5780-00-7

Basic information

• Product Name: 6-METHOXY-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE
• Synonyms: CHEMBRDG-BB 4015071;6-METHOXY-1,3-BENZODIOXOLE-5-CARBALDEHYDE;6-METHOXY-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE;6-methoxy-1,3-benzodioxole-5-carbaldehyde(SALTDATA: FREE);5-Formyl-6-methoxy-1,3-benzodioxole;6-Methoxypiperonal;6-methoxybenzo[d][1,3]dioxole-5-carbaldehyde;1,3-Benzodioxole-5-carboxaldehyde,6-methoxy-
• CAS NO: 5780-00-7
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• Mol File: 5780-00-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 109-115°C
• Boiling Point: 302.5°C at 760 mmHg
• Flash Point: 134.4°C
• Appearance: /
• Density: 1.321g/cm³
• Vapor Pressure: 0.000984mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-METHOXY-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE(5780-00-7)
• EPA Substance Registry System: 6-METHOXY-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE(5780-00-7)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5780-00-7(Hazardous Substances Data)

Usage

General Description

6-Methoxy-benzo[1,3]dioxole-5-carbaldehyde is a chemical compound with the molecular formula C9H8O3. It is a highly aromatic aldehyde that contains a methoxy group and a dioxole ring. 6-METHOXY-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE is commonly used in the synthesis of various pharmaceuticals and agrochemicals. It has also been found to exhibit antimicrobial and antioxidant properties, making it an important compound in the development of new drugs and food additives. Additionally, 6-methoxy-benzo[1,3]dioxole-5-carbaldehyde is considered to be a potential precursor in organic synthesis for further chemical reactions to form more complex molecules.

InChI:InChI=1/C9H8O4/c1-11-7-3-9-8(12-5-13-9)2-6(7)4-10/h2-4H,5H2,1H3

Upstream product

• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 7228-35-5 5-methoxybenzo[d]1,3-dioxole 
• 4885-02-3 Dichloromethyl methyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 10022-35-2 1-bromo-2-methoxy-4,5-methylenedioxybenzene 
• 533-31-3 Sesamol 
• 120-57-0 piperonal 
• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 23126-68-3 6-amino-benzo[1,3]dioxole-5-carbaldehyde 

Downstream Products

• 10338-24-6 4-(6-methoxy-benzo[1,3]dioxol-5-ylmethylene)-2-phenyl-4H-oxazol-5-one 
• 4383-14-6 2-methoxy-4,5-methylenedioxyphenylmethyl alcohol 
• 88755-20-8 2-methoxy-4,5;3'4'-bis(methylenedioxy)chalcone 
• 73827-95-9 5-(1-hydroxy-4-pentenyl)-6-methoxy-1,3-benzodioxole 
• 74660-20-1 (E)-ethyl 3-(6-methoxybenzo[d][1,3]dioxol-5-yl)acrylate 
• 64635-44-5 ethyl 2-methoxypiperate 
• 73827-97-1 allyl-3-hydroxy-3-(2-methoxy-4,5-methylenedioxyphenyl)-propionate 
• 67879-91-8 2-methoxy-4,5-methylenedioxy-trans-cinnamoyl piperidide 
• 82682-47-1 2-methoxy-4',5'-methylenedioxy-trans-cinnamoylpyrrolidine 
• 107023-00-7 (3R,4S)-4-ethenyl-3-<(1R/S)-1-hydroxy-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl>dihydro-2(3H)-furanone 
• 88775-64-8 2,3',4'-trimethoxy-4,5-methylenedioxychalcone 
• 107914-30-7 2-(2-methoxy-4,5-methylenedioxyphenyl)-1-(methylsulfinyl)-1-(methylthio)ethylene 
• 21505-18-0 2-methoxy-4,5-methylenedioxyphenol 
• 5689-99-6 4,5-dihydroxy-2-methoxy-benzaldehyde 

Relevant articles and documents

Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis

A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 μM and 16.40 μM, respectively. The intracellular amastigotes assays showed IC50 = 22.00 μM (22) and 17.00 μM (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase.

Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues

Routes were investigated for the synthesis of cicerfuran, a hydroxylated benzofuran from wild chickpea implicated in resistance to Fusarium wilt, and some of its analogues. A novel method is described for the synthesis of oxygenated benzofurans by epoxidation and cyclisation of 2′-hydroxystilbenes. The stilbene intermediates required could be synthesised by palladium-catalysed coupling of styrenes with mono-oxygenated aryl halides but not with di-oxygenated aryl halides. Stilbenes corresponding to the latter were synthesised by Wittig reactions.

Total Synthesis of Carpacin and Its Geometric Isomer as a Cancer Chemopreventer

Carpacin (1a), an antidepressant in Asiatic folk medicine from the Carpano tree, is achieved in which the longest linear sequence is only four steps in over all yield 67 percent from commercially available Sesamol. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions of aryl bromide with Grignard reagents. The first preparation of its geometric isomer (1b) is described. Highlights of the synthesis include Pd-ctalyzed coupling, selective hydrogenation, and Wittig reactions. Carpacin was examined as a potential inhibitor of carcinogenesis.