Thiodiglycolic acid

Structural formula
General
Surname	Thiodiglycolic acid
other names	Thiodi (acetic acid); Thiodiglycolic acid; 2,2′-thiobis (acetic acid); Bis (carboxymethyl) sulfide; TDGS; TDGA;
Molecular formula	C 4 H 6 O 4 S
Brief description	beige powder with an unpleasant odor
External identifiers / databases
EC number	204-663-9
ECHA InfoCard	100.004.241
PubChem	31277
Wikidata	Q15632885
properties
Molar mass	150.15 g mol −1
Physical state	firmly
Melting point	128-131 ° C
solubility	easily soluble in water (400 g l −1 at 18 ° C) and ethanol; soluble in benzene;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
Toxicological data	> 2000 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 .

Thiodiglycolic acid is an organic compound. It consists of two acetic acid groups that are linked by a sulfur bridge.

Extraction

Thiodiglycolic acid is obtained from hydrogen sulfide and sodium chloroacetate :

{\ displaystyle \ mathrm {H_ {2} S + 2 \ ClCH_ {2} CO_ {2} Na \ rightarrow S (CH_ {2} COOH) _ {2} +2 \ NaCl}}

properties

Thiodiglycolic acid is a flammable beige solid with an unpleasant odor that is easily soluble in water. Your aqueous solution reacts strongly acidic.

use

Thiodiglycolic acid is used as a detection reagent for copper, lead, mercury and silver.

The salts of thiodiglycolic acid are called thiodiglycolates and are used in many ways. Dibutyl thioglycolate is a raw material for the synthesis of polythiophenes (electrically conductive polymers). Di (2-ethylhexyl) thiodiglycolate is used as a plasticizer in rubber production ( Vulkanol 90 ).

Medical importance

In the event of poisoning with vinyl chloride or treatment with ifosfamide , thiodiglycolic acid can be detected and quantified in the urine.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on thiodi (acetic acid) in the GESTIS substance database of the IFA , accessed on March 27, 2013(JavaScript required) .
↑ ^a ^b ^c ^d Entry on thiodiglycolic acid in the Hazardous Substances Data Bank , accessed on March 27, 2013.
↑ Data sheet 2,2′-thiodiacetic acid (PDF) from Merck , accessed on March 27, 2013.
↑ bruno bock: thiodiglycolic , accessed on September 4 2016th
↑ Theresa M. Visarius, Heinz Bähler, Adrian Küpfer, Thomas Cerny, H. Bernhard Lauterburg: Thiodiglycolic acid is excreted by humans receiving ifosfamide and Inhibits mitochondrial function in rats . In: Drug Metabolism and Disposition . tape 26 , no. 3 , 1998, p. 193-196 , PMID 9492379 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on thiodi (acetic acid) in the GESTIS substance database of the IFA , accessed on March 27, 2013(JavaScript required) .

[hsdb-2] Entry on thiodiglycolic acid in the Hazardous Substances Data Bank , accessed on March 27, 2013.

[Merck-3] Data sheet 2,2′-thiodiacetic acid (PDF) from Merck , accessed on March 27, 2013.

[4] runo bock: thiodiglycolic , accessed on September 4 2016th

[5] Theresa M. Visarius, Heinz Bähler, Adrian Küpfer, Thomas Cerny, H. Bernhard Lauterburg: Thiodiglycolic acid is excreted by humans receiving ifosfamide and Inhibits mitochondrial function in rats . In: Drug Metabolism and Disposition . tape 26 , no. 3 , 1998, p. 193-196 , PMID 9492379 ( PDF ).