138500-85-3

Basic information

• Product Name: 4-(Bromomethyl)benzeneboronic acid pinacol ester
• Synonyms: 138500-85-3;4-Bromomethylphenylboronic acid pinacol ester 95%;4-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER;4-BROMOMETHYLPHENYLBORONIC ACID, PINACOL ESTER;4-(Bromomethyl)benzeneboronic acid pinacol cyclic ester;4-(Bromomethyl)phenylboronic acid pinacol cyclic ester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(Bromomethyl)phenylboronicacidpinacolcyclicester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(4-bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 138500-85-3
• Molecular Formula: C₁₃H₁₈BBrO₂
• Molecular Weight: 297
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Bromides;Boronic acids
• Mol File: 138500-85-3.mol

Chemical Properties

• Melting Point: 83-85°C
• Boiling Point: 351.2 °C at 760 mmHg
• Flash Point: 166.2 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 8.44E-05mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: Keep Cold
• Solubility: soluble in Toluene
• BRN: 7921808
• CAS DataBase Reference: 4-(Bromomethyl)benzeneboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Bromomethyl)benzeneboronic acid pinacol ester(138500-85-3)
• EPA Substance Registry System: 4-(Bromomethyl)benzeneboronic acid pinacol ester(138500-85-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 138500-85-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(Bromomethyl)benzeneboronic acid pinacol ester is used as a synthetic intermediate for the development of metalloproteinase-13 inhibitors. These inhibitors are crucial in the treatment of osteoarthritis, a degenerative joint disease that affects millions of people worldwide. The compound plays a significant role in modulating the activity of metalloproteinase-13, which is involved in the breakdown of cartilage in the joints, thus helping to alleviate the symptoms and progression of osteoarthritis.
Used in Organic Chemistry Research:
In addition to its pharmaceutical applications, 4-(Bromomethyl)benzeneboronic acid pinacol ester is also utilized as a versatile reagent in organic chemistry research. Its unique chemical properties allow it to be employed in various chemical reactions, such as cross-coupling reactions, Suzuki-Miyaura reactions, and other C-C bond forming processes. This makes it a valuable tool for the synthesis of complex organic molecules, including potential drug candidates and other bioactive compounds.
Used in Material Science:
The compound's chemical properties also make it suitable for use in material science, where it can be employed in the development of new materials with specific properties. For instance, it can be used to create novel polymers or to modify existing ones, potentially leading to improved performance in various applications, such as coatings, adhesives, or composite materials.

InChI:InChI=1/C13H18BBrO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-8H,9H2,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 68162-47-0 4-bromomethylphenylboronic acid 
• 7789-60-8 phosphorus tribromide 
• 302348-51-2 (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol 
• 488133-21-7 2-(4-(bromomethyl)phenyl)-1,3,2-dioxaborolane 
• 69519-10-4 2-(p-tolyl)-1,3,2-dioxaborolane 
• 873-75-6 4-bromobenzenemethanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 59016-93-2 p-hydroxymethylphenylboronic acid 
• 5720-05-8 4-methylphenylboronic acid 
• 128-08-5 N-Bromosuccinimide 
• 195062-57-8 p-tolylboronic pinacol ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 138500-87-5 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]isoindoline-1,3-dione 
• 854372-33-1 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzylsulfanyl]benzofuran 
• 879487-00-0 4,4,5,5-tetramethyl-2-{4-[(methylthio)methyl]phenyl}-1,3,2-dioxaborolane 
• 1239481-05-0 2-(4-(azidomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1346936-32-0 N,N-bis(2-hydroxyethyl)-N-methyl-N-[4-(6-methyl-1,3,6,2-dioxazaborocan-2-yl)phenyl]methanaminium bromide 
• 1346936-29-5 N,N-bis(2-chloroethyl)-N-methyl-N-(4-boronophenyl)methanaminium bromide 
• 1346936-27-3 N, N-bis(2-chloroethyl)-N-methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] methanaminium bromide 
• 1346936-38-6 [CH₃N(C₂H₄Cl)2CH₂C₆H₄OBO₂C₂(CH₃)4]⁽¹⁺⁾*Br^(1-)=[CH₃N(C₂H₄Cl)2CH₂C₆H₄OBO₂C₂(CH₃)4]Br 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 1346936-33-1 N,N,N-trimethyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanaminium bromide 
• 1260369-06-9 4-[{4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl}(4H-1,2,4-triazol-4-yl)amino]benzonitrile 
• 1414867-90-5 methyl 4-(3-(2-hydroxyphenyl)-5-(2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)phenyl)-1H-1,2,4-triazol-1-yl)benzoate 
• 1437111-22-2 9-nitro-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-3,4,5,6-tetrahydro-2H-imidazo[2,1-b][1,3,6]oxadiazocine 

