tert-Butyl chloride
| tert-Butyl chloride | |
|---|---|
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| IUPAC name | 2-chloro-2-methylpropane |
| Other names | 1,1-dimethylethyl chloride 1-chloro-1,1-dimethylethane chlorotrimethylmethane trimethylchloromethane t-butyl chloride |
| Identifiers | |
| InChI | InChI=1/C4H9Cl/c1-4(2,3)5/h1-3H3 |
| InChIKey | NBRKLOOSMBRFMH-UHFFFAOYAL |
| Standard InChI | InChI=1S/C4H9Cl/c1-4(2,3)5/h1-3H3 |
| Standard InChIKey | NBRKLOOSMBRFMH-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| UN number | 1127 |
| RTECS | TX5040000 |
| ChemSpider | |
| PubChem | |
| SMILES | |
| Properties[1] | |
| Chemical formula | C4H9Cl |
| Molar mass | 92.567 g/mol |
| Appearance | Colorless liquid |
| Density | 0.847 g/cm3 (15 ºC) |
| Melting point |
−26.5 °C |
| Boiling point |
51 °C |
| Solubility in water | 0.29 g/100 ml (15 ºC) |
| Solubility in ethanol | miscible |
| Solubility in diethyl ether | miscible |
| log P | 2.45 (est.) |
| Vapor pressure | 34.9 kPa (20 °C) |
| kH | 0.0128 atm m3/mol (est.) |
| Hazards[1][2] | |
| Material safety data sheet (MSDS) | External MSDS |
| EU index number | not listed |
| GHS pictograms | 
|
| GHS signal word | DANGER |
| GHS hazard statements | H225 |
| GHS precautionary statements | P210, P233, P240, P241, P242, P243, P280, P303+361+353, P370+378, P403+235, P501 |
| Flash point | 0 °C (32 ºF) |
| Autoignition temp. | 540 °C (1004 ºF) |
| Explosive limits | 1.8–10.1% |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
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.
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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.
See also
References
- ↑ 1.0 1.1 Chemical Risk Information Platform (CHRIP), <http://www.safe.nite.go.jp/english/db.html> (accessed 22 August 2009), National Institute of Technology and Evaluation (Japan).
- ↑ HSNO Chemical Classification Information Database, <http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=15657> (accessed 22 August 2009), New Zealand Environmental Risk Management Authority.
External links
- Biodegradation and Bioconcentration of 2-chloro-2-methylpropane from the National Institute of Technology and Evaluation (Japan)
- U.S. Environmental Protection Agency Integrated Risk Information System entry for "t-Butylchloride"
- Preparation of 2-chloro-2-methylpropane
- http://www.cerlabs.com/experiments/10875407331.pdf
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