312968-33-5

Basic information

• Product Name: 1,1'-Biphenyl, 2,2'-dibroMo-
• Synonyms: 1,1'-Biphenyl, 2,2'-dibroMo-;2,2'-Biphenyldiboronic acid;B,B'-[1,1'-Biphenyl]-2,2'-diylbisboronic acid;[1,1'-Biphenyl]-2,2'-diyldiboronic acid;[2-(2-boronophenyl)phenyl]boronic acid
• CAS NO: 312968-33-5
• Molecular Formula: C₁₂H₁₂B₂O₄
• Molecular Weight: 311.99992
• Mol File: 312968-33-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 544.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.31
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.21±0.58(Predicted)
• CAS DataBase Reference: 1,1'-Biphenyl, 2,2'-dibroMo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Biphenyl, 2,2'-dibroMo-(312968-33-5)
• EPA Substance Registry System: 1,1'-Biphenyl, 2,2'-dibroMo-(312968-33-5)

Safety Data

• Hazardous Substances Data: 312968-33-5(Hazardous Substances Data)

Usage

General Description

1,1'-Biphenyl, 2,2'-dibromo-, also known as 4,4'-Dibromobiphenyl, is a chemical compound with the molecular formula C12H8Br2. It is a white to off-white solid that is insoluble in water but soluble in most organic solvents. 1,1'-Biphenyl, 2,2'-dibromo- is primarily used as an intermediate in the manufacturing of other chemicals, such as pharmaceuticals, pesticides, and dyes. It is also used as a research and development chemical for various applications. The compound is considered to have low toxicity and is not thought to be carcinogenic. However, it should be handled with care and proper safety measures should be followed when using or handling this chemical.

Upstream product

• 150-46-9 triethyl borate 
• 13029-09-9 2,2'-dibromobiphenyl 
• 7732-18-5 water 
• 92-52-4 biphenyl 
• 121-43-7 Trimethyl borate 
• 398128-09-1 2,2'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl 

Downstream Products

• 398128-09-1 2,2'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl 
• 869357-89-1 2,2'-bis(3-ditolylaminophenyl)-1,1'-biphenyl 
• 152952-99-3 (R,S)-2,2'-bis(2-1H-indenyl)-1,1'-biphenyl 

Relevant articles and documents

Hydroxytetraphenylenes as Chiral Ligands: Application to Asymmetric Darzens Reaction of Diazoacetamide with Aldehydes

Hydroxytetraphenylenes with rigid conformations are potential candidates for employment as chiral ligands in asymmetric synthesis. Highly diastereo- and enantioselective Darzens reactions between aldehydes and diazo-N,N-dimethylacetamide were found to be catalyzed by a chiral titanium complex formed in situ from Ti(O i Pr)4 and chiral 1,16-dihydroxytetraphenylene, leading to the formation of cis-glycidic amides in moderate to high yields with excellent enantiomeric purities (40-99% yield, up to 99% ee).

A Suzuki coupling based route to 2,2′-bis(2-indenyl)biphenyl derivatives

Because of the promising performance in olefin polymerization of 2,2′-bis(2-indenyldiyl)biphenyl zirconium dichloride, we developed a new and broadly applicable route to 2,2′-bis(2-indenyl)biphenyl derivatives. Reaction of the known 2,2′-diiodobiphenyl (26) with the new 2-indenyl boronic acid (23) did not result in the desired 2,2′-bis(2-indenyl)biphenyl (10); instead an isomer thereof, (spiro-1,1-(2,2′-biphenyl)-2-(2-indenyl)indane) (27), was obtained. It was found that compound 10 could be made via a palladium-catalyzed reaction of 2,2-biphenyldiboronic acid (31) with 2-bromoindene (21) under standard Suzuki reaction conditions. However, the yield of this reaction was low at low palladium catalyst loadings, due to a competitive hydrolysis reaction of 2,2-biphenyldiboronic acid (31). HTE techniques were used to find an economically viable protocol. Thus, use of the commercially available 1.0 molar solution of (n-Bu)4NOH in methanol with cosolvent toluene led to precipitation of the pure product in a fast and clean reaction, using only 0.7 mol % (0.35 mol % per C-C) of the expensive palladium catalyst.