Sodium methanethiolate
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| Names | |
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| Preferred IUPAC name
Sodium methanethiolate | |
| Other names
sodium thiomethoxide, sodium methyl mercaptide, sodium thiomethylate, methanethiol sodium salt, methyl mercaptan sodium salt, MeSNa
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.023.609 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| CH3NaS | |
| Molar mass | 70.08 g·mol−1 |
| Appearance | white[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.
Preparation
[edit]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
[edit]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]
Oxidation of sodium methanethiolate gives dimethyldisulfide:
- 2 NaSCH3 + I2 → CH3SSCH3 + 2 NaI
References
[edit]- ^ a b c d 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.
- ^ 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.
- ^ 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.
- ^ 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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