67-36-7

Basic information

• Product Name: 4-Phenoxybenzaldehyde
• Synonyms: DIPHENYL ETHER 4-CARBOXALDEHYDE;4-FORMYLDIPHENYL ETHER;4-PHENOXYBENZALDEHYDE;4-phenoxy-benzaldehyd;Benzaldehyde, 4-phenoxy-;Benzaldehyde, p-phenoxy-;p-phenoxy-benzaldehyd;p-Phenoxybenzaldehyde
• CAS NO: 67-36-7
• Molecular Formula: C₁₃H₁₀O₂
• Molecular Weight: 198.22
• EINECS: 200-650-7
• Product Categories: Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C10 to C21;Carbonyl Compounds;Building Blocks;C13-C60
• Mol File: 67-36-7.mol
• Article Data: 92

Chemical Properties

• Melting Point: 24-25 °C(lit.)
• Boiling Point: 185 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid After Melting
• Density: 1.132 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000325mmHg at 25°C
• Refractive Index: n20/D 1.611(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, Methanol
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 1947841
• CAS DataBase Reference: 4-Phenoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenoxybenzaldehyde(67-36-7)
• EPA Substance Registry System: 4-Phenoxybenzaldehyde(67-36-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• RTECS: CU7560000
• F: 10
• Hazardous Substances Data: 67-36-7(Hazardous Substances Data)

Usage

Description

4-Phenoxybenzaldehyde is an organic compound with the molecular formula C13H10O2. It is a clear, colorless to yellow liquid at room temperature and serves as a crucial precursor in the synthesis of various chemical products, particularly in the agrochemical industry.

Uses

Used in Agrochemical Industry:
4-Phenoxybenzaldehyde is used as a precursor for the synthesis of para-Cypermethrin (C989400), a widely used pyrethroid insecticide. Its role in the production of this insecticide is essential for controlling a broad spectrum of pests in agriculture, thereby contributing to increased crop yields and protection against damage caused by insects.
Used in Environmental Research:
4-Phenoxybenzaldehyde has been identified as a compound that can cause acute toxicity to the protozoan ciliate Tetrahymena pyriformis. This information is valuable in environmental research and risk assessment, as it helps to understand the potential ecological impact of this compound and its derivatives. The toxicity prediction is based on quantitative structure-activity relationship (QSAR) models, which provide insights into the relationship between the chemical structure of a compound and its biological effects.

InChI:InChI=1/C13H10O2/c14-10-11-6-8-13(9-7-11)15-12-4-2-1-3-5-12/h1-10H

Upstream product

• 101-84-8 diphenylether 
• 74-90-8 hydrogen cyanide 
• 36881-42-2 1-(bromomethyl)-4-phenoxybenzene 
• 100-97-0 hexamethylenetetramine 
• 1623-95-6 4-phenoxybenzoyl chloride 
• 4039-92-3 4-phenoxybenzyl chloride 
• 1706-12-3 4-phenoxytoluene 
• 459-57-4 4-fluorobenzaldehyde 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 555-16-8 4-nitrobenzaldehdye 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 2974-94-9 4-phenoxyiodobenzene 

Downstream Products

• 95223-60-2 (Z)-4-(4-phenoxybenzylidene)-2-phenyloxazol-5(4H)-one 
• 62248-88-8 (E)-1-(2-nitrovinyl)-4-phenoxybenzene 
• 2215-78-3 (4-phenoxyphenyl)methanol 
• 2215-77-2 4-Phenoxybenzoic acid 
• 50961-54-1 4-(4-nitrophenoxy)benzaldehyde 
• 172932-06-8 4-(2-nitrophenoxy)benzaldehyde 
• 143128-45-4 4-(4-iodophenoxy)benzaldehyde 
• 860724-83-0 4-(2,4-dinitro-phenoxy)-3-nitro-benzaldehyde 
• 2215-83-0 p-phenoxycinnamic acid 
• 2215-83-0 4-phenoxycinnamic acid 
• 41616-59-5 (4-phenoxy-benzyliden)-aniline 
• 3506-98-7 4,4'-(4-phenoxy-phenylmethanediyl)-bis-morpholine 
• 3507-02-6 4-<(N-Methyl-morpholinio)-acetylhydrazonomethyl>-diphenylether iodid 
• 90672-15-4 (3-Methyl-isothiazol-5-yl)-(4-phenoxy-phenyl)-methanol 

Relevant articles and documents

Polymer supported reagents: Oxidative selection between benzylic alcohols

Dowex 1-X8, as a quaternary ammonium resin, on which CI- ? Cl- is replaced by dichromate and bisulfate ions (DDB), can be used as a stable and efficient oxidizing reagent for oxidative selection between benzylic alcohols according to their structures.

Synergistic effect of copper nanocrystals-nanoparticles incorporated in a porous organic polymer for the Ullmann C-O coupling r–eaction

A quinoxaline-based porous organic polymer (Q-POP) as a mesoporous organic copolymer was developed as a new platform for the immobilization of CuNPs and copper nanocrystals. The prepared materials were characterized by FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and single-crystal X-ray crystallography. The obtained catalyst presented extraordinary catalytic activity towards Ullmann C–O coupling reactions with high surface area, hierarchical porosity, and excellent thermal and chemical stability. Due to its high porosity, and synergistic effect of copper nanocrystals incorporated in the polymer composite, the as-synthesized catalyst was successfully utilized for the Ullmann C–O coupling reaction of phenols and different aryl halides to prepare various diaryl ether derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C–O coupling reaction with phenols to produce diaryl ethers in good to excellent yields (70–97 %), and it was found that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss.

Synthesis and biological evaluation of 4-phenoxy-phenyl isoxazoles as novel acetyl-CoA carboxylase inhibitors

Acetyl-CoA carboxylase (ACC) is a crucial enzyme in fatty acid metabolism, which plays a major role in the occurrence and development of certain tumours. Herein, one potential ACC inhibitor (6a) was identified through high-throughput virtual screening (HTVS), and a series of 4-phenoxy-phenyl isoxazoles were synthesised for structure-activity relationship (SAR) studies. Among these compounds, 6g exhibited the most potent ACC inhibitory activity (IC50=99.8 nM), which was comparable to that of CP-640186. Moreover, the antiproliferation assay revealed that compound 6l exhibited the strongest cytotoxicity, with IC50 values of 0.22 μM (A549), 0.26 μM (HepG2), and 0.21 μM (MDA-MB-231), respectively. The preliminary mechanistic studies on 6g and 6l suggested that the compounds decreased the malonyl-CoA levels, arrested the cell cycle at the G0/G1 phase, and induced apoptosis in MDA-MB-231 cells. Overall, these results indicated that the 4-phenoxy-phenyl isoxazoles are potential for further study in cancer therapeutics as ACC inhibitors.