1,3-Benzodioxole

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
CAS Number	274-09-9 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	115506
ChEBI	CHEBI:38732 ;
ChemSpider	13881169 ;
ECHA InfoCard	100.005.448
EC Number	205-992-0;
MeSH	1,3-Benzodioxole
PubChem CID	9229;
RTECS number	DA5600000;
UNII	F0XLL582B8 ;
UN number	1993
CompTox Dashboard (EPA)	DTXSID9051951 ;
	InChI InChI=1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 Key: FTNJQNQLEGKTGD-UHFFFAOYSA-N ; InChI=1/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2 Key: FTNJQNQLEGKTGD-UHFFFAOYAV;
	SMILES C1Oc2ccccc2O1; C1OC2=C(O1)C=CC=C2;
Properties
Chemical formula	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)	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).
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	Infobox references

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.[1]

Preparation

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

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References

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
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.
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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[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.

1,3-Benzodioxole

Preparation

See also

References