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2-Chloro-2-methylpropane

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2-Chloro-2-methylpropane Basic information

Product Name:
2-Chloro-2-methylpropane
Synonyms:
  • 2-CHLORO-2-METHYLPROPANE,REAGENT
  • 2-Chloro-2-methylpropane, 98+%
  • tert-Butylchloride,98+%
  • 1-Chloro-1,1-dimethylethane
  • 2-Chlor-2-methylpropan
  • 2-chloro-2-methyl-propan
  • 2-Methyl-2-propyl chloride
  • 2-methyl-2-propylchloride
CAS:
507-20-0
MF:
C4H9Cl
MW:
92.57
EINECS:
208-066-4
Product Categories:
  • API Intermediate
  • Organics
  • CHLORO ALKANE COMPOUNDS
Mol File:
507-20-0.mol
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2-Chloro-2-methylpropane Chemical Properties

Melting point:
-25 °C (lit.)
Boiling point:
51-52 °C (lit.)
Density 
0.851 g/mL at 25 °C (lit.)
vapor density 
3.2 (vs air)
vapor pressure 
4.82 psi ( 20 °C)
refractive index 
n20/D 1.385(lit.)
Flash point:
−10 °F
storage temp. 
Store at <= 20°C.
solubility 
soluble in Chloroform
form 
Liquid
color 
Clear
explosive limit
1.8-10.1%(V)
Water Solubility 
SLIGHTLY SOLUBLE
Merck 
14,1562
BRN 
1730872
Dielectric constant
10.949999999999999
Stability:
Stable. Extremely flammable. Note low flash point. Incompatible with strong oxidizing agents. Vapour, being much denser than air, may travel considerable distances to a source of ignition. Hygroscopic.
InChIKey
NBRKLOOSMBRFMH-UHFFFAOYSA-N
LogP
2.45 at 20-25℃
CAS DataBase Reference
507-20-0(CAS DataBase Reference)
NIST Chemistry Reference
Propane, 2-chloro-2-methyl-(507-20-0)
EPA Substance Registry System
tert-Butyl chloride (507-20-0)
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Safety Information

Hazard Codes 
F
Risk Statements 
11
Safety Statements 
16-29-33-7/9-9
RIDADR 
UN 1127 3/PG 2
WGK Germany 
1
RTECS 
TX5040000
Autoignition Temperature
570°C
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29031980

MSDS

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2-Chloro-2-methylpropane Usage And Synthesis

Chemical Properties

tert-Butyl chloride is a colourless liquid. Miscible with alcohol and ether, insoluble in water. It is flammable and releases toxic phosgene when heated. Reacts violently with oxidizing agents. More toxic than 1-chlorobutane. tert-Butyl Chloride has a wide range of applications in the fields of medicine, pesticides, rubber, plastic additives and other chemical industries.

Uses

2-Chloro-2-methylpropane is an alkylating agent that is used to functionalize molecules with tert-butyl group.
It serves as an effective chlorinating agent, in combination with the ionic liquid, 1-butyl-3-methylimidazolium bromide for converting alcohols into chlorides.
It can also be used to prepare tert-butyl ethers by treating with corresponding alcohols.

Application

tert-Butyl chloride plays an important role as a starting material to perform nucleophilic substitution reactions in order to prepare alcohol and alkoxides salts. It is used as an alkylating agent for the introduction of tert-butyl group and is also involved in Friedel-Crafts reactions. It is employed as an intermediate for the synthesis of agrochemicals and pharmaceuticals.

Flammability and Explosibility

Flammable

Safety Profile

Questionable carcinogen with experimental neoplastigenic data. Dangerous fire hazard when exposed to heat, flame (sparks), and oxidlzers. To fight fue, use water, spray, fog, alcohol foam, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, ALIPHATIC.

Synthesis

tert-Butyl chloride is prepared from tertbutyl alcohol (tert-butanol) using an acid catalyzed dehydration reaction.

The first step of the overall reaction is an acid-base reaction between the t-butanol and the hydrochloric acid. The t-butanol is a weak base and the hydrochloric acid is a strong acid. The alcoholic oxygen becomes fully protonated and so the equilibrium lies far to the right. In the second step we have the slow loss of water to form a carbocation intermediate. This species is very reactive and is immediately attacked by the chloride ion liberated in the first step to form tert-Butyl chloride.

Purification Methods

Purification methods commonly used for other alkyl halides lead to decomposition. Some impurities can be removed by photochlorination with a small amount of chlorine prior to use. The liquid is washed with ice water, dried with CaCl2 or CaCl2 + CaO and fractionally distilled. It has been further purified by repeated fractional crystallisation by partial freezing. [Beilstein 1 IV 288.]

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