Difference between revisions of "Tert-Butyl chloride"

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{{lowercase title}}
 
{{chembox
 
{{chembox
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| Name = ''tert''-Butyl chloride
 
| ImageFileL1 = Tert-butyl-chloride-2D-skeletal.png
 
| ImageFileL1 = Tert-butyl-chloride-2D-skeletal.png
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| ImageSizeL1 = 100px
+
|   ImageSizeL1 = 100px
 
| ImageFileR1 = Tert-butyl-chloride-3D-balls.png
 
| ImageFileR1 = Tert-butyl-chloride-3D-balls.png
−
| ImageSizeR1 = 120px
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|   ImageSizeR1 = 120px
 
| IUPACName = 2-chloro-2-methylpropane
 
| IUPACName = 2-chloro-2-methylpropane
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| OtherNames = 1,1-dimethylethyl chloride<br>1-chloro-1,1-dimethylethane<br>2-chloroisobutane<br>2-methyl-2-chloropropane<br>chlorotrimethylmethane<br>trimethylchloromethane<br>t-butyl chloride<br>tert-butyl chloride<br>t-BuCl<br>UN 1127
+
|   OtherNames = 1,1-dimethylethyl chloride<br/>1-chloro-1,1-dimethylethane<br/>chlorotrimethylmethane<br/>trimethylchloromethane<br/>''t''-butyl chloride
 
| Section1 = {{Chembox Identifiers
 
| Section1 = {{Chembox Identifiers
 +
|  InChI = 1/C4H9Cl/c1-4(2,3)5/h1-3H3
 +
|  StdInChI = 1S/C4H9Cl/c1-4(2,3)5/h1-3H3
 +
|  InChIKey = NBRKLOOSMBRFMH-UHFFFAOYAL
 +
|  StdInChIKey = NBRKLOOSMBRFMH-UHFFFAOYSA-N
 
|  CASNo = 507-20-0
 
|  CASNo = 507-20-0
−
|  EINECS = 208-066-4
+
|    CASNo_Ref = {{cascite}}
 +
|  EC-number = 208-066-4
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|  ChemSpiderID = 10054
 
|  PubChem = 10486
 
|  PubChem = 10486
 
|  SMILES = CC(C)(C)Cl
 
|  SMILES = CC(C)(C)Cl
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|  InChI = 1/C4H9Cl/c1-4(2,3)5/h1-3H3
 
 
|  RTECS = TX5040000
 
|  RTECS = TX5040000
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|  UN-number = 1127
 
   }}
 
   }}
 
| Section2 = {{Chembox Properties
 
| Section2 = {{Chembox Properties
 +
|  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
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|  MolarMass = 92.57 g/mol
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|  MolarMass = 92.567 g/mol
 
|  Appearance = Colorless liquid
 
|  Appearance = Colorless liquid
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|  Density = 0.84 g cm<sup>−3</sup>
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|  Density = 0.847 g/cm<sup>3</sup> (15 ºC)
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|  MeltingPt = −26 °C
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|  MeltingPt = −26.5 °C
 
|  BoilingPt = 51 °C
 
|  BoilingPt = 51 °C
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|  Solubility = Sparingly sol in water, miscible with alcohol and ether
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|  Solubility = 0.29 g/100 ml (15 ºC)
 +
|  Solubility1 = miscible
 +
|    Solvent1 = ethanol
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|  Solubility2 = miscible
 +
|    Solvent2 = diethyl ether
 
|  VaporPressure = 34.9 kPa (20 °C)
 
|  VaporPressure = 34.9 kPa (20 °C)
 +
|  HenryConstant = 0.0128 atm&thinsp;m<sup>3</sup>/mol (est.)
 +
|  LogP = 2.45 (est.)
 
