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2-Bromobutane

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2-Bromobutane
Skeletal formula of 2-bromobutane
Names
Preferred IUPAC name 2-Bromobutane
Other names sec-Butylbromide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 505949
ChEMBL
ChemSpider
ECHA InfoCard 100.001.037 Edit this at Wikidata
EC Number
  • 201-140-7
MeSH 2-bromobutane
PubChem CID
RTECS number
  • EJ6228000
UNII
UN number 2339
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9Br/c1-3-4(2)5/h4H,3H2,1-2H3Key: UPSXAPQYNGXVBF-UHFFFAOYSA-N
SMILES
  • CCC(C)Br
Properties
Chemical formula C4H9Br
Molar mass 137.020 g·mol
Appearance Colourless liquid
Density 1.255 g mL
Melting point −112.65 °C; −170.77 °F; 160.50 K
Boiling point 91 °C; 196 °F; 364 K
log P 2.672
Refractive index (nD) 1.437
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		−156 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−2.706–−2.704 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable
Signal word Danger
Hazard statements H225
Precautionary statements P210
Flash point 21 °C (70 °F; 294 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Bromobutane is an isomer of 1-bromobutane. Both compounds share the molecular formula C4H9Br. 2-Bromobutane is also known as sec-butyl bromide or methylethylbromomethane. Because it contains bromine, a halogen, it is part of a larger class of compounds known as alkyl halides. It is a colorless liquid with a pleasant odor. Because the carbon atom connected to the bromine is connected to two other carbons the molecule is referred to as a secondary alkyl halide. 2-Bromobutane is chiral and thus can be obtained as either of two enantiomers designated as (R)-(−)-2-bromobutane and (S)-(+)-2-bromobutane.

2-Bromobutane is relatively stable, but is toxic and flammable. When treated with a strong base, it is prone to undergo an E2 reaction, which is a bimolecular elimination reaction, resulting in (predominantly) 2-butene, an alkene (double bond). 2-Bromobutane is an irritant, and harmful if ingested. It can irritate and burn skin and eyes.

References

  1. "2-bromob isutane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Retrieved 17 June 2012.
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