55586-68-0

Usage

Uses

Used in Organic Synthesis:
4-DIETHYLAMINO-2-METHOXY-BENZALDEHYDE is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of a wide range of organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-DIETHYLAMINO-2-METHOXY-BENZALDEHYDE is utilized as a building block in the development of new medications, contributing to the synthesis of active pharmaceutical ingredients.
Used in Fragrance Industry:
4-DIETHYLAMINO-2-METHOXY-BENZALDEHYDE is employed as a key component in the production of fragrances, capitalizing on its floral scent to enhance the aroma of various perfumes and scented products.
Used in Dye and Pigment Manufacturing:
4-DIETHYLAMINO-2-METHOXY-BENZALDEHYDE is also used in the manufacturing of dyes and pigments, where its unique properties contribute to the coloration and stability of these products in different applications.

InChI:InChI=1/C12H17NO2/c1-4-13(5-2)11-7-6-10(9-14)12(8-11)15-3/h6-9H,4-5H2,1-3H3

Upstream product

• 450-83-9 4-fluoro-2-methoxybenzaldehyde 
• 109-89-7 diethylamine 
• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 

Downstream Products

• 753006-62-1 1-(4-diethylamino-2-methoxyphenyl)ethanol 
• 1268353-63-4 C₂₈H₃₄N₆O₂ 

Relevant academic research and scientific papers

Triphenylamine derived coumarin chalcones and their red emitting OBO difluoride complexes: Synthesis, photophysical and NLO property study

The auxiliary methoxy aided triphenylamine donors derived coumarin chalcones and their OBO complexes with branched donor-pi-acceptor systems are synthesized and characterized. Their photophysical properties are extensively studied in solvents of different polarity. They show strong emission solvatochromism and have quantum yields up to 0.87. The BF2-complexation of coumarin chalcones enhanced the quantum efficiency by approximately 1.4 times compared to the uncomplexed chalcones. Frontier molecular orbital analysis and Generalised Mulliken Hush analysis revealed a strong intramolecular charge transfer character of these chromophores. The first, second and third order polarizability of these chromophores are evaluated by the solvatochromic method and supported by Density Functional Theory calculations using CAM-B3LYP/6-31g(d) method. The third order nonlinear optical susceptibilities of these chromophores obtained by Z-scan analysis showed very less values of the imaginary part. Replacement of N-ethyl donors by aryl amine groups provided branched push-pull systems with enhanced thermal stability and nonlinear optical response.

X-ray structurally characterized quinoline based fluorescent probes for pH sensing: Application in intracellular pH imaging; DFT calculations and fluorescent labelling

Quinoline based fluorescent probes QNOH-MO and QNOH-OME were synthesized, and their photo-physical properties were carefully investigated. The probes were well characterized by 1H-NMR, 13C-NMR, ESI-MS, and single-crystal X-ray structure analysis. QNOH-MO and QNOH-OME can identify small changes in pH by colorimetric and fluorescence methods. In low pH range, these probes display a red fluorescence in both live and fixed cells. However, with increasing pH, the observed red fluorescence decreased with a simultaneous increase in green fluorescence. The pH-dependent switching from red to green fluorescence is well supported by theoretical calculations and 1H NMR titration experiments. Furthermore, the ability of these probes to image pH changes in live cells was also scrutinized. Moreover, QNOH-OME was successfully utilized for fluorescent labelling of cholesterol molecule which is an important component of biological membranes and is used in the liposomal formulation for drug delivery applications. Additionally, QNOH-MO was quaternized to induce an intrinsic cationic property to the molecule. The cationic probe QNOH-MO-CA exhibited improved water solubility and pH sensing efficiency.

A novel mitochondria-targeted ratiometric fluorescent probe for endogenous sulfur dioxide derivatives as a cancer-detecting tool

A new mitochondria-targeted fluorescent probe RBC, constructed using a coumarin moiety which was selected as the donor and a benzothiazole derivative as the acceptor, for SO2 derivatives (HSO3-/SO32-) was presented. The probe designed on a new FRET platform showed high selectivity and a low detection limit. Importantly, the probe could respond to HSO3-/SO32- within 35 s. Furthermore, the probe could target mitochondria and was successfully used for fluorescence imaging of endogenous bisulfite in HepG2 with low cytotoxicity, which significantly assisted in cancer diagnosis. This journal is

Synthesis of novel colorants for DSSC to study effect of alkyl chain length alteration of auxiliary donor on light to current conversion efficiency

