Sodium ethanethiolate

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.

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

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