1,3-Dibromopropane

1,3-Dibromopropane
Identifiers
CAS number 109-64-8 Y
ChemSpider 7710 Y
UNII YQR3048IX9 Y
Jmol-3D images Image 1
Properties
Molecular formula C3H6Br2
Molar mass 201.89 g/mol
Appearance Colorless to slightly-yellow liquid
Density 1.98 g/mL, liquid
Melting point

-34 °C, 239 K, -29 °F

Boiling point

166-167 °C (439 - 440 K)

Hazards
GHS pictograms [1]
GHS hazard statements H226, H302, H315, H411[1]
GHS precautionary statements P273
R-phrases R10 R22 R38 R51 R53
S-phrases S16 S26 S36 S61
Flash point 56 °C (closed cup)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,3-Dibromopropane is a halogenated hydrocarbon. When at room temperature, it is a colorless to light-brown liquid. Synthetically, it is very useful to form C3-bridged compounds such as through C-N coupling reactions.

1,3-Dibromopropane was used in the first cyclopropane synthesis in 1881, the Freund reaction.[2]

Synthesis

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.[3]

References

  1. ^ a b Online Sigma Catalogue , accessdate: June 10, 2011.
  2. ^ August Freund (1881). "Über Trimethylen". Journal für Praktische Chemie 26 (1): 625–635. doi:10.1002/prac.18820260125. 
  3. ^ W. E. Vaughan, F. F. Rust, T. W. Evans (1942). "The photo-addition of hydrogen bromide to olefinic bonds". J. Org. Chem. 7 (6): 477–490. doi:10.1021/jo01200a005.