Monosodium acetylide
| Names | |
|---|---|
| IUPAC name
Ethynylsodium | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.012.645 |
| EC Number |
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| 174471 | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C2HNa | |
| Molar mass | 48.020 g·mol−1 |
| Appearance | white solid |
| Density | 1.352 g/cm3 |
| hydrolyzes | |
| Hazards | |
| GHS labelling: | |
| Danger | |
| H261, H314 | |
| P231+P232, P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Monosodium acetylide, also known as sodium hydrogen acetylide, is an organosodium compound with the formula NaC≡CH. It is a sodium salt of acetylene, consisting of sodium cations (Na+) and hydrogen acetylide anions (−C≡CH). It is a derived from acetylene by deprotonation using a sodium base, typically sodium amide.
- HC≡CH + NaNH2 → NaC≡CH + NH3
This compound, a white solid, has been characterized by neutron diffraction, which revealed an Na-C bond and a C≡C bond of 127 pm, which is longer than the C≡C bond length in acetylene itself (120.4 pm).
Monosodium acetylide can be used as a strong nucleophile in organic synthesis. However, it has largely been displaced in this application by monolithium acetylide, which can be prepared more easily.
Monosodium acetylide hydrolizes in contact with water, producing sodium hydroxide and acetylene.
- NaC≡CH + H2O → HC≡CH + NaOH
Monosodium acetylide is used in the Nef synthesis.