1,2-ethanedithiol

Structural formula
General
Surname	1,2-ethanedithiol
other names	Ethane-1,2-dithiol Dithioglycol 1,2-dimercaptoethane
Molecular formula	C 2 H 6 S 2
Brief description	colorless liquid with an unpleasant odor
External identifiers / databases
CAS number 540-63-6 EC number 208-752-3 ECHA InfoCard 100,007,958 PubChem 10902 Wikidata Q2738870
properties
Molar mass	94.20 g mol −1
Physical state	liquid
density	1.12 g cm −3
Melting point	−41 ° C
boiling point	146-149 ° C
Vapor pressure	5.3 mbar (23 ° C)
solubility	practically insoluble in water
Refractive index	1.558 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-301-310-330 P: 210-271-280-309 + 310-304 + 340-302 + 352
Toxicological data	342 mg kg −1 ( LD 50 ,  mouse ,  oral )
Thermodynamic properties
ΔH f 0	−54.3 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

1,2-ethanedithiol is a chemical compound from the group of thiols .

Extraction and presentation

1,2-Ethanedithiol is produced industrially by the reaction of 1,2-dichloroethane with sodium hydrogen sulfide . In the laboratory, it can also be represented by reacting 1,2-dibromoethane with thiourea , followed by hydrolysis .

properties

1,2-Ethanedithiol is a slightly volatile, colorless liquid with an unpleasant odor, which is practically insoluble in water.

use

1,2-Ethanedithiol is used to produce cyclic thioacetals from aldehydes . In the solid phase synthesis of peptides using the Fmoc strategy , when sensitive amino acids such as cysteine and methionine are present , some 1,2-ethanedithiol is often added to suppress side reactions when the trifluoroacetic acid is deprotected .

safety instructions

The vapors of 1,2-ethanedithiol can form an explosive mixture with air ( flash point 50 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i j k} Entry on 1,2-ethanedithiol in the GESTIS substance database of the IFA , accessed on June 19, 2013(JavaScript required) .
2. ↑ Data sheet 1,2-ethanedithiol from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
3. ^ SD Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects: D. Vol . 3 . Royal Society of Chemistry, 1999, ISBN 0-85404-818-9 , pp. 88 ( limited preview in Google Book search).
4. ↑ 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. 5-23.
5. ↑ Speziale, AJ: Ethanedithiol In: Organic Syntheses . 30, 1950, p. 35, doi : 10.15227 / orgsyn.030.0035 ; Coll. Vol. 4, 1963, p. 401 ( PDF ).
6. ↑ Adalbert Wollrab: Organic Chemistry: An Introduction for Teaching and Minor Students . Springer DE, 2009, ISBN 3-642-00781-3 , p. 1084 ( limited preview in Google Book search).
7. ↑ DS King, CG Fields, GB Fields: A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis. In: International journal of peptide and protein research. Volume 36, Number 3, September 1990, pp. 255-266, PMID 2279849 .
8. ^ H. Huang, DL Rabenstein: A cleavage cocktail for methionine-containing peptides. In: The journal of peptide research: official journal of the American Peptide Society. Volume 53, Number 5, May 1999, pp. 548-553, PMID 10424350 .
9. ↑ E. Bianchi, G. del Giudice et al. a .: Synthetic peptides for Plasmodium vivax malaria sero-epidemiology. Application of Fmoc-polyamide and displacement chromatography. In: International journal of peptide and protein research. Volume 37, Number 1, January 1991, pp. 7-13, PMID 1710611 .