1,3-Dibromopropane

1,3-Dibromopropane
Names
IUPAC name
1,3-Dibromopropane[1]
Other names
  • Trimethylenebromide
  • Trimethylene dibromide
Identifiers
109-64-8 YesY
635662
ChemSpider 7710 YesY
EC Number 203-690-3
Jmol interactive 3D 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
GHS signal word WARNING
H226, H302, H315, H411
P273
Xn N
R-phrases R10, R22, R38, R51/53
S-phrases S16, S26, S36
Flash point 56 °C (133 °F; 329 K)
Lethal dose or concentration (LD, LC):
315 mg kg−1 (oral, rat)
Related compounds
Related alkanes
Related compounds
Mitobronitol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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

References

  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.
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