1,3-Dibromopropane

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1,3-Dibromopropane
1,3-dibromopropane
IUPAC name 1,3-dibromopropane
Other names trimethylenebromide
Identifiers
CAS number [109-64-8]
SMILES
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)

Boiling point

166-167 °C (439 - 440 K)

Solubility in water  ? g/100 ml (?°C)
Viscosity  ? cP at ?°C
Hazards
R-phrases R10 R22 R38 R51 R53.
S-phrases S16 S26 S36 S61.
Flash point 56 °C (closed cup)
Related compounds
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.[1]

Synthesis

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.[2]

References

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

This article is from Wikipedia. All text is available under the terms of the GNU Free Documentation License.


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