1,2-Ethanedithiol | |
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Ethane-1,2-dithiol |
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Other names
Dimercaptoethane |
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Identifiers | |
CAS number | 540-63-6 |
ChemSpider | 13865015 |
UNII | 92T634FLAR |
RTECS number | KI3325000 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C2H6S2 |
Molar mass | 94.2 g mol−1 |
Appearance | Colorless liquid |
Density | 1.123 g/cm³ |
Melting point |
-41 °C, 232 K, -42 °F |
Boiling point |
146 °C, 419 K, 295 °F (46 mmHg) |
Solubility in water | Slightly sol |
Solubility in other solvents | Good solubility in most organic solvents |
Acidity (pKa) | ~11 |
Refractive index (nD) | 1.5589 (D-line, 25 °C) |
Hazards | |
EU classification | Toxic (T) |
R-phrases | R10 R22 |
S-phrases | S16 |
NFPA 704 |
2
2
0
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Flash point | 50 °C |
Related compounds | |
Related thiols | Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
1,2-Ethanedithiol is a colorless liquid with the formula C2H4(SH)2. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.
1,2-Ethanedithiol is commercially available. It can be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.[1]
This compound is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates. [2]
Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to 1,3-dioxalanes and 1,3-dioxanes. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.