428820-95-5

Basic information

• Product Name: 2-(3,5-Dinitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(3,5-Dinitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3,5-Dinitrophenylboronic acid, pinacol ester
• CAS NO: 428820-95-5
• Molecular Formula: C₁₂H₁₅BN₂O₆
• Molecular Weight: 294.07
• Mol File: 428820-95-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 147.0 to 151.0 °C
• Appearance: /
• CAS DataBase Reference: 2-(3,5-Dinitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,5-Dinitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(428820-95-5)
• EPA Substance Registry System: 2-(3,5-Dinitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(428820-95-5)

Safety Data

• Hazardous Substances Data: 428820-95-5(Hazardous Substances Data)

Usage

General Description

2-(3,5-dinitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound belonging to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system made up of benzene. This specific compound has a structure with two nitro groups attached to a benzene ring, bonded to a 1,3,2-dioxaborolane group. The 1,3,2-dioxaborolane group is a heterocyclic compound which comprises a boron atom linked to two oxygen atoms and two carbon atoms in a five-membered ring system, and this ring system is substituted with four methyl groups. The detailed properties of the chemical such as physical state, melting and boiling points or solubility can be determined via specific tests or computational chemistry models.

Upstream product

• 6276-04-6 3,5-dinitroiodobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 618-87-1 3, 5-dinitroaniline 

Downstream Products

• 912818-48-5 4'-[2''-deoxy-5''-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-3,5-dinitrobiphenyl 

Relevant articles and documents

Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion

Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso protonation of the boronate as the mechanism for base-catalyzed protodeboronation of arylboronic acids. However, the study was limited to UV spectrophotometric analysis under acidic conditions, and the aqueous association constants (Ka) were estimated. By means of NMR, stopped-flow IR, and quenched-flow techniques, the kinetics of base-catalyzed protodeboronation of 30 different arylboronic acids has now been determined at pH > 13 in aqueous dioxane at 70 °C. Included in the study are all 20 isomers of C6HnF(5-n)B(OH)2 with half-lives spanning 9 orders of magnitude: a and Sδ values, kinetic isotope effects (2H, 10B, 13C), linear free-energy relationships, and density functional theory calculations, we have identified a mechanistic regime involving unimolecular heterolysis of the boronate competing with concerted ipso protonation/C-B cleavage. The relative Lewis acidities of arylboronic acids do not correlate with their protodeboronation rates, especially when ortho substituents are present. Notably, 3,5-dinitrophenylboronic acid is orders of magnitude more stable than tetra-and pentafluorophenylboronic acids but has a similar pKa.

Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides

We describe the synthesis of eight novel C-nucleosides in which the nucleobases are replaced by biphenyl residues that carry one or two electron donor (-OCH3, -NH2) or acceptor (-NO2) functional groups in the distal ring. These C-nucleosides were synthesized convergently and in high yields from a common bromophenyl-C-nucleoside precursor via Suzuki coupling with the respective boronic acids or esters. These nucleosides were subsequently converted into the corresponding phosphoramidite building blocks and efficiently incorporated into oligodeoxynucleotides by standard phosphoramidite chemistry.