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
• Article Data: 13

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

General Description

4-[N,N-Bis(2-hydroxyethyl)amino]benzaldehyde, also known as BHAM, is a chemical compound with the molecular formula C15H21N3O3. It is an aldehyde derivative of benzaldehyde that contains two hydroxyethylamine groups. BHAM is often used as a cross-linking agent in the production of acrylic-based polymers and can also be employed as a corrosion inhibitor in metalworking fluids. Additionally, it has been studied for its potential anti-tumor and anti-inflammatory properties. BHAM is a versatile compound with various industrial and biomedical applications due to its unique chemical structure and properties.

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

• 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 
• 41313-77-3 4-(bis(2-acetoxyethyl)amino)benzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 83772-59-2 4-<4-benzylidene>-4'-N,N-dimethylaminoaniline 

Downstream Products

• 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 
• 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 
• 716378-74-4 C₂₂H₂₂N₄O₃ 
• 1314797-75-5 C₂₀H₂₉NO₈ 
• 1262030-00-1 4-N,N-di[2-(p-benzoylphenylmethoxy)ethyl]amino-4'-nitrostilbene 
• 959738-54-6 C₃₂H₄₅N₅O₃Si₂ 
• 1180565-17-6 C₅₅H₈₃N₅O₅Si₂ 
• 1383604-15-6 C₄₃H₅₅N₅O₅ 
• 66749-96-0 4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzaldehyde 
• 1496526-47-6 C₂₁H₂₇N₂O₂⁽¹⁺⁾*Br^(1-) 

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.

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.

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.

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.