269410-06-2

Basic information

• Product Name: 1-BROMO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE
• Synonyms: 1-Bromo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 2-Bromophenylboronic Acid Pinacol Ester;1-BROMO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE;2-(2-BROMOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• CAS NO: 269410-06-2
• Molecular Formula: C₁₂H₁₆BBrO₂
• Molecular Weight: 282.97
• Product Categories: B (Classes of Boron Compounds);Boronic Acids Esters
• Mol File: 269410-06-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 332.4°C at 760 mmHg
• Flash Point: 154.8°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.000283mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 1-BROMO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE(269410-06-2)
• EPA Substance Registry System: 1-BROMO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE(269410-06-2)

Safety Data

• Hazardous Substances Data: 269410-06-2(Hazardous Substances Data)

Usage

General Description

1-Bromo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene is a chemical compound with the molecular formula C12H15BO2Br. It is commonly used in organic synthesis as a reagent for the introduction of the boronic ester functional group into organic molecules. 1-BROMO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE has a benzene ring with a bromine atom attached at the 1-position and a 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) group attached at the 2-position. 1-Bromo-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene is a versatile building block in organic synthesis and is often used in the preparation of pharmaceuticals, agrochemicals, and materials science applications.

InChI:InChI=1/C12H16BBrO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8H,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 615-36-1 2-bromoaniline 
• 22092-92-8 diisopropopylaminoborane 
• 10448-07-4 2-bromobenzenediazonium tetrafluoroborate 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 583-53-9 2,3-dibromobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 269410-07-3 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene 
• 109306-86-7 2-(2-Bromophenyl)pyridine 
• 392-83-6 o-trifluoromethylphenyl bromide 
• 15861-49-1 1-bromo-2-(4-methylphenylsulfanyl)benzene 
• 217-59-4 triphenylene 
• 447405-58-5 [Pd(η2-C6H4)(PPh3)2] 
• 114907-51-6 [η²-benzyne][1,2-bis(dicyclohexylphosphino)ethane]nickel(0) 
• 447405-44-9 trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II) 
• 447405-46-1 cis-bromo[1,2-bis(dicyclohexylphosphino)ethane][2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]nickel(II) 
• 447405-51-8 [PdBr(o-C₆H₄B(pinacolate))(1,2-bis(dicyclohexylphosphino)ethane)] 
• 446874-86-8 [Pd(η2-C6H4)(P(C6H11)3)2] 

Relevant articles and documents

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Radical Metal-Free Borylation of Aryl Iodides

A simple metal-free borylation of aryl iodides mediated by a fluoride sp 2 -sp 3 diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine serves to stabilize the boryl radicals, generated in situ.

Palladium(I) Dimer Enabled Extremely Rapid and Chemoselective Alkylation of Aryl Bromides over Triflates and Chlorides in Air

Disclosed herein is the first general chemo- and site-selective alkylation of C?Br bonds in the presence of COTf, C?Cl and other potentially reactive functional groups, using the air-, moisture-, and thermally stable dinuclear PdI catalyst, [Pd(μ-I)PtBu3]2. The bromo-selectivity is independent of the substrate and the relative positioning of the competing reaction sites, and as such fully predictable. Primary and secondary alkyl chains were introduced with extremely high speed (5 min reaction time) at room temperature and under open-flask reaction conditions.