4-Anisaldehyde

4-Anisaldehyde¹

Names
Preferred IUPAC name 4-Methoxybenzaldehyde
Other names 4-Anisaldehyde p-Anisaldehyde para-Anisaldehyde Anisic aldehyde Anise aldehyde
Identifiers
CAS Number	123-11-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28235
ChEMBL	ChEMBL161598 N
ChemSpider	28984 Y 21105937
ECHA InfoCard	100.004.185
EC Number	204-602-6
KEGG	C10761
PubChem CID	31244
UNII	9PA5V6656V Y
CompTox Dashboard (EPA)	DTXSID2026997
InChI InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 Key: ZRSNZINYAWTAHE-UHFFFAOYSA-N InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 Key: ZRSNZINYAWTAHE-UHFFFAOYAA
SMILES COc1ccc(C=O)cc1
Properties
Chemical formula	C8H8O2
Molar mass	136.150 g·mol−1
Density	1.119 g/cm32
Melting point	−1 °C (30 °F; 272 K)2
Boiling point	248 °C (478 °F; 521 K)2
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330, P501
Flash point	108 °C (226 °F; 381 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

4-Anisaldehyde, or p-Anisaldehyde, is an organic compound with the formula CH₃OC₆H₄CHO. The molecule consists of a benzene ring with a formyl and a methoxy group. It is a colorless liquid with a strong aroma. It provides sweet, floral and strong aniseed odor. Two isomers of 4-anisaldehyde are known, ortho-anisaldehyde and meta-anisaldehyde. They are less commonly encountered.

Anisaldehyde is prepared commercially by oxidation of 4-methoxytoluene (p-cresyl methyl ether) using manganese dioxide to convert a methyl group to the aldehyde group. It can also be produced by oxidation of anethole, a related fragrance that is found in some alcoholic beverages, by oxidative cleavage of an alkene.³

Being structurally related to vanillin, 4-anisaldehyde is widely used in the fragrance and flavour industry.³ It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. The related ortho isomer has a scent of liquorice.

In perfumery, it is particularly used in hawthorn, lilac, and cherry blossom accords because of its good tenacity. It also serves as a key intermediate in the synthesis of the antibiotic amoxicillin⁴.

A solution of para-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography.⁵ Different chemical compounds on the plate can give different colors, allowing easy distinction.