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 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	115506
ChEBI	CHEBI:38732 Y
ChemSpider	13881169 Y
ECHA InfoCard	100.005.448
EC Number	205-992-0
MeSH	1,3-Benzodioxole
PubChem CID	9229
RTECS number	DA5600000
UNII	F0XLL582B8 Y
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 Y Key: FTNJQNQLEGKTGD-UHFFFAOYSA-N Y 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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H332
NFPA 704 (fire diamond)	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 [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]

See also

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