Welcome to LookChem.com Sign In|Join Free
  • or

Encyclopedia

2-Hydroxy-3-methoxybenzaldehyde

Base Information Edit
  • Chemical Name:2-Hydroxy-3-methoxybenzaldehyde
  • CAS No.:148-53-8
  • Molecular Formula:C8H8O3
  • Molecular Weight:152.15
  • Hs Code.:29124900
  • European Community (EC) Number:205-715-3
  • NSC Number:2150
  • UNII:008LR748FI
  • DSSTox Substance ID:DTXSID5022011
  • Nikkaji Number:J45.622E
  • Wikipedia:Ortho-Vanillin
  • Wikidata:Q309747
  • Metabolomics Workbench ID:123411
  • ChEMBL ID:CHEMBL13859
  • Mol file:148-53-8.mol
2-Hydroxy-3-methoxybenzaldehyde

Synonyms:2-hydroxy-3-methoxybenzaldehyde;2-vanillin;o-vanilin;o-vanillin

Suppliers and Price of 2-Hydroxy-3-methoxybenzaldehyde
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • 2-Vanillin
  • 250g
  • $ 90.00
  • TCI Chemical
  • o-Vanillin >99.0%(GC)
  • 500g
  • $ 129.00
  • TCI Chemical
  • o-Vanillin >99.0%(GC)
  • 100g
  • $ 51.00
  • TCI Chemical
  • o-Vanillin >99.0%(GC)
  • 25g
  • $ 23.00
  • SynQuest Laboratories
  • 2-Hydroxy-3-methoxybenzaldehyde
  • 10 g
  • $ 72.00
  • SynQuest Laboratories
  • 2-Hydroxy-3-methoxybenzaldehyde
  • 500 g
  • $ 392.00
  • SynQuest Laboratories
  • 2-Hydroxy-3-methoxybenzaldehyde
  • 100 g
  • $ 120.00
  • Sigma-Aldrich
  • o-Vanillin 99%
  • 500g
  • $ 162.00
  • Sigma-Aldrich
  • o-Vanillin 99%
  • 100g
  • $ 83.70
  • Sigma-Aldrich
  • o-Vanillin 99%
  • 10g
  • $ 24.30
Total 142 raw suppliers
Chemical Property of 2-Hydroxy-3-methoxybenzaldehyde Edit
Chemical Property:
  • Appearance/Colour:Pale yellow to brown low melting solid 
  • Vapor Pressure:0.00556mmHg at 25°C 
  • Melting Point:40-42 °C(lit.) 
  • Refractive Index:1.587 
  • Boiling Point:265.5 °C at 760 mmHg 
  • PKA:pK1:7.912 (25°C) 
  • Flash Point:94 °C 
  • PSA:46.53000 
  • Density:1.231 g/cm3 
  • LogP:1.21330 
  • Storage Temp.:Store below +30°C. 
  • Sensitive.:Air Sensitive 
  • Solubility.:Chloroform (Sparingly), Methanol (Slightly) 
  • Water Solubility.:slightly soluble 
  • XLogP3:1.4
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:2
  • Exact Mass:152.047344113
  • Heavy Atom Count:11
  • Complexity:135
Purity/Quality:

99% *data from raw suppliers

2-Vanillin *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn,IrritantXi 
  • Hazard Codes:Xn,Xi 
  • Statements: 22-36/37/38 
  • Safety Statements: 23-36-24/25-36/37/39-27-26 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Biological Agents -> Plant Oils and Extracts
  • Canonical SMILES:COC1=CC=CC(=C1O)C=O
  • General Description 3-Methoxysalicylaldehyde (also known as o-vanillin or 2-hydroxy-3-methoxybenzaldehyde) is a versatile aromatic aldehyde used as a key intermediate in the synthesis of Schiff base ligands for metal complexes, such as copper(II) and zinc(II) compounds with potential analgesic, antipyretic, and anti-inflammatory properties. It also serves as a starting material in the multistep synthesis of bioactive alkaloids like (+)-pancratistatin, an antitumor agent, and contributes to the development of cytotoxic tin(IV) complexes for cancer therapy. Its structural features, including the hydroxy and methoxy substituents, facilitate coordination with metal ions and participation in condensation reactions, making it valuable in medicinal and organometallic chemistry.
Technology Process of 2-Hydroxy-3-methoxybenzaldehyde

