one step approach to the synthesis of 2-allylarylamines from N-allylarylamines

Proton catalyzed amino-Claisen rearrangement of N-allylarylamines (1a-h) afforded 2-al1y1arylamines (2a-h) respectively in moderate to good yields.