1,3-Benzodioxole

Base Information

• Chemical Name: 1,3-Benzodioxole
• CAS No.: 274-09-9
• Molecular Formula: C7H6O2
• Molecular Weight: 122.123
• Hs Code.: 29329970
• European Community (EC) Number: 205-992-0
• NSC Number: 30095
• UNII: F0XLL582B8
• DSSTox Substance ID: DTXSID9051951
• Nikkaji Number: J25.405C
• Wikipedia: 1,3-Benzodioxole
• Wikidata: Q3544944
• Metabolomics Workbench ID: 55988
• ChEMBL ID: CHEMBL4757380
• Mol file: 274-09-9.mol

Synonyms:1,3-benzodioxole;methylene dioxybenzene;methylenedioxybenzene

Chemical Property of 1,3-Benzodioxole

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 12 mm Hg ( 25 °C)
• Melting Point: -18 °C
• Refractive Index: n20/D 1.539(lit.)
• Boiling Point: 173 °C at 760 mmHg
• Flash Point: 55 °C
• PSA: 18.46000
• Density: 1.213 g/cm³
• LogP: 1.41530
• Storage Temp.: -20°C
• Solubility.: 2g/l
• Water Solubility.: 0.2 g/100 mL (25 ºC)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 122.036779430
• Heavy Atom Count: 9
• Complexity: 91.1

Purity/Quality:

99% ^*data from raw suppliers

1,3-Benzodioxole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/22-22-10-36/37/38-20/21/22-10/22
• Safety Statements: 23-24/25-36/37/39-26-16-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1OC2=CC=CC=C2O1
• Description: 1,3-Benzodioxole, widely found in plant products, has shown potent antioxidant and antibacterial activities. It has recently been reported that 1,3-benzodioxole derivatives possess cytotoxic activity against several human tumor cell lines, including human colon carcinoma cells and multidrug-resistant nasopharyngeal carcinoma cells. No cytotoxic effects were noticed at a concentration of 10-4 M.
• Uses: 1,3-Benzodioxole is useful in gemological stimulant detection. It is also used as a precursor for perfumes, photo initiators, agrochemicals and pharmaceuticals. 1,3-benzodimine is an intermediate for the synthesis of the drugs oxolinic acid, cinoxacin and miloxacin.

Technology Process of 1,3-Benzodioxole

There total 48 articles about 1,3-Benzodioxole 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: 100.0%

5-chloro-1,3-benzodioxole (7228-38-8) → Methylenedioxybenzene (274-09-9)

Guidance literature:

With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon; In 1,2-dichloro-ethane; at 50 ℃; for 5h;

DOI:10.1002/adsc.201901099

Reference yield: 99.0%

3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) → Methylenedioxybenzene (274-09-9)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; tetrahydroxydiboron; 1,3-bis(bis(4-methoxyphenyl)phosphino)propane; In water; 1,2-dichloro-ethane; at 70 ℃; for 0.25h;

DOI:10.1002/anie.201906148

Reference yield: 96.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → Methylenedioxybenzene (274-09-9)

Guidance literature:

With potassium phosphate; In N,N-dimethyl-formamide; cyclohexanol; at 110 ℃; for 12h;

DOI:10.1016/j.jorganchem.2013.12.053

upstream raw materials:

5,6-dibromo-1,3-benzodioxole

diiodomethane

benzene-1,2-diol

dichloromethane

Downstream raw materials:

5-nitro-1,3-benzodioxole

ethyl 1,3-benzodioxole-5-carboxylate

benzene-1,2-diol

5-chloro-1,3-benzodioxole

Refernces

• 1、 Tan, Boon-Hong,Yoshikai, Naohiko. "Cobalt-catalyzed addition of arylzinc reagents to norbornene derivatives through 1,4-cobalt migration". . p. 3392 - 3395. Retrieved 2014.
• 2、 -. "A method of synthesis of piperonolamine". Paragraph 0144-0147; 0157-0160. . Retrieved 2022/01/07.
• 3、 Caner, Joaquim,Iwasawa, Nobuharu,Martin, Ruben,Murata, Kei,Shimomaki, Katsuya,Toriumi, Naoyuki. "Mechanistic studies into visible light-driven carboxylation of aryl halides/triflates by the combined use of palladium and photoredox catalysts". supporting information. p. 1846 - 1853. Retrieved 2021/08/13.