2-Mercaptoethanol

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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):
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

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.

References

  1. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a26_767

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