1,3-Dibromobenzene

1,3-Dibromobenzene

Names
IUPAC name 1,3-Dibromobenzene
Other names m-Dibromobenzene
Identifiers
CAS Number	108-36-1
3D model (JSmol)	Interactive image
Beilstein Reference	1904538
ChEBI	CHEBI:37151
ChemSpider	13875356
ECHA InfoCard	100.003.250
EC Number	203-574-2
Gmelin Reference	363342
PubChem CID	7927
UNII	74EF6KH8TC
CompTox Dashboard (EPA)	DTXSID7051555
InChI InChI=1S/C6H4Br2/c7-5-2-1-3-6(8)4-5/h1-4H Key: JSRLURSZEMLAFO-UHFFFAOYSA-N
SMILES C1=CC(=CC(=C1)Br)Br
Properties
Chemical formula	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	1,2-Dibromobenzene 1,4-Dibromobenzene 1,3-Dichlorobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

Preparation

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

Uses

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

• 1,2-Dibromobenzene
• 1,4-Dibromobenzene

References

1. "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.