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1,3-Benzodioxole

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1,3-Benzodioxole
Kekulé, skeletal formula of 1,3-benzodioxole
Kekulé, skeletal formula of 1,3-benzodioxole
Ball and stick model of 1,3-benzodioxole
Ball and stick model of 1,3-benzodioxole
Names
Preferred IUPAC name 2H-1,3-Benzodioxole
Other names 1,3-Benzodioxole
Benzodioxole
1,2-benzene
1,2-Methylenedioxybenzene
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 115506
ChEBI
ChemSpider
ECHA InfoCard 100.005.448 Edit this at Wikidata
EC Number
  • 205-992-0
MeSH 1,3-Benzodioxole
PubChem CID
RTECS number
  • DA5600000
UNII
UN number 1993
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2Key: FTNJQNQLEGKTGD-UHFFFAOYSA-N
  • InChI=1/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2Key: FTNJQNQLEGKTGD-UHFFFAOYAV
SMILES
  • C1Oc2ccccc2O1
  • C1OC2=C(O1)C=CC=C2
Properties
Chemical formula C7H6O2
Molar mass 122.123 g·mol
Density 1.064 g cm
Boiling point 172–173 °C (342–343 °F; 445–446 K)
log P 2.08
Vapor pressure 1.6 kPa
Thermochemistry
Std enthalpy of
combustion (ΔcH298) 		-3.428 MJ mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H332
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 2 0
Flash point 61 °C (142 °F; 334 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula C6H4O2CH2. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid.

Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.

Preparation

1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.

See also

References

  1. Murray, M., "Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation", Curr. Drug Metab. 2000, volume 1, 67-84. doi:10.2174/1389200003339270
  2. Bonthrone, W. & Cornforth, J. (1969). "The methylenation of catechols". Journal of the Chemical Society (9): 1202–1204. doi:10.1039/J39690001202. Retrieved 28 December 2013.
  3. Fujita, Harushige; Yamashita & Masataro (1973). "The Methylenation of Several Allylbenzene-1,2-diol Derivatives in Aprotic Polar Solvents". Bulletin of the Chemical Society of Japan. 46 (11): 3553–3554. doi:10.1246/bcsj.46.3553. Retrieved 27 December 2013.


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