80547-69-9

Basic information

• Product Name: 3-hydroxy-4-methoxy-5-nitrobenzaldehyde
• Synonyms: 3-hydroxy-4-methoxy-5-nitrobenzaldehyde
• CAS NO: 80547-69-9
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14
• Mol File: 80547-69-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 373°C at 760 mmHg
• Flash Point: 179.4°C
• Appearance: /
• Density: 1.456g/cm³
• Vapor Pressure: 4.32E-06mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: 3-hydroxy-4-methoxy-5-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-4-methoxy-5-nitrobenzaldehyde(80547-69-9)
• EPA Substance Registry System: 3-hydroxy-4-methoxy-5-nitrobenzaldehyde(80547-69-9)

Safety Data

• Hazardous Substances Data: 80547-69-9(Hazardous Substances Data)

Usage

General Description

3-Hydroxy-4-methoxy-5-nitrobenzaldehyde is a chemical compound that belongs to the class of aromatic aldehydes. It is a yellow crystalline powder with the molecular formula C8H7NO5 and a molecular weight of 197.15 g/mol. 3-hydroxy-4-methoxy-5-nitrobenzaldehyde is commonly used as an intermediate in the synthesis of various pharmaceuticals, dyes, and organic compounds. It is also known for its antibacterial and antifungal properties. 3-Hydroxy-4-methoxy-5-nitrobenzaldehyde has the potential for various applications in the fields of medicine, agriculture, and industrial chemistry due to its versatile chemical properties.

InChI:InChI=1/C8H7NO5/c1-14-8-6(9(12)13)2-5(4-10)3-7(8)11/h2-4,11H,1H3

Upstream product

• 621-59-0 isovanillin 
• 881-57-2 isovanillin acetate 
• 80547-72-4 acetic acid 5-formyl-2-methoxy-3-nitrophenyl ester 

Downstream Products

• 100966-07-2 4-methoxy-5,3'-dinitro-3,4'-oxy-di-benzaldehyde 
• 343867-62-9 3-Amino-5-hydroxy-4-methoxy-benzaldehyde 
• 886442-65-5 3-tert-butyldimethylsilyloxy-4-methoxy-5-nitrobenzaldehyde 
• 519060-27-6 2-Methoxy-3-nitro-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol 
• 886442-73-5 (Z)-2-(3'-tert-butyldimethylsilyloxy-4'-methoxy-5'-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethene 
• 54246-06-9 3-chloro-5-hydroxy-4-methoxybenzaldehyde 
• 80547-63-3 3-chloro-5-hydroxy-4-methoxybenzoic acid 
• 1314797-69-7 C₁₇H₂₁NO₁₀ 
• 116313-85-0 3,4-dihydroxy-5-nitrobenzaldehyde 
• 1081273-75-7 phenethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate 
• 130929-57-6 entacapone 
• 1047659-01-7 entacapone; piperidine salt 
• 116314-52-4 ethyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate 

Relevant articles and documents

Synthesis and Biochemical Evaluation of 3-Phenoxy-1,4-diarylazetidin-2-ones as Tubulin-Targeting Antitumor Agents

Structure-activity relationships for a series of 3-phenoxy-1,4-diarylazetidin-2-ones were investigated, leading to the discovery of a number of potent antiproliferative compounds, including trans-4-(3-hydroxy-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (78b) and trans-4-(3-amino-4-methoxyphenyl)-3-phenoxy-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (90b). X-ray crystallography studies indicate the potential importance of the torsional angle between the 1-phenyl A ring and 4-phenyl B ring for potent antiproliferative activity and that a trans configuration between the 3-phenoxy and 4-phenyl rings is generally optimal. These compounds displayed IC50 values of 38 and 19 nM, respectively, in MCF-7 breast cancer cells, inhibited the polymerization of isolated tubulin in vitro, disrupted the microtubular structure in MCF-7 cells as visualized by confocal microscopy, and caused G2/M arrest and apoptosis. Compound 90b possessed a mean GI50 value of 22 nM in the NCI60 cell line screen, displayed minimal cytotoxicity, and was shown to interact at the colchicine-binding site on β-tubulin. Phosphate and amino acid prodrugs of both 78b and 90b were synthesized, of which the alanine amide 102b retained potency and is a promising candidate for further clinical development.

Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel

The reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six- center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation.