4-(Hydroxymethyl)phenylboronic acid Chemical Properties

Melting point:

251-256 °C (lit.)

Boiling point:

362.0±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

8.53±0.10(Predicted)

color 

White to slightly yellow

PH

4.5 (10g/l, H2O)

Water Solubility 

25 g/L

BRN 

2831413

InChI

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

InChIKey

PZRPBPMLSSNFOM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

59016-93-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

4-(Hydroxymethyl)phenylboronic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

suzuki reaction

Uses

Reactant involved in the synthesis of biologically active compounds including:

• Imidazo[4,5-b]pyrazin-2-ones for use as mTOR kinase inhibitors
• Human immunodificiency virus protease inhibitors with activity against resistant viruses

Reactant involved in:

• Suzuki coupling reactions
• Copper-catalyzed transformation from arylboronic acids in water

Involved in the synthesis of polyurethane containing spindle-type chromophores

Synthesis

Sodium borohydride (0.38 g, 11 mmol) was added to a solution of (4-formylphenyl)boronic acid (1.5 g, 11 mmol) in methanol (40 mL) in batches at 0 °C, keeping the temperature at 0 °C and stirring the reaction mixture for 1 hour. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was dissolved in water, cooled to 0-5 °C, and the pH was adjusted to 5 by slowly adding 5% aqueous acetic acid.The precipitated solid was collected by diafiltration and washed with cold water, and dried to give 4-hydroxymethylphenylboronic acid (1.2 g, 80% yield). The product was characterized by 1H NMR (400 MHz, CD3OD): δ 7.72 (d, J=7.2 Hz, 2H), 7.59 (d, J=7.6 Hz, 2H), 7.35-7.30 (m, 2H), 4.60 (s, 2H); Mass Spectrometry (ES+): m/z 542.15,544.35 [M+H]; LCMS retention time: tR = 2.42 min.

References

[1] Patent: WO2015/81280, 2015, A1. Location in patent: Paragraph 00689; 00698; 00699
[2] Patent: US5827887, 1998, A
[3] Dyes and Pigments, 2012, vol. 92, # 3, p. 982 - 987
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
[5] Patent: US6576789, 2003, B1

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