60108-72-7

Usage

Uses

Used in Organic Synthesis:
1,2-dibromo-4-phenyl-benzene serves as a fundamental building block in organic synthesis, facilitating the creation of more intricate molecular structures. Its symmetrical and reactive nature makes it a valuable component in the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1,2-dibromo-4-phenyl-benzene is employed as an intermediate. It plays a crucial role in the development and manufacturing of various pharmaceuticals, contributing to the formation of active ingredients or key components of drug formulations.
Used in Agrochemical Production:
Similarly, in agrochemicals, 1,2-dibromo-4-phenyl-benzene is utilized as an intermediate. It aids in the synthesis of compounds that are integral to the development of pesticides, herbicides, and other agricultural chemicals, enhancing crop protection and yield.
Given its applications and the moderate hazard classification, it is imperative that 1,2-dibromo-4-phenyl-benzene is managed with appropriate safety protocols to ensure the well-being of individuals and the environment.

InChI:InChI=1/C12H8Br2/c13-11-7-6-10(8-12(11)14)9-4-2-1-3-5-9/h1-8H

Upstream product

• 91394-63-7 4-bromo-biphenyl-3-ylamine 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 615-55-4 3,4-dibromoaniline 
• 71-43-2 benzene 
• 98-80-6 phenylboronic acid 
• 591-19-5 m-Bromoaniline 
• 4085-18-1 4-amino-3-nitrobiphenyl 
• 27701-66-2 4-bromo-3-nitrobiphenyl 

Downstream Products

• 92-66-0 4-bromo-1,1'-biphenyl 
• 2113-57-7 3-bromobiphenyl 
• 1266379-54-7 (4,5-dibromobiphenyl-3-yl)trimethylsilane 
• 1267964-81-7 C₂₀H₁₇BrO₂ 
• 1267964-79-3 4'-bromo-2'',6''-dimethoxy-[1,1';3',1'']terphenyl 
• 1369371-71-0 4-phenyl-1,2-bis(trimethylsilyl)benzene 

Relevant academic research and scientific papers

Efficient and complementary methods offering access to synthetically valuable 1,2-dibromobenzenes

1,2-Dibromobenzenes are highly valuable precursors for various organic transformations, in particular, reactions based on the intermediate formation of benzynes. This report describes short sequences for the synthesis of various derivatives based on regioselective bromination, ortho-metalation, and halogen/metal permutations. 1,2-Dibromo-3-iodobenzene (2f), 1,2-dibromo-4- iodobenzene (4c), and 2,3-dibromo-1,4-diiodobenzene (5e) act as intermediates in these syntheses. Bromo-iodoarenes have been synthesized by short and regioselective bromination or iodination sequences that combine ortho-metalation, halo-desilylation, diazotation, or bromination reactions of anilines. These polyhalo derivatives were then used as key intermediates to access a wide range of functionalized 1,2-dibromobenzenes by chemoselective organometallic reactions. Copyright

The photochemistry of polyhaloarenes XIII. The photohydrodehalogenation of 3,4-dibromobiphenyl

Irradiation of 3,4-dibromobiphenyl (BpBr2) in acetonitrile resulted in the formation of 4-bromobiphenyl (BpBr) and 3- bromobiphenyl (3-BpBr) in a ratio of 7.6 ± 0.1 up to 22% conversion of starting material. The dependence of the reciprocal of the quantum yield (1/Φ) upon 1/BpBr2 is linear. Reduction of BpBr2 with lithium di-tert-butylbiphenylide generates a 3.6:1.0 ratio of BpBr to 3-BpBr, while photohydrodebromination of BpBr2 in the presence of triethylamine produces a similar ratio of 1.8:1.0. Product determining radical stability was assessed by radical debromination of BpBr2 using Ph3SnH in THF, which resulted in a BpBr:3-BpBr ratio of 1.5:1.0 AMI calculations on the product determining radicals provide the basis for rationalization of products via excimer and radical anion intermediates.

Synthetically Useful Aryl-Aryl Bond Formation via Grignard Generation and Trapping of Arynes. A One Step Synthesis of p-Terphenyl and Unsymmetric Biaryls

A one-pot route to p-terphenyls is described.Addition of 1,4-dibromo-2,5-diiodobenzene, 1, to excess aryl Grignard reagent gives the terphenyl di-Grignard 2 and the trihalo mono-Grignard 5.After aqueous quench, p-terphenyls are isolated in 30percent to 50percent yield (Table I).This yield can be improved to 70-80percent by adding potassium tert-butoxide or lithium tetramethylpiperidide to the reaction mixture prior to workup.Mechanisms involving organometallic aryne intermediates are proposed.With o-bromoiodoarenes in place of tetrahaloarenes the method can be adapted to prepare unsymmetric biaryls in good yield (Table II).