Thioacetic acid

Structural formula
General
Surname	Thioacetic acid
other names	Thiolacetic acid
Molecular formula	C 2 H 4 OS
Brief description	colorless to yellowish liquid with a penetrating pungent odor
External identifiers / databases
EC number	208-063-8
ECHA InfoCard	100.007.331
PubChem	10484
ChemSpider	10052
Wikidata	Q423721
properties
Molar mass	76.12 g mol −1
Physical state	liquid
density	1.07 g cm −3 (20 ° C)
Melting point	−17 ° C
boiling point	86-88 ° C
Vapor pressure	1.07 h Pa (20 ° C)
pK s value	3.33 (25 ° C)
solubility	27 g · l −1 in water (15 ° C) with slow decomposition
Refractive index	1.4648 (20 ° C)
safety instructions
H and P phrases	H: 225-301-317-318
	P: 210-280-301 + 310-330-305 + 351 + 338-333 + 313-370 + 378
Thermodynamic properties
ΔH f 0	−216.9 kJ / mol
	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

Thioacetic acid is an organic compound. It has the same structure as acetic acid , but the oxygen atom of the hydroxyl group has been replaced by sulfur .

properties

Thioacetic acid has a lower boiling point than acetic acid. Thioacetic acid is a colorless to yellow liquid that smokes in the air and has a pungent, unpleasant, and if sufficiently diluted, fruity odor. Their vapors irritate and damage the eyes, respiratory tract, lungs and skin.

synthesis

When glacial acetic acid is heated with phosphorus (V) sulfide , thioacetic acid is formed. Alternatively, thioacetic acid can be made from acetic anhydride and hydrogen sulfide . A synthesis from acetyl chloride and hydrogen sulfide is also described.

use

It is used in organic chemistry for the introduction of thiol groups into molecules. It is also used to destroy peroxides as an alternative to aqueous reducing agents .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on thioacetic acid in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-42.
↑ Data sheet thioacetic acid (PDF) from Merck , accessed on April 24, 2011.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-484.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-22.
^ Römpp Chemie Lexikon, Thieme Verlag Stuttgart, 9th edition, Volume 6, p. 4585.
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1602, ISBN 978-0-911910-00-1 .
↑ Alfons Schöberl and Annemarie Wagner in Houben-Weyl Methods of Organic Chemistry , edited by Eugen Müller, Otto Bayer , Hans Meerwein and Karl Ziegler , Volume 9, Sulfur , Selenium and Tellurium compounds , Thieme Verlag, Stuttgart, 1955, there 741-771.

[gestis-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on thioacetic acid in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CRC90_8_42-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-42.

[merck-3] Data sheet thioacetic acid (PDF) from Merck , accessed on April 24, 2011.

[CRC90_3_484-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-484.

[CRC90_5_22-5] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-22.

[RoemppChemieLexikon-6] Römpp Chemie Lexikon, Thieme Verlag Stuttgart, 9th edition, Volume 6, p. 4585.

[MerckIndex-7] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1602, ISBN 978-0-911910-00-1 .

[Schöberl-8] Alfons Schöberl and Annemarie Wagner in Houben-Weyl Methods of Organic Chemistry , edited by Eugen Müller, Otto Bayer , Hans Meerwein and Karl Ziegler , Volume 9, Sulfur , Selenium and Tellurium compounds , Thieme Verlag, Stuttgart, 1955, there 741-771.