1,3-Benzodioxole

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.

1,3-Benzodioxole
Kekulé, skeletal formula 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
Benzo[d][1,3]dioxole
1,2-[Methylenebis(oxy)]benzene
1,2-Methylenedioxybenzene
Identifiers
3D model (JSmol)
115506
ChEBI
ChemSpider
ECHA InfoCard 100.005.448
EC Number
  • 205-992-0
MeSH 1,3-Benzodioxole
RTECS number
  • DA5600000
UNII
UN number 1993
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Density 1.064 g cm−3
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 (ΔcH⦵298)
 -3.428 MJ mol−1
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H302, H332
NFPA 704 (fire diamond)
Flammability code 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 fuelHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
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 [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.[1]

Preparation

1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.[2][3]


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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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