24055-46-7

Usage

Uses

Used in Dye and Pigment Manufacturing:
2,3-DIMETHYL-1-NITRONAPHTHALENE is used as a key intermediate in the production of dyes and pigments, contributing to the coloration and stability of these products.
Used in Organic Synthesis:
2,3-DIMETHYL-1-NITRONAPHTHALENE is used as a precursor in the synthesis of other organic compounds, serving as a building block for more complex chemical structures in various industries.

InChI:InChI=1/C12H11NO2/c1-8-7-10-5-3-4-6-11(10)12(9(8)2)13(14)15/h3-7H,1-2H3

Upstream product

• 581-40-8 2,3-dimethylnaphthalene 

Downstream Products

• 81824-67-1 1-Amino-2,3-dimethylnaphthalin 

Relevant academic research and scientific papers

Highly Twisted N,N-Dialkylamines as a Design Strategy to Tune Simple Aromatic Hydrocarbons as Steric Environment-Sensitive Fluorophores

The steric-environment sensitivity of fluorescence of 9,10-bis(N,N-dialkylamino)anthracenes (BDAAs) was studied experimentally and theoretically. A new design strategy to tune simple aromatic hydrocarbons as efficient aggregation-induced emission (AIE) luminogens and molecular rotors is proposed. For a variety of BDAAs, prominent Stokes shifts and efficient solid-state fluorescence were observed. Calculations on BDAA-methyl suggested that in the ground state (S0) conformations, the pyramidal amine groups are highly twisted, so that their lone-pair orbitals cannot conjugate with the anthracene π orbitals. Fluorescence takes place from the S1 minima, in which one or both amine groups are planarized. The stability of the S1 excited state minima as well as destabilization of the S0 state is the origin of large Stokes shift. Experimental measurement of the nonadiabatic transition rate suggests that para disubstitution by dialkylamino (or strongly electron-donating) groups is a key for fast internal conversion. Minimum energy conical intersection (MECI) between S1 and S0 states was found to have a Dewar-benzene like structure. Although this can be reached efficiently in liquid phase for fast internal conversion, a large amplitude motion is required to reach this MECI, which is prohibited in the solid state and caused efficient AIE. This strategy is used to find experimentally that naphthalene analogues are also efficient AIE luminogens. The flexibility of alkyl chains on amino groups is also found to be important for allowed charge-transfer transition. Thus, three points [(1) highly twisted N,N-dialkylamines, (2) substitution at the para positions, (3) with flexible alkyl groups] were proposed for activation of small aromatic hydrocarbons.

Nitration of Reactive Aromatics via Elelctron Transfer. V. On the Reaction between Nitrogen Dioxide and the Radical Cation Hexafluorophosphates of Some Methyl-substituted Naphthalenes

The coupling reactions of series of methylnaphthalene radical cation hexafluorophosphates with nitrogen dioxide were studied in dichloromethane at low temperatures.Yields of nitro derivatives were generally higher with the β-methyl than with the α-methyl-substituted naphthalenes and the isomer distributions were different from those obtained in electrophilic aromatic nitration and nitrous acid catalyzed nitration.This confirm an earlier suggestion that the coupling reaction is not an elementary step of either nitration process.The high regioselectivity of the coupling reation can only partly be correlated with UHF spin densities.Pyrene+. hexafluorophosphate does not yield nitropyrenes upon treatment with nitrogen dioxide.This confirm earlier suggestions that only radical cations of aromatics with Eo values >= 1.7 V will take part in a successful (exergonic) coupling reaction with nitrogen dioxide.