4-Methylacetophenone

4-Methylacetophenone
	source ↗
Names
	IUPAC name 1-(4-methylphenyl)ethanone
	Other names p-Methylacetophenone; p-Acetyltoluene
Identifiers
CAS Number	122-00-9 Y;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:178626;
ChEMBL	ChEMBL271871;
ChemSpider	8186;
ECHA InfoCard	100.004.105
EC Number	204-514-8;
PubChem CID	8500;
UNII	AX66V0KX3Y;
CompTox Dashboard (EPA)	DTXSID9044374 ;
	InChI InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3 Key: GNKZMNRKLCTJAY-UHFFFAOYSA-N;
	SMILES CC1=CC=C(C=C1)C(=O)C;
Properties
Chemical formula	C9H10O
Molar mass	134.178 g·mol−1
Appearance	white or colorless oil
Density	1.006 g/cm3
Melting point	28 °C (82 °F; 301 K)
Boiling point	224 °C (435 °F; 497 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H315
Precautionary statements	P264, P270, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Methylacetophenone is an organic compound with the formula CH₃C₆H₄C(O)CH₃. It is related to acetophenone with a methyl group at the 4-position. Two isomers, 2-methylacetophenone and 3-methylacetophenone, are also known. It is a fragrance of commercial significance.¹

Synthesis and reactions

It is prepared by acetylation of toluene.²

Oxidation with hot nitric acid followed by potassium permanganate gives terephthalic acid.³ It undergoes most of the reactions of acetophenone: reduction to the alcohol followed by dehydration gives 4-methylstyrene.

Occurrence

4-Methylacetophenone occurs naturally in some woods.

References

Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
Röper, Michael; Gehrer, Eugen; Narbeshuber, Thomas; Siegel, Wolfgang (2000). "Acylation and Alkylation". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_185. ISBN 978-3-527-30385-4.
C. F. Koelsch (1946). "Terephthalic Acid". Organic Syntheses. 26: 95. doi:10.15227/orgsyn.026.0095.

[1] Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.

[2] Röper, Michael; Gehrer, Eugen; Narbeshuber, Thomas; Siegel, Wolfgang (2000). "Acylation and Alkylation". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_185. ISBN 978-3-527-30385-4.

[3] C. F. Koelsch (1946). "Terephthalic Acid". Organic Syntheses. 26: 95. doi:10.15227/orgsyn.026.0095.

1

2

3