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Piperonal

Piperonal

IUPAC name	1,3-benzodioxole-5-carbaldehyde
Other names	heliotropine
Identifiers
CAS number	120-57-0
SMILES	O=Cc1ccc2OCOc2c1
Properties
Molecular formula	C₈H₆O₃
Molar mass	150.13 g/mol
Melting point	35-37 °C
Boiling point	264 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Piperonal (heliotropine, protocatechuic aldehyde methylene ether) is an aromatic aldehyde that comes as transparent crystals, C₈H₆O₃, and has a floral odor. It is used as flavoring and in perfume. It can be obtained by oxidation of piperonyl alcohol. It is also a minor natural component of the extract of vanilla.

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It may be used in the synthesis of 3,4-methylenedioxyamphetamine (MDA). In one synthetic path, nitroethane in a glacial acetic acid solution with an ammonium acetate catalyst yields a substituted nitrostyrene via a condensation reaction. This intermediate can then be reduced in the presence of a strong reducing agent such as lithium aluminum hydride (LiAlH₄) to yield MDA.