4397-53-9

Basic information

• Product Name: 4-Benzyloxybenzaldehyde
• Synonyms: AKOS AU36-M28;AKOS BBS-00003143;4-BENZYLOXYBENZALDEHYDE;LABOTEST-BB LT00233210;ASISCHEM R39515;TIMTEC-BB SBB000526;P-(BENZYLOXY)BENZALDEHYDE;P-BENZYLOXY BENZALDEYHDE
• CAS NO: 4397-53-9
• Molecular Formula: C14H12O2
• Molecular Weight: 212.24
• EINECS: 224-527-2
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Aldehydes;C10 to C21;Carbonyl Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4397-53-9.mol
• Article Data: 217

Chemical Properties

• Melting Point: 71-74 °C(lit.)
• Boiling Point: 197-199 °C (11 mmHg)
• Flash Point: 197-199°C/20mm
• Appearance: Creamish to yellow/Crystalline Powder
• Density: 1.1035 (rough estimate)
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Sparingly)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 1242385
• CAS DataBase Reference: 4-Benzyloxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Benzyloxybenzaldehyde(4397-53-9)
• EPA Substance Registry System: 4-Benzyloxybenzaldehyde(4397-53-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 9-23
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 4397-53-9(Hazardous Substances Data)

Usage

Chemical Properties

creamish to yellow crystalline powder

Uses

Different sources of media describe the Uses of 4397-53-9 differently. You can refer to the following data:
1. 4-Benzyloxybenzaldehyde is a position isomer of the adenylyl cyclase activator 2-Benzyloxybenzaldehyde. 4-Benzyloxybenzaldehyde also has much less potent anticancer activity against HL-60 cells that i ts isomeric counterpart.
2. 4-Benzyloxybenzaldehyde is used in the synthesis of (5-fluoro-(2R*,3S*)-2,3-bis(4-hydroxyphenyl)pentanenitrile),an estrogen receptor β-selective ligand. It is a position isomer of the adenylyl cyclase activator 2-benzyloxybenzaldehyde.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 192, 1989 DOI: 10.1021/jm00121a035

General Description

4-(Benzyloxy)benzaldehyde was used in the synthesis of (5-fluoro-(2R*,3S*)-2,3-bis(4-hydroxyphenyl)pentanenitrile),an estrogen receptor β-selective ligand.

InChI:InChI=1/C14H12O2/c15-10-12-6-8-14(9-7-12)16-11-13-4-2-1-3-5-13/h1-10H,11H2

Upstream product

• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-44-7 benzyl chloride 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 76193-67-4 4-benzyloxybenzaldehyde oxime 
• 74994-62-0 4-(benzyloxy)-3-iodobenzaldehyde 
• 140174-89-6 (2S)-2-N-Boc-amino-3-(4-benzyloxyphenyl)propyl acetate 
• 69455-12-5 4-benzyloxy-3-bromobenzaldehyde 
• 188038-47-3 3'-[4-(phenylmethoxy)phenyl][5,6]fullereno-C₆₀-I_h-[1,9-d]isoxazole 
• 205578-45-6 9-(4-Benzyloxy-benzyl)-9H-carbazole 
• 74317-66-1 p-benzyloxybenzaldehyde dimethyl acetal 
• 39236-04-9 2-(4-(benzyloxy)phenyl)-1,3-dithiane 
• 61439-59-6 2-(4-benzyloxyphenyl)ethanol 

Downstream Products

• 73839-66-4 α-(4-Benzyloxybenzyliden)-butyrolacton 
• 84002-48-2 (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 111391-35-6 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 
• 19158-99-7 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 2982-55-0 1-benzyloxy-4-(2-nitroethenyl)benzene 
• 2982-55-0 (E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene 
• 114160-09-7 3t-(4-benzyloxy-phenyl)-1-(1-hydroxy-[2]naphthyl)-propenone 
• 111391-33-4 4-benzyloxy-2'-hydroxy-6'-methoxy-trans-chalcone 
• 103050-95-9 3t-(4-benzyloxy-phenyl)-1-(4-bromo-1-hydroxy-[2]naphthyl)-propenone 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 76193-67-4 4-benzyloxybenzaldehyde oxime 
• 652539-35-0 7,4'-dibenzyloxy-2-styrylchromone 
• 111391-32-3 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 86711-45-7 (E)-3-(4-(benzyloxy)phenyl)-1-(p-tolyl)prop-2-en-1-one 

Relevant articles and documents

Coordination chemistry of [methyl-3-(4-benzyloxyphenyl)methylene] dithiocarbazate with divalent metal ions: Crystal structures of the N,S Schiff base and of its bis-chelated nickel(II) complex

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Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process

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Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Chemoselective and ligand-free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina-supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst

An economically efficient and operationally simple ligand-free protocol for the chemoselective oxidation of benzylic alcohols to carbonyl compounds has been developed using alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst along with potassium tert-butoxide in the presence of aerial oxygen as an eco-friendly oxidant. The aliphatic alcohols remained unaffected under the present condition. Excellent chemoselectivity has also been demonstrated through intermolecular and intramolecular competition experiments. This protocol accommodates a diverse range of substituents with the tolerance of various sensitive moieties during the reaction. The catalyst could be recovered by filtration and reused consecutively without any significant loss in the catalytic activity. Moreover, the heterogeneity of the catalyst has also been established by the “hot filtration method (Sheldon's test)”.