3,4-Dimethoxybenzaldehyde

Base Information

• Chemical Name: 3,4-Dimethoxybenzaldehyde
• CAS No.: 120-14-9
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29124900
• European Community (EC) Number: 204-373-2
• NSC Number: 24521,8500
• UNII: UI88P68JZD
• DSSTox Substance ID: DTXSID7026285
• Nikkaji Number: J9.907D
• Wikipedia: Veratraldehyde
• Wikidata: Q414395
• Metabolomics Workbench ID: 45286
• ChEMBL ID: CHEMBL1088937
• Mol file: 120-14-9.mol

Synonyms:3,4-dimethoxybenzaldehyde;veratraldehyde

Chemical Property of 3,4-Dimethoxybenzaldehyde

Chemical Property:

• Appearance/Colour: needle-shaped crystal
• Vapor Pressure: 0.00366mmHg at 25°C
• Melting Point: 42-45 ºC
• Refractive Index: 1.534
• Boiling Point: 281 ºC at 760 mmHg
• Flash Point: 110.4ºC
• PSA: 35.53000
• Density: 1.114 g/cm³
• LogP: 1.51630
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: alcohol: freely soluble
• Water Solubility.: <0.1 g/100 mL at 22℃
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dimethoxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-38-36/37/38-36/38
• Safety Statements: 26-22-24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=O)OC
• Description: 3,4-Dimethoxybenzaldehyde is an organic compound found in various natural sources such as Wisteria floribunda, Zingiber montanum, and other organisms. It typically appears as white or milky white needle-like crystals with a vanilla bean aroma or as white or pale yellow flaky crystals with the scent and sweetness of vanilla fruit. This compound is easily soluble in ethanol and ether but sensitive to air, prone to oxidation to form 3,4-dimethoxybenzoic acid when exposed to light.^[1]
• Uses: In the chemical industry, 3,4-dimethoxybenzaldehyde serves as a crucial intermediate for organic synthesis with diverse applications. One significant application is its use in the production of the veterinary drug sulfonamide synergist Dimethonium (DVD). This drug, incorporated into animal feed at 0.02% (by weight), enhances the effectiveness of iodine-based medications in preventing and treating bacterial infections in poultry. Additionally, 3,4-dimethoxybenzaldehyde plays a role in sulfate formation via aerosol-phase SO2 oxidation by biomass-burning-derived aromatic carbonyl photosensitizers.^[3] Its participation in photosensitized oxidation of sulfur dioxide (SO2) in aerosols contributes to sulfate formation in the atmosphere, especially in regions influenced by biomass burning. Moreover, 3,4-dimethoxybenzaldehyde exhibits repellent properties against mosquito females and tick nymphs, suggesting its potential application as a commercial repellent agent against arthropod-borne infectious pests.^[2]
• References: [1] Study on the volatility of four benzaldehydes; DOI 10.1016/j.tca.2022.179357; [2] Repellency of Veratraldehyde (3,4-Dimethoxy Benzaldehyde) against Mosquito Females and Tick Nymphs; DOI 10.3390/app11114861; [3] Sulfate formation via aerosol-phase SO2 oxidation by model biomass burning photosensitizers: 3,4-dimethoxybenzaldehyde, vanillin and syringaldehyde using single-particle mixing-state analysis

Technology Process of 3,4-Dimethoxybenzaldehyde

There total 514 articles about 3,4-Dimethoxybenzaldehyde 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: 60.0%

1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)-propane-1,3-diol → 4-methoxy-benzaldehyde (123-11-5) + 3,4-dimethoxy-benzaldehyde (120-14-9) + 4-methoxybenzoic acid (100-09-4) + Veratric acid (93-07-2)

Guidance literature:

With oxygen; In acetonitrile; for 8h; under 760.051 Torr; Irradiation;

DOI:10.1021/acscatal.8b00022

Reference yield: 52.0%

1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanol (17078-88-5) → 2-methoxyphenoxy-3',4'-dimethoxyacetophenone (22675-96-3) + 3,4-dimethoxy-benzaldehyde (120-14-9) + 2-methoxy-phenol (90-05-1)

