2-chlorobutane

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Structural formula
Structure of 2-chlorobutane
Simplified structural formula without specifying the stereochemistry
General
Surname 2-chlorobutane
other names
  • 2-butyl chloride
  • sec -butyl chloride
  • s -butyl chloride
Molecular formula C 4 H 9 Cl
Brief description

highly volatile, colorless liquid with a characteristic odor

External identifiers / databases
CAS number
  • 78-86-4
  • 22157-31-9 [( R ) -isomer]
  • 22156-91-8 [( S ) -isomer]
EC number 201-151-7
ECHA InfoCard 100.001.047
PubChem 6563
Wikidata Q209347
properties
Molar mass 92.57 g mol −1
Physical state

liquid

density

0.87 g cm −3

Melting point

−140 ° C

boiling point

68 ° C

Vapor pressure

171 h Pa (20 ° C)

solubility
  • poor in water (1 g l −1 at 25 ° C)
  • miscible with ethanol
Refractive index

1.3965 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 05 - Corrosive

danger

H and P phrases H: 225-290-412
P: 210-233-243-273-303 + 361 + 353-403 + 235
Toxicological data

17.5 g kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-chlorobutane is a chemical compound from the group of aliphatic, saturated halogenated hydrocarbons and organic chlorine compounds .

Isomers

2-chlorobutane occurs in two stereoisomeric forms, ( S ) -2-chlorobutane and ( R ) -2-chlorobutane.

Isomers of 2-chlorobutane
Surname ( S ) -2-chlorobutane ( R ) -2-chlorobutane
other names (+) - 2-chlorobutane (-) - 2-chlorobutane
Structural formula Structural formula of (S) -2-Chlorobutane.svg Structural formula of (R) -2-Chlorobutane.svg
CAS number 22156-91-8 22157-31-9
78-86-4 (unspec.)
EC number - -
201-151-7 (unspec.)
ECHA info card - -
100.001.047 (unspec.)
PubChem 637146 23616278
6563 (unspec.)
Wikidata Q27268124 Q27279245
Q209347 (unspec.)

Extraction and presentation

2-Chlorobutane can be produced by reacting 2-butanol and hydrochloric acid (also with zinc chloride ) or by reacting 2-butene with hydrochloric acid.

Synthesis of 2-chlorobutane

A technical synthesis takes place through the thermal chlorination of butane over aluminum oxide at 200 ° C. This produces 1-chlorobutane to the same extent and a small proportion of dichlorobutane. This synthesis is also successful photochemically at 15-20 ° C, the product distribution being similar. Another possibility is the reaction of 2-butanol with hydrogen chloride at 100 ° C.

use

2-chlorobutane is used as an intermediate in the synthesis of fragrances, pesticides, drugs and other chemicals.

safety instructions

The vapors of 2-chlorobutane can form an explosive mixture with air ( flash point approx. −21 ° C, ignition temperature 460 ° C).

Related links

Individual evidence

  1. ↑ a b c d e f g h i j Entry on 2-chlorobutane in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  2. ↑ a b Yixing City Changjili Chemicals: 2-Chlorobutane ( Memento from May 2, 2012 in the Internet Archive )
  3. ↑ Gerrard, W .; Hudson, HR; Murphy, WS: s-Butyl Chloride from n-Butyl Dichloroborinate and from n-Butanol-Hydrogen Chloride. In: J. Chem. Soc. 1962 , 1099-1101, doi: 10.1039 / JR9620001099 .
  4. ^ Ullmann's Encyclopedia of Industrial Chemistry, Wiley Interscience, Release 2009, 7th Edition.