21436-98-6

Usage

Uses

Used in Chemical Synthesis:
2,6-Dimethylaniline hydrochloride is used as a starting material for the preparation of 2,6-dimethylphenyl isocyanate via phosgenation. This isocyanate compound is an important intermediate in the production of various chemicals, including polyurethanes, which are widely used in the manufacturing of flexible and rigid foams, adhesives, coatings, and elastomers.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-dimethylaniline hydrochloride may be utilized as an intermediate for the synthesis of various pharmaceutical compounds. Its reactivity and structural properties make it a valuable building block for the development of new drugs and therapeutic agents.
Used in Dye and Pigment Industry:
2,6-Dimethylaniline hydrochloride can also be used in the dye and pigment industry for the production of organic dyes and pigments. Its chemical structure allows for the creation of a range of colors and hues, which can be applied in various applications such as textiles, plastics, and printing inks.
Used in Laboratory Research:
Due to its reactivity and unique chemical properties, 2,6-dimethylaniline hydrochloride is often used in laboratory research for the synthesis of various organic compounds and the study of chemical reactions. It serves as a valuable tool for chemists and researchers in understanding the behavior of similar compounds and developing new synthetic methods.

InChI:InChI=1/C8H11N.ClH/c1-6-4-3-5-7(2)8(6)9;/h3-5H,9H2,1-2H3;1H

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 
• 925-90-6 ethylmagnesium bromide 
• 118968-29-9 Re(N-2,6-C₆H₃Me₂)3(CH₂t-Bu) 
• 628-13-7 pyridine hydrochloride 
• 16687-12-0 trimethylsilylperrhenate 
• 28556-81-2 2,6-dimethylphenylisocyanate 
• 81-20-9 2,6-dimethylnitrobenzene 

Downstream Products

• 103994-80-5 3-[(2,6-Dimethyl-phenylamino)-methyl]-5-pyridin-4-yl-3H-[1,3,4]oxadiazole-2-thione; hydrochloride 
• 122456-50-2 1-(2.6-dimethylphenyl)-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline 
• 88366-21-6 3-(2,6-Dimethylphenyl)-3,7-dihydro-2,5-dimethyl-4H-pyrrolo<2,3-d>pyrimidin-4-imine 
• 42014-61-9 4-Cyclohexyl-2,6-dimethylanilin 
• 54810-82-1 3,5-dimethyl-[1,1'-biphenyl]-4-amine 
• 1127647-92-0 N,N′-bis(2,6-dimethylphenyl)pyridine-2,6-diamine 
• 1423129-34-3 C₃₁H₃₄N₄ 
• 1423129-45-6 C₄₃H₆₃N₄OSi₂Y 
• 1423129-46-7 C₄₉H₅₇N₆Y 
• 1423129-36-5 C₅₇H₅₁BF₁₅N₄OSiY 
• 1423129-35-4 C₃₉H₅₁N₄OSiY 
• 1423129-39-8 C₅₀H₅₆N₆PY 
• 4102-53-8 4-iodo-2,6-dimethylaniline 
• 159267-27-3 2,6-dimethylanilinium trichlorostannate(II) 

Relevant academic research and scientific papers

High-throughput approach for the identification of anilinium-based ionic liquids that are suitable for electropolymerisation

We report the synthesis of new protic ionic liquids (PILs) based on aniline derivatives and the use of high-throughput (HT) techniques to screen possible candidates. In this work, a simple HT method was applied to rapidly screen different aniline derivatives against different acids in order to identify possible combinations that produce PILs. This was followed by repeating the HT process with a Chemspeed robotic synthesis platform for more accurate results. One of the successful combinations were then chosen to be synthesised on a larger scale for further analysis. The new PILs are of interest to the fields of ionic liquids, energy storage and especially, conducting polymers as they serve as solvents, electrolytes and monomers at the same time for possible electropolymerisation (i.e. a self-contained polymer precursor).

Mild N-deacylation of secondary amides by alkylation with organocerium reagents

Secondary amides are a class of highly stable compounds serving as versatile starting materials, intermediates and directing groups (amido groups) in organic synthesis. The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis. Here, we report a protocol for the deacylation of secondary amides and isolation of amines. The method is based on the activation of amides with Tf2O, followed by addition of organocerium reagents, and acidic work-up. The reaction proceeded under mild conditions and afforded the corresponding amines, isolated as their hydrochloride salts, in good yields. In combination with the C-H activation functionalization methodology, the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

Steric hindrance as a key factor on proton transfer in the σ-adduct forming reactions of o-substituted anilines with 1,3,5-trinitrobenzene in dimethylsulfoxide

Kinetic and equilibrium studies are reported of the reactions of 1,3,5-trinitrobenzene (TNB) with a series of o-substituted anilines in dimethyl sulfoxide (DMSO) in the presence of 1,4-diazabicyclo[2.2.2.]octane (DABCO). The pKa values in DMSO for the aniline derivatives were measured using the proton-transfer equilibrium with 2,4-dinitrophenol. Kinetic studies are compatible with a two-step process involving initial nucleophilic attack on TNB by amine to give a zwitterionic intermediate which may transfer an acidic proton to DABCO to yield the anionic product. The results indicate steric hindrance to proton transfer in reactions involving 2,6-disubstituted anilines.

Synthesis of primary amines by the electrophilic amination of Grignard reagents with 1,3-dioxolan-2-one O-sulfonyloxime

(Chemical equation presented) Primary amines are prepared by the electrophilic amination of Grignard reagents with 4,4,5,5-tetramethyl-1,3- dioxolan-2-one O-phenylsulfonyloxime and the acidic hydrolysis of the resulting imines.