2-bromobutane

Structural formula
	Structural formula without stereochemistry
General
Surname	2-bromobutane
other names	sec-butyl bromide
Molecular formula	C 4 H 9 Br
Brief description	Flammable, volatile, colorless liquid with an aromatic odor
External identifiers / databases
EC number	201-140-7
ECHA InfoCard	100.001.037
PubChem	6554
Wikidata	Q209314
properties
Molar mass	137.02 g mol −1
Physical state	liquid
density	1.26 g cm −3
Melting point	−112 ° C
boiling point	91 ° C
Vapor pressure	73.3 h Pa (20 ° C); 116 hPa (30 ° C); 177 hPa (40 ° C); 262 hPa (50 ° C);
solubility	practically insoluble in water (<1 g l −1 at 20 ° C); soluble in ethanol and ether;
Refractive index	1.437 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 225-412
	P: 210-233-240-273-403 + 235
	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-Bromobutane is a chemical compound from the group of aliphatic halogenated hydrocarbons and organic bromine compounds . It is isomeric to 1-bromobutane , isobutyl bromide and tert-butyl bromide and belongs to the group of butyl bromides .

Isomers

It occurs in two enantiomeric forms, ( R ) -2-bromobutane and ( S ) -2-bromobutane.

Isomers of 2-bromobutane
Surname	( S ) -2-bromobutane	( R ) -2-bromobutane
other names	(+) - 2-bromobutane	(-) - 2-bromobutane
Structural formula
CAS number	5787-32-6	5787-33-7
	78-76-2 (unspec.)
EC number	-	-
	201-140-7 (unspec.)
ECHA info card	-	-
	100.001.037 (unspec.)
PubChem	12236140	637147
	6554 (unspec.)
Wikidata	Q27254482	Q27252707
	Q209314 (unspec.)

Extraction and presentation

2-Bromobutane can be obtained by reacting 1-butene , 2-butene or 2-butanol with hydrogen bromide .

{\ displaystyle \ mathrm {C_ {4} H_ {8} + HBr \ longrightarrow C_ {4} H_ {9} Br}}

{\ displaystyle \ mathrm {C_ {4} H_ {9} OH + HBr \ longrightarrow C_ {4} H_ {9} Br + H_ {2} O}}

properties

2-bromobutane forms highly flammable vapor-air mixtures. The compound has a flash point of 21 ° C. The explosion range is between 2.6 vol.% As the lower explosion limit (LEL) and 6.6 vol.% As the upper explosion limit (UEL). The ignition temperature is 265 ° C. The substance therefore falls into temperature class T3.

use

2-bromobutane is used in the manufacture of medicines and fragrances (to introduce the butyl group ).

Web links

uni-regensburg.de: Reaction of the isomeric butyl bromides with AgNO ₃ (learning objective: nucleophilic substitution - SN ₁ and SN ₂ ) by Peter Keusch.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 2-bromobutane in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Data sheet 2-bromobutane (PDF) from Merck , accessed on July 9, 2010.
↑ 2-Bromobutane data sheet from Sigma-Aldrich , accessed on July 22, 2013 ( PDF ).

^ Francis A. Carey; Organic Chemistry , ISBN 0-07-290501-8 , pp. 215, p. 275.

↑ ^a ^b ^c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 2-bromobutane in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[merck-2] Data sheet 2-bromobutane (PDF) from Merck , accessed on July 9, 2010.

[Sigma-3] 2-Bromobutane data sheet from Sigma-Aldrich , accessed on July 22, 2013 ( PDF ).

[4] Francis A. Carey; Organic Chemistry , ISBN 0-07-290501-8 , pp. 215, p. 275.

[Brandes-5] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.