60108-72-7

Basic information

• Product Name: 1,2-dibromo-4-phenyl-benzene
• Synonyms: 1,2-dibromo-4-phenyl-benzene
• CAS NO: 60108-72-7
• Molecular Formula: C₁₂H₈Br₂
• Molecular Weight: 312.00000
• Mol File: 60108-72-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 350.2oC at 760 mmHg
• Flash Point: 192.9oC
• Appearance: /
• Density: 1.667g/cm3
• Vapor Pressure: 9.02E-05mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 1,2-dibromo-4-phenyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dibromo-4-phenyl-benzene(60108-72-7)
• EPA Substance Registry System: 1,2-dibromo-4-phenyl-benzene(60108-72-7)

Safety Data

• Hazardous Substances Data: 60108-72-7(Hazardous Substances Data)

Usage

General Description

1,2-dibromo-4-phenyl-benzene is a chemical compound with the molecular formula C12H8Br2. It is a symmetrical molecule consisting of a benzene ring with two bromine atoms attached at the 1 and 2 positions, and a phenyl group attached at the 4 position. 1,2-dibromo-4-phenyl-benzene is used in organic synthesis as a building block for the construction of more complex molecules. It is also used as an intermediate in the production of pharmaceuticals and agrochemicals. 1,2-dibromo-4-phenyl-benzene is a white to off-white solid at room temperature and has a melting point of 217-219°C. It is considered to be a moderate hazard chemical and should be handled with proper safety precautions.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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

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).