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
Names
IUPAC name
1,3-Dibromopropane[1]
Other names
Identifiers
635662
109-64-8 YesY
ChemSpider 7710 YesY
EC number 203-690-3
Jmol-3D images Image
MeSH 1,3-dibromopropane
PubChem 8001
RTECS number TX8575000
UNII YQR3048IX9 YesY
UN number 1993
Properties
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
11 μmol Pa−1 kg−1
1.524
Thermochemistry
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
H226, H302, H315, H411
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)
315 mg kg−1 (oral, rat)
Related compounds
Related alkanes
Related compounds
Mitobronitol
Except where noted otherwise, data is 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.