479411-96-6

Basic information

• Product Name: 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile
• Synonyms: 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile;3-Bromo-5-cyanophenylboronic acid pinacol ester;3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
• CAS NO: 479411-96-6
• Molecular Formula: C₁₃H₁₅BBrNO₂
• Molecular Weight: 307.9787
• Mol File: 479411-96-6.mol

Chemical Properties

• Boiling Point: 374.2±32.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile(479411-96-6)
• EPA Substance Registry System: 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile(479411-96-6)

Safety Data

• Hazardous Substances Data: 479411-96-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile is used as a key intermediate in the synthesis of various biologically active molecules for the development of new pharmaceuticals. Its unique structure allows for the creation of diverse organic compounds with potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile is employed as a building block for the design and synthesis of potential anticancer agents and other therapeutic compounds. Its versatility in chemical reactions contributes to the exploration of novel molecular structures with improved pharmacological properties.
Used in Organic Synthesis:
3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile is utilized as a valuable reagent in organic synthesis, facilitating the formation of complex molecular structures. Its bromine atom and benzonitrile group provide opportunities for further functionalization, while the boron-containing dioxaborolane moiety offers unique reaction pathways, making it an essential component in the synthesis of a wide array of organic compounds.

Upstream product

• 6952-59-6 3-cyanobromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1352304-67-6 5'-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-3-ethoxycarbonyl-3''-methoxy-1,1':3',1''-terphenyl 
• 1130011-42-5 C₁₅H₁₀BrNO₂ 

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.

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization

Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as clopidogrel.

Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp2 C-H borylation reaction. A symmetric pyridine-con

ALKYNYL ALCOHOLS AND METHODS OF USE

The invention relates to compounds of Formula (0): wherein Q, A1-A8, R4 and R5 and each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over- activation of NF-kB signaling is observed.

Rhodium(I)-catalyzed borylation of nitriles through the cleavage of carbon-cyano bonds

The reaction of aryl cyanides with diboron in the presence of a rhodium/Xantphos catalyst and DABCO affords arylboronic esters via carbon-cyano bond cleavage. This unprecedented mode of reactivity for a borylrhodium species allows the regioselective intro

A one-pot, single-solvent process for tandem, catalyzed C-H borylation-Suzuki-Miyaura cross-coupling sequences

Methyl tert-butyl ether is a suitable solvent for iridium-catalyzed C-H borylation followed, in the same pot, by palladium-catalyzed Suzuki-Miyaura cross-coupling sequences, giving high yields of biaryls. Georg Thieme Verlag Stuttgart.

Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent

Aromatic C-H borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane was catalyzed by an iridium complex generated from 1/2 [Ir(OMe)(COD)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine at room temperature in hexane and aff

A stoichiometric aromatic C-H borylation catalyzed by iridium(I)/2,2′-bipyridine complexes at room temperature

Room-temperature C-H borylation using a stoichiometric amount of arenes and bis(pinacolato)diboron (pin2B2) is efficiently catalyzed by iridium(I) complexes generated from [{Ir(OMe)(cod)}2] (cod=1,5-cyclooctadiene) and 4,4′-di-tertbutyl-2,2′-bipyridine (dtbpy) in hexane, and provides the corresponding arylboronates in excellent yields [Eq. (1)].