4-Isopropoxylphenylboronic acid Chemical Properties

Melting point:

150-154°C

Boiling point:

321.9±44.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.78±0.17(Predicted)

form 

Powder

color 

White to off-white or light tan

InChI

1S/C9H13BO3/c1-7(2)13-9-5-3-8(4-6-9)10(11)12/h3-7,11-12H,1-2H3

InChIKey

CJUHQADBFQRIMC-UHFFFAOYSA-N

SMILES

CC(C)Oc1ccc(cc1)B(O)O

CAS DataBase Reference

153624-46-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

Storage Class

13 - Non Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

4-Isopropoxylphenylboronic acid Usage And Synthesis

Chemical Properties

White to off-white or light tan powder

Uses

Reactant for:• ;Microwave-mediated click-chemistry synthesis of glyco-porphyrin derivatives with in vitro photo-cytotoxicity for application in photodynamic therapy1• ;Palladium-catalyzed oxidative cross-coupling reactions2• ;Ruthenium-catalyzed hydrogenation reactions3• ;Stereoselective rhodium-catalyzed arylation4• ;Palladium acetate catalyzed C-glycosidation5

Uses

suzuki reaction

Uses

4-Isopropoxyphenylboronic Acid is used to synthesize potent cytotoxic analogues of the marine alkaloid Lamellarin D. It is also used to synthesize cyclooxygenase-2 (COX-2) inhibitors.

General Description

Contains varying amounts of anhydride

Synthesis

A pentane solution of tert-butyllithium (1.28 M, 51.5 mL, 66.0 mmol) was added dropwise to a solution of 4-isopropoxybromobenzene (5.61 g) in THF (150 ) at -78 ??C under an argon atmosphere. mL) to a solution of 4-isopropoxybromobenzene (5.61 g) in THF (150 ). The mixture was stirred for 1 hour. Trimethyl borate (5.02 mL, 45.0 mmol) was was added to the mixture as a pure liquid. Stir the mixture at -78 ??C for 1 hour. Allow the reaction mixture to warm to room temperature. Stir the reaction mixture for another 1 hour. Quench the mixture with saturated NH4Cl Quench the mixture with saturated NH4Cl aqueous solution. Evaporate the mixture under reduced pressure. Adjust the pH of the residue to 3 by adding 3 M aqueous HCl. Extract the mixture with dichloromethane. Wash the extract with brine. Dry the extract with Na2SO4. Na2SO4 to dry the extract. Evaporate the extract under reduced pressure. The residual solid was washed with hexane. Filter the solid to obtain 4-isopropoxyphenylboronic acid.

4-Isopropoxylphenylboronic acid(153624-46-5)Related Product Information

• (Trifluoromethoxy)benzene
• 2-Phenoxyethanol
• p-Anisaldehyde
• 4-Methoxybenzyl cyanide
• Anisole
• 4-Methoxyphenylboronic acid
• Phenylboronic acid
• Titanium tetraisopropanolate
• 3-Methoxyacetophenone
• (4-METHOXYPHENYL)-BORANE
• 4-Methoxybenzoyl chloride
• 2-CHLORO-4-ISOPROPROXYPHENYLBORONIC ACID
• 3,5-DIMETHYL-4-ISOPROPOXYPHENYLBORONIC &
• 4-ISOPROPOXY-3-METHYLPHENYLBORONIC ACID
• 4-ISOPROPOXY-1,3-PHENYLENEBISBORONIC ACID
• 3-FLUORO-4-ISOPROPOXYPHENYLBORONIC ACID
• 3-CHLORO-4-ISOPROPOXYPHENYLBORONIC ACID
• 4-ISOPROPOXY-2-METHYLPHENYLBORONIC ACID