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1,2-Dibromobenzene (o-dibromobenzene) is an aryl bromide and isomer of dibromobenzene. It is one of three isomers, the others being 1,3- and 1,4-dibromobenzene. It is a colorless liquid, although impure samples appear yellowish. The compound is a precursor to many 1,2-disubstituted derivatives of benzene.
Dibromobenzene isomers Common name and systematic name 1,2-Dibromobenzene: 1,3-Dibromobenzene [1] 1,4-Dibromobenzene [2] [3] [4] Structure Molecular formula: C 6 H 4 Br 2: Molar mass: 235.906 g/mol Appearance colorless liquid colorless liquid white solid CAS number [583-53-9] [108-36-1] [106-37-6] Properties Density and phase: 1.9940 g/ml ...
Bromobenzenes are a group of aryl bromides/halobenzenes consisting of one or more bromine atoms as substituents on a benzene core. They have the formula C 6 H 6–n Br n, where n = 1–6 is the number of bromine atoms. Depending on the number of bromine substituents, there may be several constitutional isomers possible.
The most widely used synthetic route to DBA utilizes electrophilic borylation chemistry as the key transformation, [6] [7] which dates to 1969 from Seibert et al. [8] and 1998 from Eisch et al. [9] Starting with the commercially available chemical 1,2-dibromobenzene, lithium-halogen exchange [10] followed by silylation yields 1,2-bis(trimethylsilyl) benzene as the intermediate.
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1,4-Dibromobenzene (p-dibromobenzene) is an aryl bromide and isomer of dibromobenzene that is solid at room temperature. It has a strong smell similar to that of the lighter chlorine analogue. It can be used as a precursor to the dye 6,6-dibromoindigo. [4]
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 .
2 → C 6 H 4 Cl 2 + HCl. The reaction also affords the 1,4- and small amounts of the 1,3-isomer. The 1,4- isomer is preferred over the 1,2- isomer due to steric hindrance. The 1,3- isomer is uncommon because it is a meta- compound, while chlorine, like all halogens, is an ortho/para-director in terms of electrophilic aromatic substitution.