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
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

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]

See also

• 1,4-Benzodioxine
• Methylenedioxy
• Safrole
• Piperonal

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.