1,3-Dibromopropane

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 Trimethylenebromide[2]; Trimethylene dibromide[3];
Identifiers
CAS Number	109-64-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	635662
ChemSpider	7710 ;
ECHA InfoCard	100.003.356
EC Number	203-690-3;
MeSH	1,3-dibromopropane
PubChem CID	8001;
RTECS number	TX8575000;
UNII	YQR3048IX9 ;
UN number	1993
CompTox Dashboard (EPA)	DTXSID1021902 ;
	InChI InChI=1S/C3H6Br2/c4-2-1-3-5/h1-3H2 Key: VEFLKXRACNJHOV-UHFFFAOYSA-N ;
	SMILES BrCCCBr;
Properties
Chemical formula	C3H6Br2
Molar mass	201.889 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
Henry's law; constant (kH)	11 μmol Pa−1 kg−1
Refractive index (nD)	1.524
Thermochemistry
Heat capacity (C)	163.7 J K mol−1
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H302, H315, H411
GHS precautionary statements	P273
Flash point	56 °C (133 °F; 329 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	315 mg kg−1 (oral, rat)
Related compounds
Related alkanes	1,1-Dibromoethane; 1,2-Dibromoethane; Tetrabromoethane; 1,2-Dibromopropane; 1,2,3-Tribromopropane;
Related compounds	Mitobronitol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

1,3-Dibromopropane is an organobromine compound with the formula (CH₂)₃Br₂. It is a colorless liquid with sweet odor. It is used in organic synthesis 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.[4]

Synthesis

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.[5]

Metabolism

Metabolism of 1,3-dibromopropane was examined in 1981.[6] The examination was done by orally administering 1,3-dibromopropane to rats and collection results 24hours after administration. Results were obtained from three sources: urine, faeces, and expired air. Upon analysis of the urinary results, researchers discovered the formation of metabolite, N-acetyl-S-(1-bromo-3-propyl)-cysteine and the decline in the GSH content of the liver of the rats. This led to the assumption that 1,3-dibromopropane could have reacted with GSH after administration and gave rise to 1-bromo-3-propyl-S-glutathione, which ultimately form the urinary metabolite. Moreover, due to little radioactivity observed from feces and the confirmation from maintained blood levels of radioactivity proved the occurrence of biliary excretion of sulfur-containing metabolites and enterohepatic cycling.

gollark: Yes, 1.1 isn't part of the formatting code so it just prints the float then that.

gollark: Writing a bare metal microkernel in Haskell is not very practical.

gollark: > I never tried it. It's nice that it has these safety features but I prefer C++ still. > If I want to be sure that my program is free of bugs, I can write a formal specification and do a > correctness proof with the hoare calculus in some theorem proofer (People did that for the seL4 microkernel, which is free from bugs under some assumptions and used in satellites, nuclear power plants and such)Didn't doing that for seL4 require several hundred thousand lines of proof code?

gollark: Most countries have insanely convoluted tax law so I assume it's possible.

gollark: Hmm, so you need to obtain a hypercomputer of some sort to write your tax forms such that they cannot plausibly be checked?

References

"1,3-dibromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 21 June 2012.
Creese, Mary R. S. (2015). Ladies in the Laboratory IV: Imperial Russia's Women in Science, 1800-1900: A Survey of Their Contributions to Research. Rowman & Littlefield. p. 57. ISBN 978-1-4422-4742-0.
"1,3-Dibromopropane". pubchem.ncbi.nlm.nih.gov.
August Freund (1882). "Ueber Trimethylen". Journal für Praktische Chemie. 26 (1): 367–377. doi:10.1002/prac.18820260125.
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.
S. P. James; M. A. Put; D. H. Richards (1981). "Metabolism of 1,3-dibromopropane". Toxicology Letters. 8 (1–2): 7–15. doi:10.1016/0378-4274(81)90130-2.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] "1,3-dibromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 21 June 2012.

[2] Creese, Mary R. S. (2015). Ladies in the Laboratory IV: Imperial Russia's Women in Science, 1800-1900: A Survey of Their Contributions to Research. Rowman & Littlefield. p. 57. ISBN 978-1-4422-4742-0.

[3] "1,3-Dibromopropane". pubchem.ncbi.nlm.nih.gov.

[Freund81-4] August Freund (1882). "Ueber Trimethylen". Journal für Praktische Chemie. 26 (1): 367–377. doi:10.1002/prac.18820260125.

[5] 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.

[6] S. P. James; M. A. Put; D. H. Richards (1981). "Metabolism of 1,3-dibromopropane". Toxicology Letters. 8 (1–2): 7–15. doi:10.1016/0378-4274(81)90130-2.