Thioanisole

Structural formula
General
Surname	Thioanisole
other names	Methylthiobenzene; Methyl phenyl sulfide; Thiophenol methyl ether;
Molecular formula	C 7 H 8 S
Brief description	colorless liquid with an unpleasant odor
External identifiers / databases
EC number	202-878-2
ECHA InfoCard	100.002.617
PubChem	7520
Wikidata	Q9087778
properties
Molar mass	124.21 g mol −1
Physical state	liquid
density	1.06 g cm −3
Melting point	−15 ° C
boiling point	195 ° C
solubility	very heavy in water (0.5 g l −1 at 25 ° C); miscible with most organic solvents;
Refractive index	1.5860 (20 ° C)
safety instructions
H and P phrases	H: 302-315-317-411
	P: 273-280-302 + 352
Toxicological data	891 mg 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

Thioanisole is a chemical compound from the group of thioethers and is a sulfur analogue of anisole .

Extraction and presentation

It can be made by the methylation of thiophenol .

It can also by alkylation of sodium thiophenolate with dimethyl sulfate are displayed or Trialkylammoniumiodid.

properties

Thioanisole is a colorless, flammable liquid with a characteristic, unpleasant odor that is very sparingly soluble in water.

use

Thioanisole is used as an intermediate in the manufacture of dyes, pharmaceuticals and agrochemicals. It is also used for the production of stable sulfonium salts , sulfoxides and sulfones and for the cleavage of methyl ethers in conjunction with trifluoromethanesulfonic acid . It also serves as a flavoring or adjuvant and is an important starting material for the synthesis of 3-substituted benzo [ b ] thiophenes. In the peptide synthesis , it is also used as an adjuvant (scavenger).

safety instructions

The vapors of methylphenyl sulfide can form an explosive mixture with air ( flash point 57 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on methylphenyl sulfide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c Data sheet Thioanisole, 99% from AlfaAesar, accessed on September 24, 2016 ( PDF )(JavaScript required) .
↑ Eberhard Breitmaier, Günther Jung: Organic chemistry basics, substance classes, reactions, concepts, molecular structures; 129 tables . Georg Thieme Verlag, 2005, ISBN 978-3-13-541505-5 , p. 412 ( limited preview in Google Book search).
^ NL Allinger: Organic Chemistry. [Main volume] Walter de Gruyter, 1980, ISBN 978-3-11-082970-9 , pp. 1584 ( limited preview in Google Book search).
↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 1370 ( limited preview in Google Book Search).
↑ Yi Yang: Side Reactions in Peptide Synthesis . Academic Press, 2015, ISBN 978-0-12-801181-2 , pp. 71 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on methylphenyl sulfide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Alfa-2] Data sheet Thioanisole, 99% from AlfaAesar, accessed on September 24, 2016 ( PDF )(JavaScript required) .

[Eberhard_Breitmaier,_Günther_Jung-3] Eberhard Breitmaier, Günther Jung: Organic chemistry basics, substance classes, reactions, concepts, molecular structures; 129 tables . Georg Thieme Verlag, 2005, ISBN 978-3-13-541505-5 , p. 412 ( limited preview in Google Book search).

[N.L._Allinger-4] NL Allinger: Organic Chemistry. [Main volume] Walter de Gruyter, 1980, ISBN 978-3-11-082970-9 , pp. 1584 ( limited preview in Google Book search).

[George_A._Burdock-5] George A. Burdock: Fenaroli's Handbook of Flavor Ingredients, Sixth Edition . CRC Press, 2016, ISBN 978-1-4200-9086-4 , pp. 1370 ( limited preview in Google Book Search).

[Yi_Yang-6] Yi Yang: Side Reactions in Peptide Synthesis . Academic Press, 2015, ISBN 978-0-12-801181-2 , pp. 71 ( limited preview in Google Book search).