1,3-Dibromobenzene (m-dibromobenzene) is an aryl bromide and isomer of dibromobenzene that is a colorless liquid at room temperature.[1]

1,3-Dibromobenzene
Names
IUPAC name
1,3-Dibromobenzene
Other names
m-Dibromobenzene
Identifiers
3D model (JSmol)
1904538
ChEBI
ChemSpider
ECHA InfoCard 100.003.250 Edit this at Wikidata
EC Number
  • 203-574-2
363342
UNII
  • InChI=1S/C6H4Br2/c7-5-2-1-3-6(8)4-5/h1-4H
    Key: JSRLURSZEMLAFO-UHFFFAOYSA-N
  • C1=CC(=CC(=C1)Br)Br
Properties
C6H4Br2
Molar mass 235.906 g·mol−1
Appearance colorless liquid[1]
Density 1.9523 g/cm3 at 20.4 °C
Melting point −7.0 °C (19.4 °F; 266.1 K)
Boiling point 218–220 °C (424–428 °F; 491–493 K)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Preparation

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1,3-Dibromobenzene may be prepared by diazotization of 3-bromoaniline, followed by a Sandmeyer reaction with cuprous bromide.[2]

Uses

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1,3-Dibromobenzene has been used as a starting material in the synthesis of antiviral Lufotrelvir, in human clinical trials for the treatment of COVID-19.[3] The first step is formylation of 1,3-dibromobenzene to 2,6-dibromobenzaldehyde, by lithiation with lithium diisopropylamide in THF, followed by quenching with dimethylformamide.

 

See also

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References

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  1. ^ a b "1,3-Dibromobenzene". PubChem.
  2. ^ Hartwell, Jonathan L. (1944). "o-Chlorobromobenzene". Organic Syntheses. 24: 22. doi:10.15227/orgsyn.024.0022.
  3. ^ Allais, Christophe; Bernhardson, David; Brown, Adam R.; Chinigo, Gary M.; Desrosiers, Jean-Nicolas; Dirico, Kenneth J.; Hotham, Ian; Jones, Brian P.; Kulkarni, Samir A.; Lewis, Chad A.; Lira, Ricardo; Loach, Richard P.; Morse, Peter D.; Mousseau, James J.; Perry, Matthew A.; Peng, Zhihui; Place, David W.; Rane, Anil M.; Samp, Lacey; Singer, Robert A.; Wang, Zheng; Weisenburger, Gerald A.; Yayla, Hatice G.; Zanghi, Joseph M. (3 February 2023). "Early Clinical Development of Lufotrelvir as a Potential Therapy for COVID-19". Organic Process Research & Development. 27 (12): 2223–2239. doi:10.1021/acs.oprd.2c00375. PMID 37552749. S2CID 256584424.{{cite journal}}: CS1 maint: date and year (link)