287944-16-5

Basic information

• Product Name: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester
• Synonyms: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester;2H-Pyran, 3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyran, 95%;3,6-Dihydro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran;2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;3,6-Dihydro-2H-pyran-4-bo...;3,6-Dihydro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;3,6-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran, 2-(3,6-Dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 287944-16-5
• Molecular Formula: C₁₁H₁₉BO₃
• Molecular Weight: 210.08
• Product Categories: Organoborons;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents;Organic boronic acid
• Mol File: 287944-16-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 63-67℃
• Boiling Point: 238.637 °C at 760 mmHg
• Flash Point: 98.124 °C
• Appearance: White to off-white/Solid
• Density: 1.011 g/cm³
• Vapor Pressure: 0.065mmHg at 25°C
• Refractive Index: 1.464
• Storage Temp.: 2-8°C
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester(287944-16-5)
• EPA Substance Registry System: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester(287944-16-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 20-35
• WGK Germany: 3
• Hazardous Substances Data: 287944-16-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 287944-16-5 differently. You can refer to the following data:
1. It plays an important role as intermediate for organic synthesis agrochemical, pharmaceutical and dyestuff field.
2. 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester can be used:To prepare 1,2-dihydro-2-oxopyridine based endocannabinoid system (ECS) modulators.As an intermediate in the synthesis of embryonic ectoderm development (EED) inhibitors.To prepare pyrrolotriazine based IRAK4 inhibitors.

InChI:InChI=1/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-5-7-13-8-6-9/h5H,6-8H2,1-4H3

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 24265-23-4 tetrahydropyran-4-enyl bromide 
• 207611-87-8 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-43-7 Trimethyl borate 
• 141534-86-3 (dihydro-2H-pyran-4(3H)-ylidene)hydrazine 
• 73183-34-3 bis(pinacol)diborane 
• 1295521-64-0 2-(3-allyloxy-1-methylene-propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 75405-45-7 4-(prop-2-en-1-yloxy)but-1-yne 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 188975-30-6 5,6-dihydro-4-trifluoromethylsulfonyloxy-2H-pyran 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 

Downstream Products

• 938197-46-7 methyl N-(tert-butoxycarbonyl)-4-(3,6-dihydro-2H-pyran-4-yl)-L-phenylalaninate 
• 1231926-02-5 4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline 
• 1231925-91-9 N-(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)-3-methylpyridin-2-amine 
• 1231926-00-3 N-(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)phenyl)-3-fluoropyridin-2-amine 
• 1295521-50-4 4-(1-(2-pyrrolidin-1-yl-ethyl)-4-(tetrahydro-pyran-4-yl)-1H-imidazol-2-yl)-piperidine 
• 1002127-60-7 (3,6-dihydro-2H-pyran-4-yl)boronic acid 
• 1448718-20-4 2-benzyloxymethyl-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one 
• 1448718-27-1 2-(1-benzyloxy-ethyl)-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one 
• 1448717-75-6 2-(1-benzyl-4-methyl-pyrrolidin-3-yl)-7-(3,6-dihydro-2H-pyran-4-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one 
• 1450019-80-3 5-(2-(4-fluorophenyl)-5-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-4-yl)-3-methoxypyridin-2-amine trifluoroacertate 
• 1174324-82-3 (+/-)-6-(3-bromophenyl)-3,7-dioxa-bicyclo[4.1.0]heptane 
• 1262037-84-2 4-(3-bromo-4-fluorophenyl)-3,6-dihydro-2H-pyran 
• 1174324-81-2 4-(3-bromophenyl)-3,6-dihydro-2H-pyran 
• 1552287-74-7 C₂₄H₂₃N₅O 

Relevant articles and documents

New synthesis process of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester

The invention relates to a new synthesis process of 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester( as shown in the formula I). The new synthesis process comprises the following steps that (1) tetrahydropyranone (as shown in the formula II) is condensed with hydrazine hydrate to generate a product, namely hydrazone (as shown in the formula III); (2) under alkaline conditions, the hydrazone (asshown in the formula III) reacts with iodine to generate a compound 4-iodo-3,6-dihydro-2H-pyran (as shown in the formula IV); (3) the compound IV and a Grignard reagent are in a Grignard exchange reaction, and then coupled with isopropoxyboronic acid pinacol ester (as shown in the formula V) to prepare a target product, namely the 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester. The synthesis process disclosed by the invention is high in yield, mild in reaction conditions, and suitable for large-scale industrial production.

Method for synthesizing 3, 6-dihydro-2H-pyrazine (thiazine) furan-4-boric acid ester

The invention discloses a method for synthesizing 3, 6-dihydro-2H-pyrazine (thiazine) furan-4-boric acid ester. According to the method, tetrahydropyrazole (thiazine) furan-4-ketone serves as the raw material, generates hydrazone with p-toluenesulfonhydrazide, then reacts with NBS/organic alkali to generate alkenyl bromide and next forms Grignard reagent with magnesium metal, after the Grignard reagent is formed, boron reagent is added for a reaction, and the 3, 6-dihydro-2H-pyrazine (thiazine) furan-4-boric acid ester is obtained. By means of the method, ultralow temperature, column chromatography and palladium catalyzed coupling in a literature method are avoided, raw materials are easy to obtain, cost is low, conditions are mild, and the method has potential industrial application and amplification prospect.

5-Alkyl-2-urea-Substituted Pyridines: Identification of Efficacious Glucokinase Activators with Improved Properties

Two 1-(4-aryl-5-alkyl-pyridin-2-yl)-3-methylurea glucokinase activators were identified with robust in vivo efficacy. These two compounds possessed higher solubilities than the previously identified triaryl compounds (i.e., AM-2394). Structure-activity re