1,3-Dibromopropane

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1,3-Dibromopropane
Skeletal formula of 1,3-dibromopropane
Ball and stick model of 1,3-dibromopropane Spacefill model of 1,3-dibromopropane
Identifiers
CAS number 109-64-8 YesY
PubChem 8001
ChemSpider 7710 YesY
UNII YQR3048IX9 YesY
EC number 203-690-3
UN number 1993
MeSH 1,3-dibromopropane
RTECS number TX8575000
Beilstein Reference 635662
Jmol-3D images Image 1
Properties
Molecular formula C3H6Br2
Molar mass 201.89 g mol−1
Appearance Colorless liquid
Density 1.989 g mL−1
Melting point −34.20 °C; −29.56 °F; 238.95 K
Boiling point 167 °C; 332 °F; 440 K
kH 11 μmol Pa−1 kg−1
Refractive index (nD) 1.524
Thermochemistry
Specific
heat capacity
C
163.7 J K mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
GHS hazard statements H226, H302, H315, H411
GHS precautionary statements P273
EU classification Harmful Xn Dangerous for the Environment (Nature) N
R-phrases R10, R22, R38, R51/53
S-phrases S16, S26, S36
Flash point 56 °C (133 °F; 329 K)
LD50 315 mg kg−1 (oral, rat)
Related compounds
Related alkanes
Related compounds Mitobronitol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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, known as the Freund reaction.[2]

Synthesis[edit]

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

References[edit]

  1. ^ "1,3-dibromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 21 June 2012. 
  2. ^ August Freund (1882). "Ueber Trimethylen". Journal für Praktische Chemie 26 (1): 367–377. 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". Journal of Organic Chemistry 7 (6): 477–490. doi:10.1021/jo01200a005.