67565-48-4

Basic information

• Product Name: 4-(4-NITROBENZYLOXY)BENZALDEHYDE
• Synonyms: 4-(P-NITROBENZYLOXY)BENZALDEHYDE;4-(4-NITROBENZYLOXY)BENZALDEHYDE;ASISCHEM R22436;4-(4-Nitrobenzyloxy)benzaldehyde 98%;4-[(4-Formylphenoxy)methyl]nitrobenzene;4-[(4-Nitrobenzyl)oxy]benzaldehyde98%
• CAS NO: 67565-48-4
• Molecular Formula: C₁₄H₁₁NO₄
• Molecular Weight: 257.24
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 67565-48-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 133-134°C
• Boiling Point: 456.6 °C at 760 mmHg
• Flash Point: 211 °C
• Appearance: /
• Density: 1.301 g/cm³
• Vapor Pressure: 1.6E-08mmHg at 25°C
• Refractive Index: 1.634
• Sensitive: Air Sensitive
• BRN: 1884256
• CAS DataBase Reference: 4-(4-NITROBENZYLOXY)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-NITROBENZYLOXY)BENZALDEHYDE(67565-48-4)
• EPA Substance Registry System: 4-(4-NITROBENZYLOXY)BENZALDEHYDE(67565-48-4)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 67565-48-4(Hazardous Substances Data)

Usage

General Description

4-(4-NITROBENZYLOXY)BENZALDEHYDE is a chemical compound with the molecular formula C14H11NO4. It is a yellow crystalline solid that is commonly used in the production of pharmaceuticals and organic synthesis. It is also known as 4-(4-nitrophenylmethoxy)benzaldehyde and is used as a reagent in various chemical reactions. 4-(4-NITROBENZYLOXY)BENZALDEHYDE is known for its strong aromatic properties and is often used as a building block in the production of more complex organic compounds. It is important to handle this compound with care, as it is a potential irritant and may cause skin and eye irritation upon contact.

InChI:InChI=1/C14H11NO4/c16-9-11-3-7-14(8-4-11)19-10-12-1-5-13(6-2-12)15(17)18/h1-9H,10H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 100-14-1 4-nitrobenzyl chloride 

Downstream Products

• 1392419-47-4 C₂₄H₁₅F₃N₂O₅ 
• 1350613-29-4 C₂₄H₁₈N₄O₄ 
• 1350613-33-0 C₂₄H₂₀N₄O₂ 
• 1350613-36-3 C₂₆H₂₂N₄O₃ 

Relevant articles and documents

ON THE FIRST EXAMPLE OF AN INVERTED SEQUENCE SA N SC IN A PURE POLAR COMPOUND.

Six homologues of the new series 4- left bracket 4 prime -nitrobenzyloxy right bracket benzylidene-4 double prime -alkoxyaniline are presented. The reentrant sequence I N S//A N//r//e S//C was found for the first time in the pure compound: 4- left bracket 4 prime -nitrobenzyloxy right bracket benzylidene-4 double prime -undecyloxaniline, while the dodecyloxy derivative presents the inverted sequence IS//A N S//C S//1.

NTR-1 response type fluorescent probe based on benzoindole as well as preparation method and application thereof

The invention discloses an NTR-1 response type fluorescent probe based on benzoindole as well as a preparation method and application of the NTR-1 response type fluorescent probe. The structure of the NTR-1 response type fluorescent probe is as defined in the specification. The method comprises the following steps: subjecting p-hydroxybenzaldehyde to reacting with p-nitrobenzyl bromide to synthesize a stable intermediate NFP-1-M connected through ether bonds, and condensing 1-ethyl-2-methylbenzo[cd]indole-1-chloride with the intermediate NFP-1-M to generate the probe NFP-1. The probe can be used for measuring the hypoxia degree of a cell, and is beneficial to early diagnosis of tumors and the like.

Design, synthesis and biological evaluation of tetrahydroquinoline-based reversible LSD1 inhibitors

The targeted regulation of LSD1, which is highly expressed in a variety of tumor cells, is a promising cancer therapy strategy. Several LSD1 inhibitors are currently under clinical evaluation, and most of these inhibitors are irreversible. Here, we report the design, synthesis and biochemical evaluation of novel tetrahydroquinoline-based reversible LSD1 inhibitors. Compounds 18s and 18x, which are selective to LSD1 over MAO-A/B, exhibit excellent LSD1 inhibition at the molecular levels with IC50 = 55 nM and 540 nM, respectively. The classic Lineweaver–Burk plots revealed that compound 18s could reversibly bind the LSD1 enzyme in a noncompetitive manner. Molecular docking was used to reveal the potential binding-mode of the compounds and interpret the structure-activity relationships. Furthermore, compounds 18s and 18x significantly inhibited proliferation (IC50 = 1.13 μM and 1.15 μM, respectively) and induced apoptosis in MGC-803 cells with high expression of LSD1. Compound 18x showed acceptable liver microsomal stability. Meanwhile, 18x did not appear to inhibit CYPs at 10 μM in vitro. Remarkably, the oral administration of compound 18x can inhibit the growth of MGC-803 xenograft tumors without significant side effects. Our findings suggest that tetrahydroquinoline-based LSD1 inhibitors deserve further investigation for the treatment of LSD1 overexpressing cancer.