There total 41 articles about 2-Hydroxy-3-methoxybenzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
In neat (no solvent); at 20 ℃; for 0.0333333h; Microwave irradiation;
DOI:10.33224/rrch.2020.65.3.08
Guidance literature:
With lithium chloride; In N,N-dimethyl-formamide; for 22h; Heating;
DOI:10.1055/s-1989-27225
Guidance literature:
N,N-dimethyl-formamide; 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate; With tetrabutyl ammonium fluoride; at 20 ℃; for 3h; Inert atmosphere;
With water;
DOI:10.1016/j.tet.2011.10.072
Refernces Edit

In vivo assessment of newly synthesized achiral copper(ii) and zinc(ii) complexes of a benzimidazole derived scaffold as a potential analgesic, antipyretic and anti-inflammatory

10.1039/c5ra25071d

The research presented in the "RSC Advances" manuscript focuses on the synthesis and in vivo assessment of newly synthesized achiral copper(II) and zinc(II) complexes derived from benzimidazole. The study aimed to evaluate their potential as analgesic, antipyretic, and anti-inflammatory agents. The reactants used in the synthesis include 2-aminobenzimidazole, o-vanillin, Cu(NO3)2·3H2O, and Zn(NO3)2·6H2O. The Schiff base ligand was synthesized by refluxing 2-aminobenzimidazole and o-vanillin in absolute ethanol, followed by recrystallization. The copper(II) and zinc(II) complexes were then synthesized by reacting the Schiff base with the respective metal nitrate salts in methanol. Characterization of the ligand and complexes was performed using various analytical and spectroscopic techniques, including infrared (IR), proton (1H) and carbon-13 (13C) nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), high-resolution mass spectrometry (HRMS), and ultra-performance liquid chromatography (UPLC). The in vivo biological activities were assessed using mice and rats models for antipyretic (yeast-induced hyperpyrexia), analgesic (acetic acid-induced writhing), and anti-inflammatory (carrageenan-induced paw edema) effects. The experiments were conducted following ethical guidelines, and the results were statistically analyzed using one-way ANOVA and Dunnett's post-hoc test.

Application of the β-azidonation reaction to the synthesis of the antitumor alkaloid (+)-pancratistatin

10.1016/S0040-4020(98)00975-2

The research focuses on the synthesis of the antitumor alkaloid (+)-pancratistatin, a compound isolated from the Hawaiian plant Pancratium littorale, which shows significant potential as a clinically useful antitumor agent. The study aims to develop a reliable and efficient synthetic route to (+)-pancratistatin due to the limited natural supply of the alkaloid. The synthesis process involves a series of chemical reactions, including dehydration, hydrogenation, hydrolysis, and the use of the [3-azidonation reaction on triisopropylsilyl (TIPS) enol ethers, leading to the formation of the key intermediates and ultimately (+)-pancratistatin. Key chemicals used in the synthesis include o-vanillin, n-BuLi/TI-IF, POCI3/pyridine/DBU, LiAlH4, MCPBA, KOBut/HMPA, and various other reagents and solvents. The successful synthesis was achieved in 22 steps from commercially available o-vanillin with an overall yield of 1.2%, marking a significant advancement in the field of alkaloid chemistry and potentially providing a more accessible source of this important antitumor agent.

Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

10.1016/j.molstruc.2019.127635

The research aimed to synthesize and evaluate a series of octahedral homoleptic tin(IV) compounds derived from tridentate ONS dithiocarbazate Schiff bases for their potential cytotoxic effects against various cancer cell lines. The key chemicals used in the synthesis included tin(II) chloride, dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde and 2,3-dihydroxybenzaldehyde, and various substituted benzyl groups. The compounds were characterized using elemental analysis, FT-IR, multinuclear NMR (1H, 13C, and 119Sn), and X-ray crystallography. Density functional theory (DFT) calculations were employed to validate the experimental findings. The study concluded that five of the synthesized tin(IV) compounds exhibited higher cytotoxicity against HT29, MCF7, and MIA cancer cell lines compared to the reference drug cisplatin, suggesting their potential as chemotherapeutic agents. The research highlights the significance of ligand modification in enhancing the bioactivity of metal-based compounds for cancer therapy.

Post RFQ for Price