Tert-Butyl chloride
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| Tert-Butyl chloride | |
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| IUPAC name | 2-chloro-2-methylpropane |
| Other names | 1,1-dimethylethyl chloride 1-chloro-1,1-dimethylethane 2-chloroisobutane 2-methyl-2-chloropropane chlorotrimethylmethane trimethylchloromethane t-butyl chloride tert-butyl chloride t-BuCl UN 1127 |
| Identifiers | |
| CAS number | [507-20-0] |
| PubChem | |
| EINECS number | |
| RTECS number | TX5040000 |
| SMILES | CC(C)(C)Cl |
| InChI | 1/C4H9Cl/c1-4(2,3)5/h1-3H3 |
| Properties | |
| Molecular formula | C4H9Cl |
| Molar mass | 92.57 g/mol |
| Appearance | Colorless liquid |
| Density | 0.89 g cm−3 |
| Melting point |
−26 °C |
| Boiling point |
51 °C |
| Vapor pressure | 34.9 kPa (20 °C) |
| Hazards | |
| EU classification | Flammable (F) |
| NFPA 704 |
 3
2
0
|
| R-phrases | R12, R36/37/38 |
| S-phrases | S7, S9, S16, S29, S33 |
| Flash point | −9 °C (open cup) −23 °C (closed cup) |
| Autoignition temperature |
540 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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tert-Butyl chloride is a colorless, liquid organic compound at room temperature. It is sparingly soluble in water, with a tendency to undergo spontaneous solvolysis when dissolved into it. The compound is flammable and volatile, and its main use is as a starting molecule to carry out nucleophilic substitution reactions, to produce different substances, ranging from alcohols to alkoxide salts.
When tert-butyl chloride is dissolved in water, a polar and protic solvent, the bulky chloride substituent is carried away by it, and isolated from the aliphatic chain, causing an heterolitic rupture of the compound, giving rise to a carbocation which eventually becomes a tertiary alcohol after a water molecule reacts with it, releasing hydrochloric acid as the final product. If a different, stronger nucleophilic agent is present at the moment of reaction, reaction product may not be an alcohol, but a tertiary carbon with the nucleophile as a substituent.
[edit] Synthesis
tert-Butyl chloride can be synthesized in the laboratory by the SN1 reaction of tert-Butanol with concentrated hydrochloric acid, as shown below.
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The overall reaction, therefore, is:
Because tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the Step 2 allows the SN1 mechanism to be followed, whereas a primary alcohol would follow an SN2 mechanism.
