474709-28-9

Basic information

• Product Name: 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE
• Synonyms: 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE;4-(TRIFLUOROMETHOXY)PHENYLBORONIC ACID, PINACOL ESTER;5-TetraMethyl-2-(4-trifluoroMethoxyphenyl)-1
• CAS NO: 474709-28-9
• Molecular Formula: C₁₃H₁₆BF₃O₃
• Molecular Weight: 288.07
• Mol File: 474709-28-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 61-62°C
• Boiling Point: 293.2°C at 760 mmHg
• Flash Point: 131.1°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.00306mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE(474709-28-9)
• EPA Substance Registry System: 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE(474709-28-9)

Safety Data

• Hazard Codes: T
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 474709-28-9(Hazardous Substances Data)

Usage

General Description

4,4,5,5-Tetramethyl-2-(4-trifluoromethoxyphenyl)-1,3,2-dioxaborolane is a chemical compound that contains a boron atom and is commonly used in organic synthesis and pharmaceutical research. It is a boronic ester derivative with a unique molecular structure. 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE is often employed as a reagent for Suzuki-Miyaura cross-coupling reactions, which are widely used in the synthesis of various pharmaceuticals and fine chemicals. Additionally, the trifluoromethoxyphenyl group attached to the boron atom provides unique reactivity and can enable the selective functionalization of organic molecules. Due to its versatile reactivity and potential applications in organic synthesis, 4,4,5,5-Tetramethyl-2-(4-trifluoromethoxyphenyl)-1,3,2-dioxaborolane is an important and valuable chemical compound in the field of organic and medicinal chemistry.

InChI:InChI=1/C13H16BF3O3/c1-11(2)12(3,4)20-14(19-11)9-5-7-10(8-6-9)18-13(15,16)17/h5-8H,1-4H3

Upstream product

• 461-82-5 4-(trifluoromethoxy)aniline 
• 73183-34-3 bis(pinacol)diborane 
• 330-12-1 4-trifluoromethoxybenzoic acid 
• 87750-51-4 1-(methylsulfonyl)-4-(trifluoromethoxy)benzene 
• 2402-62-2 N,N-dimethyl-4-(trifluoromethoxy) aniline 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 56465-82-8 C₁₁H₁₁F₃O₂ 
• 659-28-9 p-trifluoromethoxybenzaldehyde 
• 461-81-4 1-chloro-4-(trifluoromethoxy)benzene 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 103962-05-6 1-iodo-4-(trifluoromethoxy)benzene 
• 407-14-7 1-bromo-4-(trifluoromethoxy)benzene 
• 456-55-3 1-trifluoromethoxybenzene 

Downstream Products

• 1440059-09-5 C₁₄H₁₁F₃O₂ 
• 1379615-30-1 7-methoxy-3-methyl-2-(5-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)quinolin-4(1H)-one 
• 1379615-51-6 1-(5-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-propan-1-one 
• 80258-33-9 1-(trifluoromethoxy)-4-(trifluoromethyl)benzene 
• 238431-33-9 (1R,2S)-2-(4-(trifluoromethoxy)phenyl)cyclopropane-1-carboxylic acid 
• 828-27-3 4-Trifluoromethoxyphenol 

Relevant articles and documents

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

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.