3-(Hydroxymethyl)phenylboronic acid Chemical Properties

Melting point:

95-99 °C (lit.)

Boiling point:

380.5±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.31±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Soluble in water.

BRN 

8832019

InChI

InChI=1S/C7H9BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,9-11H,5H2

InChIKey

HGTDLKXUWVKLQX-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(CO)=C1)(O)O

CAS DataBase Reference

87199-15-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

3-(Hydroxymethyl)phenylboronic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

suzuki reaction

Uses

Reactant used for copper-mediated trifluoromethylation, copper-catalyzed transformations from arylboronic acids in water, Mitsunobu, Suzuki, and amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate. Reactant involved in the synthesis of biologically active molecules including Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors via Suzuki coupling reactions, HIV protease inhibitors with antiviral activity against drug-resistant viruses, Pyrrole derivatives for use as PDE4B inhibitors.

Synthesis

The general procedure for the synthesis of 3-hydroxymethylphenylboronic acid from triisopropyl borate and ((3-bromobenzyl)oxy)(tert-butyl)dimethylsilane is as follows: Example 3B: Synthesis of 3-(hydroxymethyl)phenylboronic acid Example 3A (150 mg, 0.498 mmol) was dissolved in THF (2.49 mL) and the solution was cooled to -78 °C. Under stirring, n-butyllithium (431.1 μL, 0.647 mmol) was slowly added and stirred continuously for 30 hours at this temperature. Subsequently, triisopropyl borate (231 μL, 0.996 mmol) was added and stirring was continued for 20 minutes. After that, the reaction mixture was slowly warmed up to room temperature and stirring was continued for 2.5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed sequentially with water and brine, then dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting crude product was dissolved in HPLC solvent B (90:10:0.1 MeCN:H2O:TFA) and stirred at room temperature for 1 hour. Afterwards, the solution was concentrated in vacuum and purified by preparative liquid chromatography (using an Axia Luna 5μ C18 30×100 mm column with a 10-minute gradient, 20 to 100% B, A = 10:90:0.1 MeCN:H2O:TFA, B = 90:10:0.1 MeCN:H2O:TFA) to give Example 3B (57 mg, yield 75%). 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm: 7.75 (1H, s), 7.67 (1H, d, J = 7.28 Hz), 7.40-7.48 (1H, m), 7.30-7.40 (1H, m), 4.60 (2H, s).

References

[1] Patent: WO2014/201073, 2014, A1. Location in patent: Paragraph 00214
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 1, p. 67 - 72

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