4-(2-Tetrahydropyranyloxy)phenylboronic acid Chemical Properties

Melting point:

117-124 °C

Boiling point:

411.3±55.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

8.63±0.16(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C11H15BO4/c13-12(14)9-4-6-10(7-5-9)16-11-3-1-2-8-15-11/h4-7,11,13-14H,1-3,8H2

InChIKey

DMGMCZRNMYQQQB-UHFFFAOYSA-N

SMILES

B(C1=CC=C(OC2OCCCC2)C=C1)(O)O

CAS DataBase Reference

182281-01-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22-36/38

Safety Statements 

36/37/39-26-37/39-36

HazardClass 

IRRITANT

HS Code 

29329990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-(2-Tetrahydropyranyloxy)phenylboronic acid Usage And Synthesis

Chemical Properties

off-white to beige crystalline powder

Uses

suzuki reaction

Uses

[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.

Synthesis

The general procedure for the synthesis of 4-(2'-tetrahydrophenoxy)phenylboronic acid from 2-(4-bromophenoxy)tetrahydro-2H-pyran, triethyl borate, and water (electrophoretic grade) was as follows: tetrahydrofuran (THF, 10 mL) was added to a reaction flask containing magnesium powder (24.3 g, 97.2 mmol) and a small amount of iodine crystals and stirred at room temperature for 1 minutes. Subsequently, a THF solution (40.0 mL) of 2-(4-bromophenoxy)tetrahydro-2H-pyran (25.0 g, 97.2 mmol) was slowly added and stirred for 5 min at room temperature under nitrogen protection, then refluxed for 2 hours. After the reaction was completed, it was cooled to room temperature to obtain the Grignard reagent solution. In another four-necked flask, triethyl borate (31.3 g, 292 mmol) and THF (600 mL) were added and cooled to -15 °C after nitrogen displacement. The Grignard reagent solution was cooled to 0 °C and slowly added dropwise to the THF solution of triethyl borate through a cannula over 30 min. After the dropwise addition was completed, the reaction was continued at 0 °C for 1 h. Gray solid precipitation was observed. 10% aqueous ammonium chloride solution (150 mL) was added to the reaction mixture and stirred at room temperature for 16 hours. The organic layer was extracted by adding ethyl acetate (200 mL), washed sequentially with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration to remove the desiccant, the solvent was removed by distillation under reduced pressure to give a pink solid. Recrystallization with a solvent mixture of ethyl acetate and hexane (1:10, v/v) afforded 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (18.3 g, 83% yield) as a white solid.

References

[1] Patent: JP5761428, 2015, B2. Location in patent: Paragraph 0110-0112

4-(2-Tetrahydropyranyloxy)phenylboronic acid(182281-01-2)Related Product Information

• Anisole
• 2-Phenoxyethanol
• p-Anisaldehyde
• Triclosan
• Diphenyl ether
• Difenoconazole
• Tetrahydropyran
• Tetrahydro-4H-pyran-4-one
• 4-Methoxybenzyl cyanide
• 3-Methoxyacetophenone
• Phenylboronic acid
• (Trifluoromethoxy)benzene
• 4-Propoxyphenylboronic acid
• 4-Butoxyphenylboronic Acid
• 2-ETHOXYPHENYLBORONIC ACID
• 4-(METHOXYMETHYL)PHENYLBORONIC ACID
• Sodium borohydride
• 4-(Ethoxymethoxy)phenylboronic acid