Five (MA1-MA5) hemicyanine based sensitizer having N, N-diethyl aniline as a primary donor and hydroxy or alkoxy as an auxiliary donor have been synthesized to establish a correlation between amphiphilic nature of the sensitizer and charge recombination. A strong electron withdrawing 3-(carboxymethyl)-2-methylbenzo[d]thiazol-3-ium bromide has been explored as an acceptor. All the dyes were characterized by 1H-NMR, 13C-NMR and CHN analysis. The photophysical properties of these dyes were recorded in seven different solvents which do not show any significant impact on absorption and emission maxima while molar absorptivity coefficient decreases with increase in alkyl chain length. These dyes show very poor emission in all the solvents. Nano-crystalline mesoporous TiO2 based dye-sensitized solar cells were fabricated using MA1 to MA5 sensitizers to evaluate their photovoltaic performance. MA5 having six carbon alkyl chain shows maximum efficiency of 4.97% while MA1 without any alkyl chain shows the lowest efficiency of 3.40%. As the length of alkyl chain increase efficiency increase due to increment in short circuit current (Jsc) and retardation in the recombination process. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) were explored to obtain vertical excitation, HOMO-LUMO energy and electron density distribution.

PHOTOINDUCED ELECTRON TRANSFER VOLTAGE-SENSITIVE COMPOUNDS

The disclosure provides methods to synthesize photoinduced electron transfer voltage-sensitive compounds, the compounds made therefrom, and uses of the compounds thereof.

Chemical tweaking of a non-fluorescent GFP chromophore to a highly fluorescent coumarinic fluorophore: Application towards photo-uncaging and stem cell imaging

Three step chemical tweaking of nonfluorescent parent GFP chromophore has yielded a three hundred times as bright coumarinic fluorophore. A fluorogenic compound has been prepared which after photo-uncaging yields the same highly bright fluorophore that could be used for live stem cell imaging.

Effect of phenyl ring substitution on J-aggregate formation ability of novel bisazomethine dyes in vapour-deposited films

Bisazomethine dyes, which are synthesized using diaminomaleonitrile and aminobenzaldehydes, exhibit red fluorescence in solution and in the solid state. Several bisazomethine dyes are known to form J-aggregates in vapour-deposited films. In this work, novel bisazomethine dyes were synthesized and the effect of phenyl ring substitution on the J-aggregate formation in vapour-deposited films was examined. The optical properties of the dyes were examined in solution and in the solid state through molecular orbital calculations. Four derivatives were found to form J-aggregates in vapour-deposited films as determined from the shape of the spectrum and the absorption edge.

Tuning excited-state charge/proton transfer coupled reaction via the dipolar functionality

Based on design and synthesis of I, II, and III, we demonstrate an ingenious approach to fine-tuning the excited-state intramolecular charge transfer (ESICT) coupled excited-state intramolecular proton transfer (ESIPT) reaction via the dipolar functionality of the molecular framework. Both I and II exhibit remarkable dual emission due to the different solvent-polarity environment between ESICT and ESIPT states, while the interplay of two charge-transfer entities in III leads to ESIPT decoupling from the solvent-polarity effect, resulting in a unique proton-transfer tautomer emission. The results make further rational design of the ESICT/ESIPT coupled systems feasible simply by tuning the net dipolar effect. Accordingly, systematic investigation of the correlation in regards to the difference in dipolar vectors between ESICT and ESIPT versus solvent-polarity induced barriers becomes possible.

3-(substituted phenyl)phthalides

Process comprises the combination of the three steps of condensing 3-N(R)2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R)2 phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(α-Y-α-Z)methyl-4-X-5-N(R)2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R)2 phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R1 -3-R2 -2-R1 -phenyl, 1-R5 -2-R6 -5/6-R4 -3-indolyl, 9-R7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R1 -3-R2 -2-R1 -phenyl, 1-R5 -2-R6 -5/6-R4 -3-indolyl or 1-R8 -2-pyrrolyl which are useful as colorless precursor color formers in carbonless duplicating and in thermal marking systems. The intermediates, 3-Y-5-X-6-N(R)2 phthalides (II) and 2-(α-Y-α-Z)methyl-4-X-5-N(R)2 benzoic acids (III) also have utility as colorless precursor color formers in carbonless duplicating and thermal marking systems.

Novel compounds, processes and marking systems

Mono and bis substituted (arylsulfonyl)alkanes useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of the appropriate aldehyde or dialdehyde with the appropriate aryl or heterocyclic moiety and the appropriate phenylsulfinic acid in the presence of a catalyst.