2,3-Dihydroxybenzaldehyde

Base Information

• Chemical Name: 2,3-Dihydroxybenzaldehyde
• CAS No.: 24677-78-9
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 29124900
• European Community (EC) Number: 246-398-1
• NSC Number: 146456
• UNII: GP9HDE43LE
• DSSTox Substance ID: DTXSID90179411
• Nikkaji Number: J88.291G
• Wikidata: Q27104753
• Metabolomics Workbench ID: 52538
• ChEMBL ID: CHEMBL491995
• Mol file: 24677-78-9.mol

Synonyms:2,3-dihydroxybenzaldehyde;o-pyrocatechualdehyde

Chemical Property of 2,3-Dihydroxybenzaldehyde

Chemical Property:

• Appearance/Colour: light yellow to beige-greenish cryst. powder
• Vapor Pressure: 0.0252mmHg at 25°C
• Melting Point: 104-108 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 240 °C at 760 mmHg
• PKA: 8.01±0.10(Predicted)
• Flash Point: 113.2 °C
• PSA: 57.53000
• Density: 1.409 g/cm³
• LogP: 0.91030
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 95% ethanol: soluble50mg/mL, clear, colorless to greenish-yellow
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

2,3-Dihydroxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)O)C=O
• Uses: 2,3-disubstituted benzaldehyde. 2,3-Dihydroxybenzaldehyde was used in the synthesis of copper(II) complexes of Schiff bases. It was also used in the synthesis of 2-ethoxy-3-hydroxy-4-nitrobenzoic acid.

Technology Process of 2,3-Dihydroxybenzaldehyde

There total 23 articles about 2,3-Dihydroxybenzaldehyde 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:

Reference yield: 86.0%

3-ethoxysalicylaldehyde (492-88-6) → 2,3-dihydroxybenzaldehyde (24677-78-9)

Guidance literature:

With boron tribromide; In chloroform; 1. 0 deg C, 2.5 h; 2. room temperature, overnight;

Reference yield: 85.0%

2,3-dimethyoxybenzaldehyde (86-51-1) → 2,3-dihydroxybenzaldehyde (24677-78-9)

Guidance literature:

With boron tribromide; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1002/hlca.19830660415

Reference yield: 80.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 2,3-dihydroxybenzaldehyde (24677-78-9)

Guidance literature:

With magnesia; In neat (no solvent); for 0.3h; regioselective reaction; Microwave irradiation;

DOI:10.1039/c7nj04794k

upstream raw materials:

salicylaldehyde

3-methoxy-2-hydroxybenzaldehyde

3-ethoxysalicylaldehyde

chloroform

Downstream raw materials:

3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)methoxy-salicylaldehyde

C₅₇H₅₀O₁₅

C₂₅H₂₂O₇

Refernces

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.

Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: Reversal of enantioselectivity and rate acceleration on addition of AlCl₃

10.3906/kim-1005-607

The research investigates the asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives using Co(III) salen catalysts. The study found that the ring-opening occurred at the phenolic groups most distant from the aldehydic group. Notably, switching catalysts led to a reversal in enantioselectivity. The addition of AlCl3 to the reaction mixture significantly accelerated the reaction rate without compromising product enantiopurity. Key chemicals involved in the research include epichlorohydrin, 2,3-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, salicylaldehyde, Co(III) salen catalysts (1a and 1b), and AlCl3. The study also involved the synthesis of oximes and benzisoxazoles as part of the product characterization process.