27913-86-6

Basic information

• Product Name: 4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde
• Synonyms: 4-[BIS-(2-HYDROXY-ETHYL)-AMINO]-BENZALDEHYDE;4-[N,N-BIS(2-HYDROXYETHYL)AMINO]BENZALDEHYDE;4-(N,N-BIS(2-HYDROXYETHYL)AMINO)BENZALD&;Methyl 2-acetylcaprylate;Benzaldehyde,4-[bis(2-hydroxyethyl)aMino]-;4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde 95%
• CAS NO: 27913-86-6
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.24
• Product Categories: Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 27913-86-6.mol

Chemical Properties

• Melting Point: 55-62 °C(lit.)
• Boiling Point: 433.42 °C at 760 mmHg
• Flash Point: 215.925 °C
• Appearance: light yellow powder
• Density: 1.252 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.21±0.10(Predicted)
• CAS DataBase Reference: 4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde(27913-86-6)
• EPA Substance Registry System: 4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde(27913-86-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-43
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 27913-86-6(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde is used as a cross-linking agent in the production of acrylic-based polymers. Its role in this application is to facilitate the formation of a three-dimensional network within the polymer matrix, enhancing the material's mechanical properties and stability.
Used in Metalworking Fluids:
In the metalworking industry, 4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde serves as a corrosion inhibitor. It helps to prevent the oxidation and degradation of metal surfaces when they come into contact with the fluids used in machining processes, thereby extending the life of the machinery and improving the quality of the finished products.
Used in Biomedical Research:
4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde is studied for its potential anti-tumor and anti-inflammatory properties. Its unique chemical structure allows it to interact with biological systems in ways that may inhibit tumor growth and reduce inflammation, making it a promising candidate for further research and development in the field of medicine.
Used in Pharmaceutical Development:
Given its potential therapeutic effects, 4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde is also considered in the development of pharmaceuticals. Its application in this industry is as a compound with possible anti-tumor and anti-inflammatory capabilities, which could lead to the creation of new drugs for the treatment of various diseases.

InChI:InChI=1/C11H15NO3/c13-7-5-12(6-8-14)11-3-1-10(9-15)2-4-11/h1-4,9,13-14H,5-8H2

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 83772-59-2 4-<4-benzylidene>-4'-N,N-dimethylaminoaniline 
• 41313-77-3 4-(bis(2-acetoxyethyl)amino)benzaldehyde 
• 120-07-0 2,2'-(phenylimino)bis[ethanol] 
• 68-12-2 N,N-dimethyl-formamide 
• 19249-34-4 bis(2-acetoxyethyl)aniline 
• 62-53-3 aniline 

Downstream Products

• 90120-66-4 5-<4-benzylidene>imidazolidine-2,4-dione 
• 90102-89-9 5-<4-benzylidene>-2-thioxo-4-thiazolidinone 
• 119438-04-9 DCM-OH 
• 146224-34-2 2-{2-[1-{4-[Bis-(2-hydroxy-ethyl)-amino]-phenyl}-meth-(Z)-ylidene]-3-oxo-indan-1-ylidene}-malononitrile 
• 83772-60-5 4-benzylidene-α-naphthylamine 
• 146224-36-4 2-((2-Hydroxy-ethyl)-{4-[(E)-2-(4-methanesulfonyl-phenyl)-vinyl]-phenyl}-amino)-ethanol 
• 146224-35-3 2-[[4-(Diphenyl-hydrazonomethyl)-phenyl]-(2-hydroxy-ethyl)-amino]-ethanol 
• 213817-46-0 4-{bis[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}benzaldehyde 
• 41313-77-3 4-(bis(2-acetoxyethyl)amino)benzaldehyde 
• 866122-74-9 C₅₈H₉₀Br₂N₂O₁₆ 
• 83772-61-6 4-benzyl-α-naphthylamine 

Relevant articles and documents

Synthesis and characterization of triple-azacrown ethers containing fluorene-cored derivatives: Application as electron injection layer for significantly enhanced performance of PLEDs

To enhance electroluminescence of polymer light-emitting diodes (PLEDs) using an environmentally stable aluminum cathode, we designed a novel water/alcohol-soluble electron injection material, FTC, composed of a fluorene core and triple azacrown ether terminals. FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/EML/EIL/Al] when used as the electron injection layer (EIL), especially in the presence of metal carbonates and metal acetates. The metal carbonate-doped devices showed the best performance due to their higher dissociation rate than metal acetates. In particular, the device using K2CO3 doped-FTC as the electron injection layer (EIL) exhibited significantly enhanced performance compared to the device without an EIL. For the device based on PF-Green-B as the emitting layer, the performance was significantly enhanced to 17:460 cd m -2, 21.58 cd A-1, and 12.42 lm W-1, respectively, from 1220 cd m-2, 0.72 cd A-1, and 0.27 lm W-1 for the non-FTC device. Using HY-PPV as the emitting layer, the device performance was also significantly enhanced to 10:990 cd m-2, 6.93 cd A-1, and 5.27 lm W-1, respectively, from 680 cd m-2, 0.07 cd A-1, and 0.03 lm W-1 for the non-EIL device. The results indicate that FTC with metal cations is an excellent electron injection candidate for the performance enhancement of PLEDs with a high work function Al cathode.

