Anisole

Structural formula
General
Surname	Anisole
other names	Methoxybenzene; Methoxybenzene; Methyl phenyl ether; Phenoxymethane;
Molecular formula	C 7 H 8 O
Brief description	colorless liquid with a pleasant odor
External identifiers / databases
EC number	202-876-1
ECHA InfoCard	100.002.615
PubChem	7519
ChemSpider	7238
Wikidata	Q312244
properties
Molar mass	108.14 g mol −1
Physical state	liquid
density	0.99 g cm −3 (20 ° C)
Melting point	−37 ° C
boiling point	154 ° C
Vapor pressure	3.6 hPa (20 ° C)
solubility	poor in water (0.14 g l −1 at 20 ° C); good in diethyl ether and ethanol ;
Dipole moment	1.38 (7) D (4.6 x 10 -30 C · m )
Refractive index	1.516 (20 ° C)
safety instructions
H and P phrases	H: 226-315-319
	P: 210-233-241-243-280-305 + 351 + 338
Toxicological data	3.7 g 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

Anisole is a characteristically smelling, colorless, flammable liquid. Since anisole can formally be understood as an ether made from phenol and methanol , it is also referred to as methylphenyl ether or methoxybenzene .

presentation

On a laboratory scale, anisole can be obtained by etherification of phenol or phenolates ( ether synthesis according to Williamson ), e.g. B. by reacting a phenolate with methyl iodide or phenol with dimethyl sulfate in the presence of a base .

use

Anisole is used as a solvent , a heat transfer medium (between 150 and 260 ° C) and a raw material for the synthesis of organic compounds such as drugs and fragrances .

Related structures

Name and structurally derived from Anis three other compounds ol by the introduction of a carbon atom from: anise alcohol, anise aldehyde, anise acid. The representation of anisaldehyde by means of Vilsmeier formylation .

	-CH ₂ OH	–CHO	-COOH

Anisole	Anise alcohol	Anisaldehyde	Anisic acid

The derivatives also include:

Anisolsulfonic acids
Phenetol (ethoxybenzene)
Anisidine (Aminoanisole)
Methyl anisoles
Nitro anisole
Thioanisole (phenol thioether)

IR spectrum of anisole

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on anisole in the GESTIS substance database of the IFA , accessed on March 17, 2017(JavaScript required) .
↑ Entry on anisole. In: Römpp Online . Georg Thieme Verlag, accessed on March 10, 2014.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dipole Moments, pp. 9-52.
↑ Anisole data sheet from Sigma-Aldrich , accessed on June 25, 2011 ( PDF ).

^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 345.

Web links

Commons : Anisol - collection of pictures, videos and audio files

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on anisole in the GESTIS substance database of the IFA , accessed on March 17, 2017(JavaScript required) .

[2] Entry on anisole. In: Römpp Online . Georg Thieme Verlag, accessed on March 10, 2014.

[CRC90_9_52-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dipole Moments, pp. 9-52.

[Sigma-4] Anisole data sheet from Sigma-Aldrich , accessed on June 25, 2011 ( PDF ).

[ORGANIKUM_19_345-5] Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 345.