   }}
 
   }}
−
| Section3 = {{Chembox Hazards
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| Section7 = {{Chembox Hazards
−
|  EUClass = Flammable ('''F''')
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|  Reference = <ref name="CHRIP"/><ref>{{GHS class NZ|id=15657|accessdate=2009-08-22}}.</ref>
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|   MainHazards =
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|  EUIndex = not listed
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|   FlashPt = −9 °C (open cup)<br>−23 °C (closed cup)
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|  ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/CH/2-chloro-2-methylpropane.html External MSDS]
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|  Autoignition = 540 °C
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|  GHSPictograms = {{GHS flame|Flam. Liq. 2}}
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|  NFPA-H = 2
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|  GHSSignalWord = DANGER
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|  NFPA-F = 3
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|  HPhrases = {{H-phrases|225}}
−
|   NFPA-R = 0
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|  PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}
−
|  NFPA-O =
+
|  FlashPt = 0 °C (32 ºF)
−
|  RPhrases = {{R12}}, {{R36/37/38}}
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|  Autoignition = 540 °C (1004 ºF)
−
|  SPhrases = {{S7}}, {{S9}}, {{S16}}, {{S29}}, {{S33}}
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|  ExploLimits = 1.8–10.1%
 
   }}
 
   }}
 
}}
 
}}
  
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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 [[solvation|dissolved]] into it. The compound is [[flammable]] and [[Volatile organic compound|volatile]], and its main use is as a starting molecule to carry out [[nucleophilic substitution|nucleophilic substitution reactions]], to produce different substances, ranging from [[alcohols]] to [[alkoxide]] [[salts]].
+
'''''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 [[solvation|dissolved]] into it. The compound is [[flammable]] and volatile, and its main use is as a starting molecule to carry out [[nucleophilic substitution|nucleophilic substitution reactions]], to produce different substances, ranging from [[alcohols]] to [[alkoxide]] salts.
  
−
When tert-butyl chloride is dissolved in water, a [[chemical polarity|polar]] and [[protic solvent]], the bulky [[chloride]] [[substituent]] is carried away by it, and isolated from the [[aliphatic compound|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.
+
When ''tert''-butyl chloride is dissolved in water, a [[chemical polarity|polar]] and [[protic solvent]], the bulky [[chloride]] [[substituent]] is carried away by it, and isolated from the [[aliphatic compound|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==
 
==Synthesis==
Line 57: Line 72:
 
[[Image:0-SN1-tBuOH-to-tBuCl-2D-skeletal.png|250px]]
 
[[Image:0-SN1-tBuOH-to-tBuCl-2D-skeletal.png|250px]]
  
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Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the Step 2 allows the [[SN1|S<sub>N</sub>1]] mechanism to be followed, whereas a primary alcohol would follow an [[SN2|S<sub>N</sub>2]] mechanism.
+
Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the step&nbsp;2 allows the [[SN1|S<sub>N</sub>1]] mechanism to be followed, whereas a primary alcohol would follow an [[SN2|S<sub>N</sub>2]] mechanism.
  
 
== See also ==
 
== See also ==
 
* [[Isobutane]]
 
* [[Isobutane]]
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 +
==References==
 +
{{reflist}}
  
 
== External links ==
 
== External links ==
−
* [http://physchem.ox.ac.uk/MSDS/CH/2-chloro-2-methylpropane.html Safety MSDS data]
+
*{{Biodegradability JP|id=1653|name=2-chloro-2-methylpropane|date=2003-01-17}}
−
* [http://wwwchem.uwimona.edu.jm:1104/lab_manuals/c10expt20.html Preparation 2-chloro-2-methylpropane]
+
*{{IRIS|id=0417|name=t-Butylchloride}}
 +
* [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 17:03, 24 August 2009

tert-Butyl chloride
Tert-butyl-chloride-2D-skeletal.png
Tert-butyl-chloride-3D-balls.png
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 [507-20-0]
EC number 208-066-4
UN number 1127
RTECS TX5040000
ChemSpider 10054
PubChem 10486
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 Flam. Liq. 2
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.

Step 1
Step 2
Step 3
1-HCl-protonates-tBuOH-2D-skeletal.png
2-water-leaves-protonated-tBuOH-2D-skeletal.png
3-chloride-attacks-tBu-cation-2D-skeletal.png
The acid protonates the alcohol, forming a good leaving group (water).
Water leaves the protonated t-BuOH, forming a relatively stable tertiary carbocation.
The chloride ion attacks the carbocation, forming t-BuCl.

The overall reaction, therefore, is:

0-SN1-tBuOH-to-tBuCl-2D-skeletal.png

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. ↑ 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).
  2. ↑ 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

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