Relevant articles and documents

Synthesis and Automated Labeling of [18F]Darapladib, a Lp-PLA2 Ligand, as Potential PET Imaging Tool of Atherosclerosis

Atherosclerosis and its associated clinical complications are major health issues in industrialized countries. Lipoprotein-associated phospholipase A2 (Lp-PLA2) was demonstrated to play an important role in atherogenesis and to be a

A Persulfide Donor Responsive to Reactive Oxygen Species: Insights into Reactivity and Therapeutic Potential

Persulfides (RSSH) have been hypothesized as critical components in sulfur-mediated redox cycles and as potential signaling compounds, similar to hydrogen sulfide (H2S). Hindering the study of persulfides is a lack of persulfide-donor compounds

A General Strategy Toward Highly Fluorogenic Bioprobes Emitting across the Visible Spectrum

A general approach toward highly fluorogenic probes across the visible spectrum for various analytes offers significant potential for engineering a wide range of bioprobes with diverse sensing and imaging functions. Here we show a facile and general strategy that involves introducing a new fluorogenic mechanism in boron dipyrromethene (BODIPY) dyes, based on the principle of stimuli-triggered dramatic reduction in the electron-withdrawing capabilities of the meso-substituents of BODIPYs. The fluorogenic mechanism has been demonstrated to be applicable in various BODIPYs with emission maxima ranging from green to far red (509, 585, and 660 nm), and the synthetic strategy allows access to a panel of highly fluorogenic bioprobes for various biomolecules and enzymes (H2O2, H2S, and protease) via introducing specific triggering motifs. The potency of the general design strategy is exemplified by its application to develop a mitochondria-targeting far-red probe capable of imaging of endogenous H2O2 in living cells.

Inhibition of RANTES/CCR1-mediated chemotaxis by cosalane and related compounds

The anti-HIV agent cosalane and several of its analogues inhibited RANTES-induced migration of human monocytes, but they did not inhibit migration induced by MIP1α or MIP1β. RANTES-induced migration of single receptor CCR1-HEK transfectants was also inhib

A Two-Photon Ratiometric Sensing Platform Based on Solid-State Luminescent Benzocoumarin: Application to Prolonged Bioimaging of Hydrogen Peroxide

Fluorescent probes provide essential tools for studying biological systems. For the prolonged imaging of cellular analytes, the fast clearance of small-molecular probes and products is a matter of concern in the quantitative analysis. Activatable probes that produce insoluble products inside cells can be used for prolonged imaging, but those with ratiometric imaging capability are rare. We disclose a novel sensing platform that is capable of prolonged imaging, in addition to ratiometric signaling for reliable quantitative analysis. Specifically, 3-(pyridin-4-yl)-8-(pyrrolidin-1-yl)-2H-benzo[g]chromen-2-one and its pyridinium salt as a product/probe couple constitute the ratiometric sensing platform. As the former dye produces highly emissive insoluble nanoaggregates inside cells, a fluorescent probe in the latter form enables prolonged imaging of the target analyte in cells as well as in tissue by two-photon microscopy.

DRUG AND GENE THERAPY TO TREAT HIGH MYOPIA AND OTHER OCULAR DISORDERS WITH ENLARGED EYE GLOBES

This invention relates to a treatment of various eye conditions relating to eye enlargement. The conditions can be treated by inhibiting an upstream protein within the said biological pathway or by increasing the expression of a downstream receptor within

A synthetic route to 1-(4-boronobenzyl)-1H-pyrrole

The synthesis of 1-(4-boronobenzyl)-1H-pyrrole was investigated using three different routes. Two key routes that involved the introduction of the boronate group protected as the pinacol ester, failed, due to deprotection problems. The route involving the

Thiourea-Mediated Halogenation of Alcohols

The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.

Camptothecin derivative and applications thereof

The invention provides a camptothecin derivative and applications in preparation of antitumor drugs, wherein the camptothecin derivative has the following general formula (I). According to the invention, the MTT experiment results show that the camptothecin derivative has cytotoxicity only under ROS conditions, and has low cytotoxicity in a ROS-free culture solution; and based on high ROS concentration in tumor tissue, the anti-tumor medicine prepared from the camptothecin derivative has the advantage of low toxicity.

RADIOLABELED DARAPLADIB AND ANALOGS THEREOF AND THEIR USE AS IMAGING COMPOUNDS

The present inventors have developed new radiolabeled Darapladib and analogs thereof which can be used for the specific detection of vulnerable atherosclerotic plaques by targeting lipoprotein-associated phospholipase A2 (Lp-PLA2) which is a biomarker of