Difference between revisions of "Tert-Butyl chloride"
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| Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
− | | Reference = <ref name="CHRIP">{{ | + | | Reference = <ref name="CHRIP">{{CHRIP|accessdate = 2009-08-22}}.</ref> |
| Formula = C<sub>4</sub>H<sub>9</sub>Cl | | Formula = C<sub>4</sub>H<sub>9</sub>Cl | ||
| MolarMass = 92.567 g/mol | | MolarMass = 92.567 g/mol | ||
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| Solubility = 0.29 g/100 ml (15 ºC) | | Solubility = 0.29 g/100 ml (15 ºC) | ||
| Solubility1 = miscible | | Solubility1 = miscible | ||
− | | Solvent1 = | + | | Solvent1 = ethanol |
| Solubility2 = miscible | | Solubility2 = miscible | ||
− | | Solvent2 = | + | | Solvent2 = diethyl ether |
| VaporPressure = 34.9 kPa (20 °C) | | VaporPressure = 34.9 kPa (20 °C) | ||
| HenryConstant = 0.0128 atm m<sup>3</sup>/mol (est.) | | HenryConstant = 0.0128 atm m<sup>3</sup>/mol (est.) | ||
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== External links == | == External links == | ||
− | * | + | *{{Biodegradability JP|id=1653|name=2-chloro-2-methylpropane|date=2003-01-17}} |
− | * | + | *{{IRIS|id=0417|name=t-Butylchloride}} |
− | * [http://wwwchem.uwimona.edu.jm:1104/lab_manuals/c10expt20.html Preparation 2-chloro-2-methylpropane] | + | * [http://wwwchem.uwimona.edu.jm:1104/lab_manuals/c10expt20.html Preparation of 2-chloro-2-methylpropane] |
* [http://www.cerlabs.com/experiments/10875407331.pdf http://www.cerlabs.com/experiments/10875407331.pdf] | * [http://www.cerlabs.com/experiments/10875407331.pdf http://www.cerlabs.com/experiments/10875407331.pdf] | ||
Latest revision as of 18:03, 24 August 2009
tert-Butyl chloride | |
---|---|
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.
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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