2-Hydroxy-3-methoxybenzaldehyde

Base Information

• 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

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

Chemical Property of 2-Hydroxy-3-methoxybenzaldehyde

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): Xn,Xi
• 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
• Uses: A positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin. o-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII). It is also used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals. o-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII).

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:

Reference yield: 98.0%

2-hydroxy-3-methoxybenzyl alcohol (4383-05-5) → 3-methoxy-2-hydroxybenzaldehyde (148-53-8)

Guidance literature:

In neat (no solvent); at 20 ℃; for 0.0333333h; Microwave irradiation;

DOI:10.33224/rrch.2020.65.3.08

Reference yield: 98.0%

2,3-dimethyoxybenzaldehyde (86-51-1) → 3-methoxy-2-hydroxybenzaldehyde (148-53-8)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; for 22h; Heating;

DOI:10.1055/s-1989-27225

Reference yield: 84.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate (217813-03-1) → 3-methoxy-2-hydroxybenzaldehyde (148-53-8)

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

upstream raw materials:

3-methoxy-2-methoxycarbonyloxy-benzoyl chloride

1,3,5-tris(o-tolyl)-hexahydro-s-triazine

2-methoxy-phenol

1,3,5-tris-(4-ethoxy-phenyl)-hexahydro-[1,3,5]triazine

Downstream raw materials:

2-hydroxy-3-methoxy-5-morpholinomethyl-benzaldehyde ; hydrochloride

2-methoxy-6-(((4-methoxyphenyl)imino)methyl)phenol

(2-hydroxy-3-methoxy-phenyl)-acetic acid

4-((Z)-2-acetoxy-3-methoxy-benzylidene)-2-phenyl-4H-oxazol-5-one

Refernces

• 1、 Muche, Simon,Levacheva, Irina,Samsonova, Olga,Biernasiuk, Anna,Malm, Anna,Lonsdale, Richard,Popio?ek, ?ukasz,Bakowsky, Udo,Ho?yńska, Ma?gorzata. "Synthesis, structure and stability of a chiral imine-based Schiff-based ligand derived from L-glutamic acid and its [Cu4] complex". . p. 231 - 236. Retrieved 2017.
• 2、 Alam, Md. Iqbal,Alam, Mohammed A.,Alam, Ozair,Nargotra, Amit,Taneja, Subhash Chandra,Koul, Surrinder. "Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship". . p. 209 - 219. Retrieved 2016.
• 3、 Yu, Qishun,Lu, Chengrong,Zhao, Bei. "Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth-Metal Complexes Supported with Phenoxy-Functionalized TsDPEN Ligands". supporting information. p. 2529 - 2537. Retrieved 2021/07/28.
• 4、 AHMADI, Sayed Ali,GHALEHBANDI, Shermineh Sadat,GHAZANFARI, Dadkhoda,SHEIKHHOSSEINI, Enayatollah. "Solvent-free, microwave assisted oxidation of alcohols with 4-hydroxypyridinium chlorochromate functionalized silica gel". . p. 283 - 289. Retrieved 2020/10/06.