1,2-methylenedioxybenzene

Structural formula
General
Surname	1,2-methylenedioxybenzene
other names	1,2- (methylenedioxy) benzene 1,3-benzodioxole 1,3-dioxindane
Molecular formula	C 7 H 6 O 2
Brief description	light yellow clear liquid
External identifiers / databases
CAS number 274-09-9 EC number 205-992-0 ECHA InfoCard 100.005.448 PubChem 9229 Wikidata Q3544944
properties
Molar mass	122.12 g mol −1
Physical state	liquid
density	1.064 g cm −3 (25 ° C)
Melting point	-18 ° C
boiling point	172-173 ° C
Vapor pressure	16 hPa (25 ° C)
solubility	sparingly soluble in water (2 g l −1 at 25 ° C)
Refractive index	1,539
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-332 P: no P-phrases
Toxicological data	580 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,2-Methylenedioxybenzene is a chemical compound from the group of dioxoles .

Extraction and presentation

1,2-Methylenedioxybenzene is obtained from piperonal by decarbonylation .

It can also be represented by the methylenation of catechol with sodium hydroxide and dichloromethane in dimethyl sulfoxide . The sodium hydroxide deprotonates the phenol groups of the catechol, the phenolate formed is a strong nucleophile and can thus react with the dichloromethane.

${\displaystyle \mathrm {C_{6}H_{4}(OH)_{2}+2\ NaOH\longrightarrow 2\ C_{6}H_{4}(ONa)_{2}+2\ H_{2}O} }$

${\displaystyle \mathrm {C_{6}H_{4}(ONa)_{2}+CH_{2}Cl_{2}\longrightarrow 2\ C_{6}H_{4}O_{2}CH_{2}+2\ NaCl} }$

use

1,3-Benzodioxole is a raw material for the synthesis of, for example, podophyllotoxin and oxolinic acid .

Individual evidence

1. ↑ ^{a b c d e f g h i} Data sheet 1,3-Benzodioxole, 99% from Sigma-Aldrich , accessed on February 27, 2014 ( PDF ).
2. ↑ ^{a b} Entry on 1,3-Benzodioxole at ChemicalBook , accessed on February 27, 2014.
3. ↑ F. Dallacker, R. Binsack: Note on the representation of methylenedioxybenzene. In: Monthly magazine for chemistry . 92, 1961, pp. 492-493, doi : 10.1007 / BF01153904 . ( PDF )
4. ↑ https://erowid.org/archive/rhodium/chemistry/methylenation.html