Sodium ethanethiolate

Sodium ethanethiolate
Names
	Other names Sodium thioethoxide; Sodium ethyl mercaptide; Sodium ethylmercaptide;
Identifiers
CAS Number	811-51-8;
3D model (JSmol)	Interactive image;
ChemSpider	3658468;
EC Number	684-910-9;
PubChem CID	4459711;
CompTox Dashboard (EPA)	DTXSID001001774 ;
	InChI InChI=1S/C2H6S.Na/c1-2-3;/h3H,2H2,1H3;/q;+1/p-1 Key: QJDUDPQVDAASMV-UHFFFAOYSA-M;
	SMILES CC[S-].[Na+];
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

^ ^a ^b Mirrington, R. N.; Feutrill, G. I. (1873). "Orcinol Monomethyl Ether". Organic Syntheses. 533: 90. doi:10.15227/orgsyn.053.0090.
^ 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.
^ 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 (15): 2462. doi:10.1021/jo01329a011.

[OS-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 (15): 2462. doi:10.1021/jo01329a011.

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