tert-Butyl chloride
| tert-Butyl chloride | |
|---|---|
| 2-chloro-2-methylpropane | |
| Other names 1,1-dimethylethyl chloride 1-chloro-1,1-dimethylethane chlorotrimethylmethane trimethylchloromethane t-butyl chloride | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 507-20-0 
|
| PubChem | 10486 |
| ChemSpider | 10054 |
| EC-number | 208-066-4 |
| UN number | 1127 |
| RTECS number | TX5040000 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C4H9Cl |
| Molar mass | 92.57 g/mol |
| Appearance | Colorless liquid |
| Density | 0.84 g cm−3 |
| Melting point |
−26 °C, 247 K, -15 °F |
| Boiling point |
51 °C, 324 K, 124 °F |
| Solubility in water | Sparingly sol in water, miscible with alcohol and ether |
| Vapor pressure | 34.9 kPa (20 °C) |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| EU classification | Flammable (F) |
| R-phrases | R12, R36/37/38 |
| S-phrases | S7, S9, S16, S29, S33 |
| NFPA 704 | |
| Flash point | −9 °C (open cup) −23 °C (closed cup) |
| Autoignition temperature |
540 °C |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
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 heterolytic 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.
Synthesis
tert-Butyl chloride can be synthesized in the laboratory by the SN1 reaction of tert-Butanol with concentrated hydrochloric acid, as shown below.
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.
