517920-59-1

Basic information

• Product Name: 2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• Synonyms: 2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;2-(3-Chlorobenzyl);(3-CHLOROBENZYL)BORONIC ACID PINACOL ESTER
• CAS NO: 517920-59-1
• Molecular Formula: C₁₃H₁₈BClO₂
• Molecular Weight: 252.54482
• Mol File: 517920-59-1.mol

Chemical Properties

• Boiling Point: 298.8±23.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(517920-59-1)
• EPA Substance Registry System: 2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(517920-59-1)

Safety Data

• Hazardous Substances Data: 517920-59-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is used as a reagent in organic synthesis for its ability to undergo Suzuki-Miyaura coupling reactions, which are crucial for creating carbon-carbon bonds in organic molecules. This property is essential for the development of complex organic structures.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is used as a building block for the creation of complex organic molecules with specific pharmaceutical or biological activities. Its unique structure and reactivity contribute to the design and synthesis of new drug candidates.
Used in Chemical Transformations:
2-[(3-chlorophenyl)Methyl]-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is utilized as a versatile reagent in various chemical transformations due to the stability of the dioxaborolane moiety. This makes it a useful tool in the synthesis of a wide range of organic compounds.

Upstream product

• 108-41-8 1-chloro-3-methylbenzene 
• 73183-34-3 bis(pinacol)diborane 
• 745783-95-3 tert-butyldimethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 1075719-92-4 n-Bu₃SiB(pinacolate) 
• 766-80-3 1-bromomethyl-3-chlorobenzene 
• 86364-03-6 3-chloro-1-trifluoromethanesulfonyloxybenzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 19350-69-7 4-chlorobenzaldehyde p-toluenesulfonylhydrazone 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 587-04-2 m-Chlorobenzaldehyde 
• 622-98-0 4-chloro(ethylbenzene) 
• 56960-97-5 1,2-bis(4-chlorophenyl)ethan-1-ol 
• 1878-66-6 4-chlorophenylacetic Acid 
• 1373432-90-6 C₂₇H₂₈ClN₃O₃ 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1422539-21-6 2,2,6,6-tetramethyl-1-[(4-chlorophenyl)methoxy]piperidine 

Relevant articles and documents

Stereoselective gem-C,B-Glycosylation via 1,2-Boronate Migration

A novel protocol is established for the long-standing challenge of stereoselective geminal bisglycosylations of saccharides. The merger of PPh3 as a traceless glycosidic leaving group and 1,2-boronate migration enables the simultaneous introduction of C-C and C-B bonds at the anomeric stereogenic center of furanoses and pyranoses. The power of this method is showcased by a set of site-selective modifications of glycosylation products for the construction of bioactive conjugates and skeletons. A scarce metal-free 1,1-difunctionalization process of alkenes is also concomitantly demonstrated.

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radica

Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)

Proteasomes are broadly expressed key components of the ubiquitin-dependent protein degradation pathway containing catalytically active subunits (β1, β2, and β5). LMP7 (β5i) is a subunit of the immunoproteasome, an inducible isoform that is predominantly expressed in hematopoietic cells. Clinically effective pan-proteasome inhibitors for the treatment of multiple myeloma (MM) nonselectively target LMP7 and other subunits of the constitutive proteasome and immunoproteasome with comparable potency, which can limit the therapeutic applicability of these drugs. Here, we describe the discovery and structure-based hit optimization of novel amido boronic acids, which selectively inhibit LMP7 while sparing all other subunits. The exploitation of structural differences between the proteasome subunits culminated in the identification of the highly potent, exquisitely selective, and orally available LMP7 inhibitor 50 (M3258). Based on the strong antitumor activity observed with M3258 in MM models and a favorable preclinical data package, a phase I clinical trial was initiated in relapsed/refractory MM patients.

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.

Regioselective α-benzylation of 3-iodoazetidine via Suzuki cross-coupling

An efficient protocol for the synthesis of α-benzyl azetidines starting from benzylboronic acid pinacol ester derivatives and 3-iodoazetidine was developed. A wide range of α-benzyl azetidine derivatives were obtained in moderate to good yields with high regioselectivity (>99%).

Isoquinolone compound and application thereof

The invention relates to an isoquinolone compound and application thereof. The invention in particular relates to an isoquinolone compound used as a HIF prolyl hydroxylase inhibitor (HIF-PHI) and a pharmaceutical composition thereof. Moreover, the present invention provides the application of the isoquinolinone compound or the pharmaceutical composition thereof in the preparation of a medicament for preventing or treating HIF-associated or HIF-mediated diseases as anemia or ischemia, local ischemia or hypoxia.

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.

Method for synthesizing alkylborate compound

The invention discloses a method for synthesizing an alkylborate compound, and concretely relates to a method for synthesizing the alkylborate compound through a cross-coupling reaction of chloralkaneand bis(pinacolato)diboron in the presence of metallic magnesium with Fe(acac)3 (acac = an acetylacetonate group) as a single component catalyst. The method for synthesizing the alkylborate compoundavoids the use of sensitive metal organic solvents and multi-component catalysts, realizes bilateral utilization of the bis(pinacolato)diboron, greatly reduces the use amount of the bis(pinacolato)diboron, and allows the coupling reaction of the cheap and easily-available chloralkane to be smoothly carried out under mild conditions; and compared with methods reported in literatures, the method disclosed in the invention has a better atom economy, a same or higher catalysis efficiency and a wider substrate applicability.