Guidance literature:

With 3C₆H₁₂N₂*Fe⁽³⁺⁾*3Cl^(1-); dihydrogen peroxide; acetic acid; In water; dimethyl sulfoxide; at 100 ℃; for 16h;

DOI:10.1039/c5gc01306b

Reference yield: 31.4%

1,2-bis(3,4-dimethoxyphenyl)-1,3-propanediol (41564-97-0) → 1,2-bis(3,4-dimethoxyphenyl)ethane-1,2-dione (554-34-7) + 3,4-dimethoxy-benzaldehyde (120-14-9) + Veratric acid (93-07-2)

Guidance literature:

With bis(acetylacetonate)oxovanadium; oxygen; acetic acid; In water; acetonitrile; at 100 ℃; for 48h; Reagent/catalyst; Solvent;

DOI:10.1039/c8ob00409a

upstream raw materials:

3,4-dihydroxybenzaldehyde

methyl iodide

1,2-dimethoxy-4-methylbenzene

(3,4-dimethoxyphenyl)methanol

Downstream raw materials:

veratronitrile

(3-morpholino-propyl)-veratryl-amine

α-Veratryliden-γ-butyrolacton

(5-piperidino-pentyl)-veratryl-amine

Refernces

• 1、 Fathalla, Walid,Pazdera, Pavel,El-Rayes, Samir,Ali, Ibrahim.A.I.. "Efficient synthesis of α-substituted-α-arylmethyl phosphonates using trichloroacetimidate C–C coupling method". . p. 1681 - 1691. Retrieved 2018.
• 2、 Hajipour,Mallakpour,Adibi. "Oxidation of alcohols with benzyltriphenylphosphonium peroxymonosulfate under non-aqueous conditions". . p. 71 - 79. Retrieved 2000.
• 3、 Weijlard,Tashjian,Tishler. "-". . p. 2070. Retrieved 1947.
• 4、 Rashid, Goran M. M.,Zhang, Xiaoyang,Wilkinson, Rachael C.,Fül?p, Vilmos,Cottyn, Betty,Baumberger, Stéphanie,Bugg, Timothy D. H.. "Sphingobacterium sp. T2 Manganese Superoxide Dismutase Catalyzes the Oxidative Demethylation of Polymeric Lignin via Generation of Hydroxyl Radical". . p. 2920 - 2929. Retrieved 2018.
• 5、 Sharma, Meenakshi,Ray. "Synthesis and biological evaluation of amide derivatives of (5,6-dimethoxy-2,3-dihydro-1H-inden-1-yl)acetic acid as anti-inflammatory agents with reduced gastrointestinal ulcerogenecity". . p. 2092 - 2102. Retrieved 2008.
• 6、 Yuasa, Yoshifumi,Shibuya, Shiroshi,Yuasa, Yoko. "The Oxidation of 3-Aryl-1-propenes by Oxidative System of RuCl 3-NaIO4-Phase Transfer Catalyst". . p. 3947 - 3952. Retrieved 2003.
• 7、 D'Alfonso, Claudio,Lanzalunga, Osvaldo,Lapi, Andrea,Vadalà, Raffaella. "Comparing the catalytic efficiency of ring substituted 1- hydroxybenzotriazoles as laccase mediators". . p. 3049 - 3055. Retrieved 2014.
• 8、 Capdevielle, Patrice,Maumy, Michel. "ORTHO-HYDROXYLATION SELECTIVE DES PHENOLS : II - UN NOUVEAU SYSTEME CATALYTIQUE A CARACTERE PREPARATIF.". . p. 1577 - 1580. Retrieved 1982.
• 9、 Harwood,Johnson. "-". . p. 2555,2557. Retrieved 1933.
• 10、 Asghedom,LaLonde,Ramdayal. "Structural requirements for ipso-nitration with cerium(IV) ammonium nitrate (CAN)". . p. 3989 - 3991. Retrieved 2002.