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60-24-2 - 2-Mercaptoethanol, 98+% - Thioethylene glycol - Thioglycol - A15890 - Alfa Aesar

A15890 2-Mercaptoethanol, 98+%

CAS Number
60-24-2
Synonyms
Thioethylene glycol
Thioglycol

Size Price ($) Quantity Availability
250g 26.06
1000g 70.86
5000g 256.50
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2-Mercaptoethanol, 98+%

MDL
MFCD00004890
EINECS
200-464-6

Chemical Properties

Formula
HSCH2CH2OH
Formula Weight
78.13
Melting point
-100°
Boiling Point
156-158°
Flash Point
73°(163°F)
Density
1.114
Refractive Index
1.500
Sensitivity
Air Sensitive & Hygroscopic
Solubility
Miscible with water, alcohol, ether, benzene and other organic solvents.

Applications

Solubilizes proteins by reducing disulfide linkages2-Mercaptoethanol is used in the preparation of nano-graphene for cellular imaging and drug delivery as well as multifunctional polymeric micelle. It acts as a reducing agent used in electrophoresis, amino acid detection, and distinguishing ssDNA/dsDNA. It is also employed as a standard buffer. It is also used in the preparation of PVC heat stabilizers and as a chain transfer agent in the manufacture of PVC. Further, it is used in some RNA isolation procedures to eliminate ribonuclease. It is utilized as a corrosion inhibitor and ore floatation agent. In biochemistry, it is useful to study the activity of the immune system.

Notes

Hygroscopic. Air sensitive and heat sensitive. Incompatible with metals, strong acids, heavy metal salts and oxidizing agents. Store in a cool place.

Literature References

Protective agent for preventing oxidation of thiol groups in proteins: Enzyme Assays, R. Eisenthal and M. J. Danson, Eds., OUP, Oxford (1992), p 265.

In the presence of BF3 etherate, reacts with carbonyl compounds to give monothioacetals (1,3-oxathiolanes): J. Org. Chem., 33, 2133 (1968). Amberlyst 15 is also effective: Synthesis, 1826 (2001), as is In(OTf)3: Synlett, 1535 (2002). 1,3-Oxathiolanes can be prepared from acid-sensitive aldehydes with LiBH4 as catalyst in acetonitrile: Synlett, 238 (2001). Cleavage can be effected, e.g. with chloramine-T: Tetrahedron Lett., 3445 (1971), isoamyl nitrite: Tetrahedron. Lett., 3561 (1978), or periodic acid: Tetrahedron Lett., 37, 4331 (1996). Selective cleavage of oxathiolanes in the presence of dithiolanes has been achieved with triphenylcarbenium tetrafluoroborate: J. Chem. Soc., Perkin 1, 542 (1972), or 4-nitrobenzaldehyde catalyzed by TMS-OTf: J. Chem. Soc. Chem. Commun., 1937 (1994). Compare 1,2-Ethanedithiol, L12865.

2-Mercaptoethanol is a reagent for the specific cleavage of the N-dithiasuccinimide protecting group from amines. See Chlorocarbonyl­sulfenyl­ chloride, L06432.

Sugimoto, Y.; Kitazumi, Y.; Shirai, O.; Yamamoto, M.; Kano, K. Role of 2-mercaptoethanol in direct electron transfer-type bioelectrocatalysis of fructose dehydrogenase at Au electrodes. Electrochim. Acta 2015, 170, 242-247.

Mohebbi, S.; Eslami, S. Electrocatalytic oxidation of 2-mercaptoethanol using modified glassy carbon electrode by MWCNT in combination with unsymmetrical manganese(II) Schiff base complexes. Mater. Res. Bull. 2015, 66, 219-225.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H310-H315-H317-H335-H318-H400-H410-H227

Toxic if swallowed. Fatal in contact with skin. Causes skin irritation. May cause an allergic skin reaction. May cause respiratory irritation. Causes serious eye damage. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects. Combustible liquid.

Precautionary Statements: P210-P261-P262-P273-P301+P310-P305+P351+P338-P361-P302+P350-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Avoid release to the environment. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Remove/Take off immediately all contaminated clothing. IF ON SKIN: Gently wash with plenty of soap and water. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,5869
Beilstein
773648
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
KL5600000

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