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

• 836-43-1 4-benzyloxybenzyl alcohol 
• 76193-67-4 4-benzyloxybenzaldehyde oxime 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-51-6 benzyl alcohol 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 6793-92-6 p-benzyloxyphenylbromide 
• 201230-82-2 carbon monoxide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 66605-58-1 O-benzyl N-Boc-L-tyrosinol 
• 27513-44-6 N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester 
• 623-05-2 (4-hydroxyphenyl)methanol 

Downstream Products

• 73839-66-4 α-(4-Benzyloxybenzyliden)-butyrolacton 
• 61439-56-3 p-[p-(Benzyloxy)benzylamino]benzoic Acid 
• 61439-55-2 ethyl 4-({[4-(benzyloxy)phenyl]methyl}amino)benzoate 
• 65183-31-5 2-(4-benzyloxy-benzylidene)-6-nitro-benzo[4,5]imidazo[2,1-b]thiazol-3-one 
• 95332-25-5 3-(4-Benzyloxy-phenyl)-oxirane-2-carboxylic acid ethyl ester 
• 328396-03-8 (-)-ethyl 3-(4-benzyloxyphenyl)-3-hydroxypropionate 
• 75676-91-4 1-(4-benzyloxyphenyl)but-1-en-3-one 
• 78932-95-3 [1-(4-Benzyloxy-phenyl)-meth-(E)-ylidene]-[4-(4-phenyl-piperazin-1-yl)-phenyl]-amine 
• 78771-47-8 N-Benzhydryl-2-(4-benzyloxy-phenyl)-2-(2-oxo-azetidin-1-yl)-acetamide 
• 174422-18-5 2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid 
• 1486-51-7 p-(benzyloxy)benzoic acid 

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

The condensation of 4-benzyloxybenzaldehyde with S-methyldithiocarbazate (SMDTC) yielded the Schiff base methyl-3-[(4-benzyloxyphenyl)methylene] dithiocarbazate (HL) that, upon reaction with different metal ions, afforded bis-chelated complexes, ML2

Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process

Here we report a mild and general method for the trifluoromethylthiolation of aldehydes using N-trifluoromethylthiosaccharin as the CF3S radical source and sodium decatungstate (NaDT) as the photocatalyst. This reaction proceeds via hydrogen at

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.

Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water

A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.