4-methoxyacetophenone

Structural formula
General
Surname	4-methoxyacetophenone
other names	1- (4-methoxyphenyl) ethanone ( IUPAC ); p -acetanisole; p -acetylanisole; p -methoxyphenyl methyl ketone; METHOXYACETOPHENONE ( INCI ) ;
Molecular formula	C 9 H 10 O 2
Brief description	colorless, pleasantly smelling tablets
External identifiers / databases
EC number	202-815-9
ECHA InfoCard	100.002.560
PubChem	7476
ChemSpider	13835344
Wikidata	Q229995
properties
Molar mass	150.18 g mol −1
Physical state	firmly
density	1.08 g cm −3
Melting point	38 ° C
boiling point	263 ° C
Vapor pressure	6.44 Pa (20 ° C)
solubility	poor in water (2.47 g l −1 at 25 ° C), good in ethanol
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315
	P: no P-phrases
Toxicological data	1720 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , percutaneous ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-methoxyacetophenone , also p -acetylanisole or acetanisole for short , is a methyl ketone of anisole . The structure is derived from that of anisole and also has an acetyl group in the para position to the methoxy group . It has a pleasantly sweet smell, similar to that of hawthorn flowers or anisaldehyde .

Occurrence and use

In nature it occurs in Bibergeil , a glandular secretion of the beaver . It is a secondary component of medicines and is used as a fragrance , for example in deodorants.

presentation

Acetanisole is synthesized from anisole and acetyl chloride in a Friedel-Crafts acylation :

A more environmentally friendly alternative to using aluminum trichloride as a catalyst for Friedel-Crafts acylation is catalysis with zeolites .

properties

Acetanisole is a colorless, crystalline substance with a sweet odor. The crystals melt at low temperatures (approx. 38 ° C).

toxicology

In studies with rats and rabbits , LD ₅₀ values of 1720 mg kg ⁻¹ (oral) and> 5000 mg kg ⁻¹ ( percutaneous ) were determined. In studies in 1985 with humans and mice, the substance produced an increase in pulse rate and blood pressure in humans and drowsiness and muscle weakness in mice.

Individual evidence

↑ Entry on METHOXYACETOPHENONE in the CosIng database of the EU Commission, accessed on March 21, 2020.
↑ ^a ^b ^c ^d ^e Entry on 4-methoxyacetophenone. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
↑ ^a ^b ^c ^d ^e Entry on 4-methoxyacetophenone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Data sheet 4′-Methoxyacetophenone from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
↑ Christoph Meier: "Green Chemistry" - from the beginning in "Science Life" at ETH Zurich .
↑ Gigiena i Sanitariya / HYSAAV , 1985 , 50 (4), p. 86.

[CosIng-1] Entry on METHOXYACETOPHENONE in the CosIng database of the EU Commission, accessed on March 21, 2020.

[Römpp-2] Entry on 4-methoxyacetophenone. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[ChemIDplus-3] Entry on 4-methoxyacetophenone in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-4] Data sheet 4′-Methoxyacetophenone from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).

[5] Christoph Meier: "Green Chemistry" - from the beginning in "Science Life" at ETH Zurich .

[6] Gigiena i Sanitariya / HYSAAV , 1985 , 50 (4), p. 86.