Sodium ethanethiolate

Sodium ethanethiolate

Names
Other names Sodium thioethoxide Sodium ethyl mercaptide Sodium ethylmercaptide
Identifiers
CAS Number	684-910-9
PubChem CID	4459711
Properties
Chemical formula	C2H5NaS
Molar mass	84.11 g·mol−1
Appearance	white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sodium ethanethiolate is an organosulfur compound with the formula CH₃CH₂SNa. It is the sodium salt of the conjugate base of ethanethiol. This compound is commercially available as a white solid that is soluble in polar organic solvents. Sodium ethanethiolate is a reagent in organic synthesis. Hydrolysis of sodium ethanethiolate, e.g. in humid air, produces ethanethiol, which has a low odor threshold and a noxious "rotten egg" smell.

Preparation

Sodium ethanethiolate can be produced by treating a solution of ethanethiol with sodium hydride: ^[1]

CH₃CH₂SH + NaH → CH₃CH₂SNa + H₂

The closely related sodium methanethiolate can be prepared and used in situ (i.e., without isolation) by treatment of a solution of methanethiol with strong base such as sodium hydroxide. ^{[2] [3]}

Reactions

Sodium ethanethiolate is a source of ethanethiolate, a powerful nucleophile. It is used to cleave methoxy-aryl ethers: ^[1]

NaSCH₂CH₃ + Ar−O−CH₃ → Ar−ONa + CH₃CH₂SCH₃ (Ar = aryl)

It converts alkyl halides to ethyl thioethers

NaSCH₂CH₃ + RX → RSCH₂CH₃ + NaX (X = halogen, R = alkyl)

Oxidation of sodium methanethiolate gives diethyldisulfide:

2 NaSCH₂CH₃ + I₂ → CH₃CH₂SSCH₂CH₃ + 2 NaI

References

1. Mirrington, R. N.; Feutrill, G. I. (1873). "Orcinol Monomethyl Ether". Organic Syntheses . 533: 90. doi:10.15227/orgsyn.053.0090 .
2. Bruce W. Erickson (1974). "γ-Hydroxy-α,β-unsaturated Aldehydes via 1,3-Bis(methylthio)allyllithium: trans-4-Hydroxy-2-hexenal". Organic Syntheses. 54: 19. doi:10.15227/orgsyn.054.0019.
3. Cogolli, P.; Maiolo, F.; Testaferri, L.; Tingoli, M.; Tiecco, M. (1979). "Nucleophilic Aromatic substitution reactions of unactivated aryl halides with thiolate ions in hexamethylphosphoramide". J. Org. Chem. 44: 2462. doi:10.1021/jo01329a011.