875-79-6

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Dimethylindole is used as a building block for the preparation of 3-functionalized indoles, which are important in the development of pharmaceutical compounds with diverse biological activities.
Used in Organic Synthesis:
1,2-Dimethylindole is used as a building block for the preparation of carbazoles, a group of nitrogen-containing heterocyclic organic compounds with potential applications in various fields.
Used in Organic Synthesis:
1,2-Dimethylindole is used as a building block for the preparation of cyanoindoles, which are valuable intermediates in the synthesis of various organic compounds.
Used in Organic Synthesis:
1,2-Dimethylindole is used as a reactant for the preparation of trifluoromethylindoles, which are important intermediates in the synthesis of pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
1,2-Dimethylindole is used as a reactant for the preparation of potent antihyperlipidemic agents, which are compounds that help in reducing high levels of lipids in the blood.
Used in Organic Synthesis:
1,2-Dimethylindole is used as a building block in iso-Nazarov or Nazarov cyclizations, which are important reactions in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
1,2-Dimethylindole is used as a reactant for the preparation of GSK-3 inhibitors, which are compounds that target glycogen synthase kinase-3 and have potential applications in the treatment of various diseases.
Used in Organic Synthesis:
1,2-Dimethylindole is used as a building block for the preparation of carboxyindoles, which are valuable intermediates in the synthesis of various organic compounds.
Used in Agriculture:
1,2-Dimethylindole is used as a reactant for the preparation of plant growth promoters, which are compounds that enhance plant growth and development.
Used in Organic Synthesis:
1,2-Dimethylindole is used as a reactant for the preparation of tryptophan derivatives, which are important intermediates in the synthesis of various organic compounds and pharmaceuticals.

InChI:InChI=1/C10H11N/c1-8-7-9-5-3-4-6-10(9)11(8)2/h3-7H,1-2H3

Upstream product

• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 3741-86-4 acetone methylphenylhydrazone 
• 31399-19-6 1-(ethyl(phenyl)amino)propan-2-one 
• 4348-19-0 N-ethylaniline hydrochloride 
• 69887-86-1 1,2-dimethyl-3-nitro-pyridinium 
• 6407-34-7 methyl-1 ethylideneamine 
• 41652-73-7 N-Methyl-o-(prop-2-enyl)aniline 
• 78307-58-1 1-(2-Methylamino-phenyl)-propan-2-one 
• 141-78-6 ethyl acetate 
• 611-21-2 N,2-dimethylaniline 
• 6832-87-7 2-bromo-N-methylaniline 
• 67-64-1 acetone 
• 57-55-6 propylene glycol 
• 100-61-8 N-methylaniline 

Downstream Products

• 51226-47-2 1,2-dimethyl-5-nitro-1H-indole 
• 87401-40-9 1,2-dimethyl-octahydro-indole 
• 51072-84-5 1,2-dimethyl-1H-indole-3-carbonitrile 
• 33022-90-1 1-(1,2-dimethyl-1H-indol-3-yl)ethanone 
• 340169-30-4 1,2-dimethyl-3-(phenylthio)-1H-indole 

Relevant academic research and scientific papers

Mechanistic Studies of the Fischer Indole Reaction

Kinetic and solvent isotope effects were measured for the Fischer indole reactions of four hydrazones.Under neat acid conditions (5percent P2O5/MeSO3H) the KIE's ranged from 3.2 to 5.8, while the solvent isotope effects (kH/kD) ranged from 0.4 to 0.7.Under dilute acid conditions in sulfolane solvent, both isotope effects were near unity.The large kinetic isotope effect and large inverse solvent isotope effect, along with the observation that isotopic exchange occurs in the aromatic ring of the hydrazones, suggest that a preequilibrium protonation of the aromatic ring occurs followed by the rate-determining ene-hydrazine formation under the neat acid conditions.In contrast, under the dilute acid conditions, the lack of isotope effects and the lack of ring isotope exchange indicate that no ring protonation is occurring, that ene-hydrazine formation is no longer rate-determining, and that the rate-limiting step is now most likely the rearrangement.

Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes

The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

Synthesis of 3-halogenated 2,3′-biindoles by a copper-mediated 2,3-difunctionalization of indoles

A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles is described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Here the copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoids the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into molecules would offer great potential for further chemical transformations. This journal is

Facile C-S Bond Cleavage of Aryl Sulfoxides Promoted by Bronsted Acid

A method for the Bronsted acid promoted desulfination of aryl sulfoxides is presented. In the presence of a thiol, electron-rich sulfoxides undergo C-S bond cleavage to give the corresponding protodesulfinated arenes and disulfides.

Compound used as blue pressure-sensitive dye and preparation method and application thereof

The invention relates to a compound used as a blue pressure-sensitive dye, and the structural general formula of the compound is shown in the specification, in the formula, R1 is CH3, CH2CH3, CH2CH2CH3 or CH2CH2CH2CH3; and R2 is CH3 or CH2CH3. Three key intermediates including substituted indole, reactive hydrogen substituted m-aminophenol and chlorophthalic anhydride are adopted, and the target compound used as the blue pressure-sensitive dye is obtained through two-step condensation. Raw materials required for synthesis are easy to obtain, the conversion rate of each step in the synthesis process is high, and no complex purification procedure is needed in the intermediate process. The target compound is high in color rendering property, the molar absorption coefficient of the target compound reaches 1.8 times that of CVL, and the same color rendering effect of CVL can be achieved under the low pressure-sensitive dye using concentration.

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide

Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).

Method for preparing indole compound through air oxidation catalyzed by N-hydroxyphthalimide

The invention discloses a method for preparing an indole compound through non-transition metal catalyzed air oxidation. According to the method, the low-cost N-hydroxyphthalimide is used as a catalystand air is used as an oxidizing agent, wherein indoline compounds are oxidized in an organic solvent, and synthesis of the indoline compounds is achieved. The method has the advantages of simple reaction operation, low reaction cost, high yield, mild conditions, no heavy metal pollution and the like.