2-Chloro-2-methylpropane

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+%;2-Chlor-2-methylpropan;2-chloro-2-methyl-propan;2-Methyl-2-propyl chloride;butyl chloride 2-chloro-2-methyl propane;2-Chloro-2-methylpropane,99%
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
2-Chloro-2-methylpropane Structure
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.)
Fp −10 °F
storage temp. Store at <= 20°C.
solubility soluble in Chloroform
form Liquid
color Clear
explosive limit1.8-10.1%(V)
Water Solubility SLIGHTLY SOLUBLE
Merck 14,1562
BRN 1730872
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.
InChIKeyNBRKLOOSMBRFMH-UHFFFAOYSA-N
LogP2.45 at 20-25℃
CAS DataBase Reference507-20-0(CAS DataBase Reference)
NIST Chemistry ReferencePropane, 2-chloro-2-methyl-(507-20-0)
EPA Substance Registry Systemtert-Butyl chloride (507-20-0)
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 Temperature570°C
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29031980
MSDS Information
ProviderLanguage
tert-Butyl chloride English
SigmaAldrich English
ACROS English
ALFA English
2-Chloro-2-methylpropane Usage And Synthesis
Chemical Propertiestert-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.
Uses2-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.
Applicationtert-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 ExplosibilityFlammable
Safety ProfileQuestionable 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.
Synthesistert-Butyl chloride is prepared from tertbutyl alcohol (tert-butanol) using an acid catalyzed dehydration reaction.
Preparation of t-Butyl Chloride
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 MethodsPurification 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.]
Methyl t-butyl chloroformate tert-BUTYL CHLORIDE extrapure Propane p-Aminobenzylchloride Di(trimethylol propane) 1-bromo-2-chloro-2-methylpropane DI-TERT-BUTYLDICHLOROSILANE Cinnamyl chloride 1-BROMO-3-CHLORO-2-METHYLPROPANE,3-bromo-1-chloro-2-methylpropan 2-CHLORO-2-METHYLPROPANE, [2-14C] BUTYL OLEATE 1,2-dibromo-3-chloro-2-methylpropane 1,2-Dibromo-1-chloro-2-methylpropane Neophyl chloride 3-chloro-2-methylpropane-1,2-diol tert-BUTYL CHLORIDE FOR SYNTHESIS 2-CHLORO-2-METHYLPROPANE-D9,TERT-BUTYL CHLORIDE (D9),2-CHLORO-2-METHYLPROPANE-D9, 99 ATOM % D

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