Solvent-free Claisen condensation of isophorone and verbenone with para-hydroxyethylaminobenzaldehydes

A solvent-free Claisen condensation between isophorone or verbenone on two para-hydroxyethylaminobenzaldehydes is described. The method provides the condensation products quickly and, in most cases, without chromatography. Copyright Taylor & Francis Group, LLC.

Multi-photon absorption organotin complex for bioimaging and promoting ROS generation

Compared to general fluorescent dyes, multi-photon fluorescent dyes exhibit deeper tissue penetration and lower auto-fluorescence in the bio-imaging field. Therefore, it is necessary to develop an efficient multiphoton imaging agent for deep tissue imaging. In this work, an organotin derivative (HSnBu3) has been designed and synthesized, which shows multiphoton absorption activity. In constrast to the ignorable three-photon activity of the ligand, the complex (HSnBu3) exhibits three-photon activity under NIR excitation (1500 nm). Results of chemical and biological tests confirmed that HSnBu3 was more easily activated by oxygen resulting in a higher level of 1O2, which could induce a decrease in mitochondrial membrane potential in HepG2 cells. It suggests that HSnBu3 has potential in photodynamic therapy.

A BODIPY-based fluorescent sensor for the detection of Pt2+ and Pt drugs

A BODIPY-based fluorescent sensor PS with an NO4S2 podand ligand was studied for the selective detection of Pt2+ over 21 cations as well as selected platinum drugs in aqueous medium. The platinum sensor PS shows 28-fold, 22-fold and 14-fold fluorescence turn-on enhancements to Pt2+, cisplatin and nedaplatin, and was thereby employed to detect platinum drugs in A-549 human lung cancer cells.

Precious metal-free molecular machines for solar thermal energy storage

Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes (4b and 4d) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of trans-cis photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs. The chemical structures of all dyes in the series were characterized by NMR, UV-vis, IR spectroscopy and elemental analysis. The steady-state photophysical properties of the dyes were elucidated. The stability constants of metal complexes were determined and are in good agreement with the literature data for reference dyes. The temporal evolution of trans-to-cis isomerization was observed in a real-time regime. The dyes demonstrated a low intrinsic fluorescence of their Ba2+ complexes and high yield of E/Z photoisomerization with lifetimes of the higher energy form longer than 500 seconds. Density functional theory (DFT) calculations at the B3LYP/6-31+G(d,p) level were performed in order to predict the enthalpies (H) of the cis and trans isomers and the storage energies (ΔH) for the systems studied.

A fluorene-based material containing triple azacrown ether groups: Synthesis, characterization and application in chemosensors and electroluminescent devices

We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) not only for application in aqueous solution as a chemosensor towards Fe3+ but also to enhance the electroluminescence of PLEDs using an environmentally stable aluminum cathode. The photo-physical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy. The FTC exhibited specific selectivity and high sensitivity toward Fe3+, with the Stern-Volmer coefficients (Ksv) being 1.59 × 105 M-1 in a solvent mixture of tetrahydrofuran and water (THF-H2O = 9/1, v/v). The FTC maintained high selectivity toward Fe3+ in the presence of ten interfering metal cations. The HOMO and LUMO levels were estimated to be -5.88 eV and -2.88 eV, respectively. The FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/MEH-PPV/EIL/Al] when used as an electron injection layer (EIL), especially in the presence of metal carbonates. Particularly, the device using K2CO3 doped FTC as the electron-injection layer (EIL) exhibited significantly enhanced performance compared to the one without EIL. The performance was significantly enhanced to 11630 cd m-2 and 1.47 cd A-1, respectively, from 230 cd m-2 and 0.03 cd A -1 of the non-FTC device. Current results indicate that multifunctional fluorene-based material FTC is a potential candidate for selective detection of Fe3+ and as an effective electron injection layer to enhance the performance of MEH-PPV.

Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization and application to enhancement of electroluminescence

Using an environmentally stable metal as the cathode in a polymer light-emitting diode (PLED) is an essential requirement for its practical application. We present the preparation of a water/alcohol soluble copoly(p-phenylene) (P1) containing pendant azacrown ether and ethylene glycol ether groups as a highly efficient electron injection layer (EIL) for PLEDs, allowing the use of environmentally stable aluminum as the cathode. Multilayer PLEDs [ITO/PEDOT:PSS/PF-Green-B/EIL/Al] using P1 as EIL exhibit significantly enhanced device performance, particularly in the presence of K 2CO3 or Cs2CO3. The maximum luminous power efficiency and maximum luminance of the device with Cs2CO 3-doped P1 as EIL were enhanced to 9.16 lm W-1 and 17050 cd m-2, respectively, compared with those without EIL (0.16 lm W -1, 890 cd m-2). The turn-on voltage was also significantly reduced from 5.7 V to 3.7 V simultaneously. The performance enhancement has been attributed to improved electron injection which has been confirmed by the rise in open-circuit voltage (Voc) obtained from photovoltaic measurements. The incorporation of such an electron injection layer significantly enhances device performance for PLEDs with an environmentally stable metal as the cathode.

Copoly(p-phenylene) containing azacrown ether: Synthesis, optical properties, and application for chemical sensor

Copoly(p-phenylene) (P1) containing pendent azacrown ether and ethylene glycol ether was prepared by the Suzuki coupling reaction and applied for chemical sensor. Poly(p-phenylene) derivative P0 without the azacrown ether groups were also synthesized for comparative study. The photophysical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy to elucidate the influence of the azacrown ether groups. The P1 exhibited specific selectivity and high sensitivity toward Zn2+, with the Stern-Volmer coefficient (Ksv) being 3.66 × 106 M-1 at low concentration in mixture solvent of tetrahydrofuran and water (THF/H2O = 9/1, v/v). The P1 maintained high selectivity toward Zn2+ in the presence of fifteen interfering metal cations. This results indicate that copoly(p-phenylene) (P1) is a promising functional material for chemical sensors. Copyright

Aminostilbazolium derivatives substituted by hydroxyethyl groups for second-order nonlinear optics

As DAST (1-methyl-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium p-toluenesulfonate) derivatives for improved crystal stability and inhibition of crystal water inclusion, 1-(2-hydroxyethyl)-4-(2-{4-[bis(2-hydroxyethyl)amino] phenyl}ethenyl)pyridinium salts 2 (2a-2l) and 1-(2-hydroxyethyl)-4-{2-[4- (diethylamino)phenyl]ethenyl}pyridinium salts 3 (3a-3l) were synthesized and their properties were investigated. Salts 3 were found to have no crystal water, and the cation with one hydroxyethyl group was effective to eliminate water inclusion in the crystals. Although the melting points of 2 were lower than those of the corresponding 3, decomposition temperatures of these chromophores were above 250°C indicating their good thermal stability. Crystals of m-nitrobenzenesulfonate salt 3f was obtained without crystal water and showed SHG activity. Copyright Taylor & Francis Group, LLC.

Synthesis, spectroscopy and photochemistry of novel branched fluorescent nitro-stilbene derivatives with benzopheonone groups

In this article, we presented novel nitro-stilbene derivatives with one or two benzophenone groups as photoinitiators via multi-steps synthesis. The ultraviolet/visible spectroscopy and the emission spectroscopy of the compounds were determined in various solvents. The results showed that the ultraviolet/visible absorption spectroscopy of the derivatives with benzophenone moiety displayed overlap effects of nitro-stilbene and benzophenone parts. In non-polar solvents, the derivatives exhibited strong emission, while they displayed weak emission in modest and strong polar solvents. Dyes-linked benzopheonone groups displayed stronger fluorescence emission than simple chromophore parent molecules. Visible-light photoinitiating effects of the derivatives were investigated extensively. Methyl methacrylate could be photoinitiated efficiently by the derivatives with benzophenone moieties at very low concentration, even at 1×10-5 mol/ L. While the photopolymerization efficiency of styrene initiated by the derivatives was lower than that of methyl methacrylate. Our results showed that the dye-linked photoinitators had more efficient photoinitiating than the simple mixture of dye and photoinitator. Furthermore, the derivative with two benzophenone groups displayed more excellent phototiniatiating effects than the derivative with one benzophenone group. Thermodynamics driving for the occurrence of visible-light photoinduced intramolecular electron transfer from chromophore part to benzophenone part was evaluated. Benzopinacol moiety produced in photoreaction was confirmed by nuclear magnetic resonant spectroscopy. Thermal stability of the derivatives was analyzed. Springer Science+Business Media, LLC 2010.