Sodium methanethiolate

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Sodium methanethiolate
Sodium methanethiolate.svg
Names
Preferred IUPAC name
Sodium methanethiolate
Other names
sodium thiomethoxide, sodium methyl mercaptide, sodium thiomethylate, methanethiol sodium salt, methyl mercaptan sodium salt, MeSNa
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.023.609 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 225-969-9
PubChem CID
UNII
  • InChI=1S/CH4S.Na/c1-2;/h2H,1H3;/q;+1/p-1 Yes check.svgY
    Key: RMBAVIFYHOYIFM-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/CH4S.Na/c1-2;/h2H,1H3;/q;+1/p-1
  • [Na+].[S-]C
Properties
CH3NaS
Molar mass 70.08 g·mol−1
Appearancewhite [1]
Density 1.43 g/cm3 [2]
Melting point 88–90 °C (190–194 °F; 361–363 K)
soluble [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sodium methanethiolate or sodium thiomethoxide is an organosulfur compound with the formula CH3SNa. It is the sodium salt of the conjugate base of methanethiol. This compound is commercially available as a white solid that is soluble in polar organic solvents. Sodium methanethiolate is a reagent in organic synthesis [1] and a byproduct of some industrial processes. Hydrolysis of sodium methanethiolate, e.g. in humid air, produces methanethiol, which has a low odor threshold and a noxious "rotten egg" smell.

Contents

Preparation

Sodium methanethiolate can be produced by treating a solution of methanethiol in an etherial solvent with sodium hydride:

CH3SH + NaH → CH3SNa + H2

It is also prepared and used in situ (i.e., without isolation) by treatment of a solution of methanethiol with strong base such as sodium hydroxide. [3] [4]

Reactions

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

NaSCH3 + Ar−O−CH3 → Ar−ONa + CH3SCH3 (Ar = aryl)

It converts alkyl halides to methyl thioethers: [5]

NaSCH3 + RX → RSCH3 + NaX (X = halogen, R = alkyl)

Oxidation of sodium methanethiolate gives dimethyldisulfide:

2 NaSCH3 + I2 → CH3SSCH3 + 2 NaI

References

  1. 1 2 3 4 Chakraborty, Pradip (2014). "Sodium Methanethiolate". Encyclopedia of Reagents for Organic Synthesis. pp. 1–5. doi:10.1002/047084289X.rn01716. ISBN   978-0-470-84289-8.
  2. ↑ Weiss, Erwin; Joergens, Uwe (1972). "Die Kristallstrukturen der Alkalimethylmercaptide CH 3 SM (M = Li, Na, K)". Chemische Berichte. 105 (2): 481–486. doi:10.1002/cber.19721050214.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ P. G. Gassman; T. J. van Bergen (1977). "Indoles from Anilines: Ethyl 2-Methylindole-5-Carboxylate". Organic Syntheses. 56: 72. doi:10.15227/orgsyn.056.0072.
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