3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Base Information

• Chemical Name: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester
• CAS No.: 287944-16-5
• Molecular Formula: C11H19BO3
• Molecular Weight: 210.081
• Hs Code.: 29349990
• European Community (EC) Number: 683-692-2
• DSSTox Substance ID: DTXSID50459069
• Nikkaji Number: J1.414.672E
• Wikidata: Q72466008
• Pharos Ligand ID: WHW5MGTMTNT1
• ChEMBL ID: CHEMBL3942505
• Mol file: 287944-16-5.mol

Synonyms:2-(3,6-Dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran;

Chemical Property of 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 0.065mmHg at 25°C
• Melting Point: 63-67℃
• Refractive Index: 1.464
• Boiling Point: 238.637 °C at 760 mmHg
• Flash Point: 98.124 °C
• PSA: 27.69000
• Density: 1.011 g/cm³
• LogP: 1.96450
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 210.1427246
• Heavy Atom Count: 15
• Complexity: 268

Purity/Quality:

97% ^*data from raw suppliers

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 20-35

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCOCC2
• Uses: It plays an important role as intermediate for organic synthesis agrochemical, pharmaceutical and dyestuff field. 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.

Technology Process of 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

There total 14 articles about 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-(3-allyloxy-1-methylene-propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1295521-64-0) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (287944-16-5)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 16h;

Reference yield: 83.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-iodo-3,6-dihydro-2H-pyran → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (287944-16-5)

Guidance literature:

4-iodo-3,6-dihydro-2H-pyran; With isopropylmagnesium bromide; In tetrahydrofuran; at -10 ℃; for 10h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at 20 - 40 ℃; for 4h;

Reference yield: 81.0%

bis(pinacol)diborane (73183-34-3) + 5,6-dihydro-4-trifluoromethylsulfonyloxy-2H-pyran (188975-30-6) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (287944-16-5)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃;

upstream raw materials:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

5,6-dihydro-4-trifluoromethylsulfonyloxy-2H-pyran

bis(pinacol)diborane

Tetrahydro-4H-pyran-4-one

Downstream raw materials:

1-[3-(3,6-Dihydro-2H-pyran-4-yl)-4-nitro-phenyl]-4-methyl-piperazine

methyl N-(tert-butoxycarbonyl)-4-(3,6-dihydro-2H-pyran-4-yl)-L-phenylalaninate

3-(3,6-dihydro-2H-pyran-4-yl)-5-nitro-1-trityl-1H-indazole

(1H-benzo[d]imidazol-2-yl)(4-(3-propoxypyrazin-2-yloxy)phenyl)methanone