4-(2-Tetrahydropyranyloxy)phenylboronic acid

Base Information

• Chemical Name: 4-(2-Tetrahydropyranyloxy)phenylboronic acid
• CAS No.: 182281-01-2
• Molecular Formula: C11H15BO4
• Molecular Weight: 222.049
• Hs Code.: 29329990
• European Community (EC) Number: 672-301-0
• DSSTox Substance ID: DTXSID60407551
• Nikkaji Number: J1.910.622E
• Mol file: 182281-01-2.mol

Synonyms:182281-01-2;4-(2-tetrahydropyranyloxy)phenylboronic acid;4-(tetrahydro-2h-pyran-2-yloxy)phenylboronic acid;4-Hydroxyphenylboronic acid THP ether;(4-((Tetrahydro-2H-pyran-2-yl)oxy)phenyl)boronic acid;[4-(oxan-2-yloxy)phenyl]boronic Acid;[4-(Tetrahydro-2H-pyran-2-yloxy)phenyl]boronic acid;4-[(Tetrahydropyran-2-yl)oxy]phenylboronic Acid;MFCD02183525;[4-[(Tetrahydro-2H-pyran-2-yl)oxy]phenyl]boronic acid;Boronic acid, B-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-;Boronic acid, [4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]-;4-(Tetrahydro-pyran-2-yloxy)-phenyl boronic acid;SCHEMBL852465;DTXSID60407551;DMGMCZRNMYQQQB-UHFFFAOYSA-N;AKOS004116356;AKOS016843600;4-Hydroxybenzeneboronic acid-THP ether;AB11502;AM62750;CS-W014728;{4-[(Oxan-2-yl)oxy]phenyl}boronic acid;AS-15076;SY026105;A4033;FT-0605432;T3325;[4-(tetrahydropyran-2-yloxy)phenyl]boronic acid;4-(2-(2H)-tetrahydropyranyloxy)phenylboronic acid;4-(tetrahydro-2H-pyran-2-yloxy)-phenylboronic acid;4-(tetrahydro-2h-pyran-2-yloxy)benzeneboronic acid;4-(tetrahydro-2H-pyran-2-yloxy)phenyl boronic acid;J-011662;(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)boronicacid;4-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic acid, AldrichCPR;4-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic Acid (contains varying amounts of Anhydride);4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid

Chemical Property of 4-(2-Tetrahydropyranyloxy)phenylboronic acid

Chemical Property:

• Appearance/Colour: off-white to beige crystalline powder
• Vapor Pressure: 1.68E-07mmHg at 25°C
• Melting Point: 117-124 °C
• Refractive Index: 1.543
• Boiling Point: 411.3 °C at 760 mmHg
• PKA: 8.63±0.16(Predicted)
• Flash Point: 202.5 °C
• PSA: 58.92000
• Density: 1.21 g/cm³
• LogP: 0.27180
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 222.1063391
• Heavy Atom Count: 16
• Complexity: 204

Purity/Quality:

98% ^*data from raw suppliers

[4-[(Tetrahydro-2H-pyran-2-yl)oxy]phenyl]boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-36/38
• Safety Statements: 36/37/39-26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)OC2CCCCO2)(O)O
• Uses: suzuki reaction [4-[(Tetrahydro-2H-pyran-2-yl)oxy]phenyl]boronic Acid is a reagent in the synthesis diclhoroacetamide analogs displaying high anti-cancer avtivity. Also used in the synthesis of organic semiconductors.

Technology Process of 4-(2-Tetrahydropyranyloxy)phenylboronic acid

There total 12 articles about 4-(2-Tetrahydropyranyloxy)phenylboronic acid 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: 83.0%

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene (36603-49-3) + triethyl borate (150-46-9) + water (7732-18-5) → 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (182281-01-2)

Guidance literature:

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 2h;

triethyl borate; In tetrahydrofuran; at -15 - 0 ℃; Inert atmosphere;

water; With ammonium chloride; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield: 82.0%

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene (36603-49-3) → 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (182281-01-2)

Guidance literature:

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1039/c2jm31367g

Reference yield: 81.0%

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene (36603-49-3) + Triisopropyl borate (5419-55-6) → 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (182281-01-2)

Guidance literature:

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With hydrogenchloride; In water; at 25 ℃;

DOI:10.1039/b9nj00296k

upstream raw materials:

4-(tetrahydropyran-2'-yloxy)-1-bromobenzene

3,4-dihydro-2H-pyran

4-bromo-phenol

Trimethyl borate

Downstream raw materials:

N-(isobutoxycarbonyl)-2-[4-(2H-tetrahydropyran-2-yloxy)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

5-bromo-5'-(4-(OTHP)phenyl)-2,2'-bipyridine