2-Mercaptoethanol
| Names | |
|---|---|
| IUPAC name
2-Sulfanylethan-1-ol
| |
| Preferred IUPAC name
2-Sulfanylethan-1-ol | |
| Other names
2-Hydroxy-1-ethanethiol
2-Hydroxyethylmercaptan 2-Mercaptoethan-1-ol Mercaptoethanol Thioethanol Thioethylene glycol β-Mercaptoethanol | |
| Properties | |
| HS-CH2CH2OH C2H6OS | |
| Molar mass | 78.13 g/mol |
| Appearance | Colorless liquid |
| Odor | Disagreeable, sulfurous |
| Density | 1.114 g/cm3 (20 °C) |
| Melting point | −100 °C (−148 °F; 173 K) |
| Boiling point | 157 °C (315 °F; 430 K) |
| Miscible | |
| Solubility | Miscible with alcohols, benzene, esters, ethers, halocarbons, toluene |
| Vapor pressure | 1 mmHg (20 °C) |
| Acidity (pKa) | 9.643 |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 68 °C (154 °F; 341 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
244 mg/Kg (oral, rat) 150 mg/kg (skin, rabbit) |
| Related compounds | |
| Related compounds
|
Thioglycolic acid |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
2-Mercaptoethanol, also called β-mercaptoethanol, is the chemical compound with the formula HS-CH2CH2OH
Contents
Properties
Chemical
Mercaptoethanol reacts with aldehydes and ketones to give the corresponding oxathiolanes.
Some proteins can be denatured by 2-mercaptoethanol, which cleaves the disulfide bonds that may form between thiol groups of cysteine residues.
Physical
Mercaptoethanol is a colorless liquid, with a disagreeable odor, described as "sulfurous" or "fart-like", although it's not as strong as those from other thiol compounds. It is miscible with water and other organic solvents.
Availability
2-Mercaptoethanol is sold by chemical suppliers.
Preparation
2-Mercaptoethanol is produced from the reaction of ethylene oxide with hydrogen sulfide. Thiodiglycol and various zeolites are used to catalyze the reaction.[1]
Projects
- Inhibit protein oxidation
- RNA isolation
Handling
Safety
2-Mercaptoethanol is considered toxic, causing irritation to the nasal passageways and respiratory tract upon inhalation, irritation to the skin, vomiting and stomach pain through ingestion, and potentially death if severe exposure occurs.
Storage
Mercaptoethanol should be kept in airtight bottles, in a closed cabinet, with activated charcoal being used to absorb unpleasant odors.
Disposal
Should be neutralized with dil. hydrogen peroxide or bleach to a less smelly form, then poured down the drain.
