479411-92-2

Basic information

• Product Name: 3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol ester
• Synonyms: 3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol ester;(3-BROMO-5-(TRIFLUOROMETHYL)PHENYL)BORONIC ACID PINACOL ESTER
• CAS NO: 479411-92-2
• Molecular Formula: C₁₃H₁₅BBrF₃O₂
• Molecular Weight: 350.969
• Mol File: 479411-92-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 50-52℃
• Boiling Point: 333.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol ester(479411-92-2)
• EPA Substance Registry System: 3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol ester(479411-92-2)

Safety Data

• Hazardous Substances Data: 479411-92-2(Hazardous Substances Data)

Usage

Uses

Used as a active pharmaceutical ingredient.

Upstream product

• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 630125-49-4 1-bromo-3-nitro-5-(trifluoromethyl)benzene 
• 366-04-1 3-(trifluoromethyl)biphenyl 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 

Relevant articles and documents

Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.

NNB-type tridentate boryl ligands enabling a highly active iridium catalyst for C–H borylation

Boryl ligands play a very important role in catalysis because of their very high electron-donating property. In this paper, NNB-type boryl anions were designed as tridentate ligands to promote aryl C–H borylation. In combination with [IrCl(COD)]2/su

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.