4-(Bromomethyl)benzeneboronic acid pinacol ester Chemical Properties

Melting point:

85-89 °C

Boiling point:

351.2±25.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

powder

color 

white to off-white

BRN 

7921808

InChI

InChI=1S/C13H18BBrO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-8H,9H2,1-4H3

InChIKey

CBUOGMOTDGNEAW-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1C1=CC=C(CBr)C=C1

CAS DataBase Reference

138500-85-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-34

Safety Statements 

26-36/37/39-45

RIDADR 

3261

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

TSCA 

No

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

III

HS Code 

29349990

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:ALFA

4-(Bromomethyl)benzeneboronic acid pinacol ester Usage And Synthesis

Description

4-(Bromomethyl)benzeneboronic acid pinacol ester can be used as an active oxygen source in biological assays, such as functional assays, because it generates reactive oxygen species and can act as a fluorescence probe for detection of biological samples.

Chemical Properties

White powder

Uses

4-(Bromomethyl)benzeneboronic acid pinacol ester is used in the synthesis of metalloproteinase-13 inhibitors in the treatment of osteoarthritis.

Synthesis

Pinacol p-tolueneborate (10.91g, 50.0mmol), bromosuccinimide (NBS, 9.91g, 55.0mmol), and azobisisobutyronitrile (AIBN, 0.44g, 2.0mmol) were dissolved in dry of carbon tetrachloride (CCl4, 200 mL), stirred at reflux for 14 hours. The mixture was filtered, the solvent was evaporated, and the mixture was dissolved in ethyl acetate (200 mL). Wash once with distilled water (100 mL) and saturated sodium chloride aqueous solution (100 mL), dry with anhydrous sodium sulfate, and rotary evaporate. Finally, use petroleum ether as the eluent for column chromatography separation to obtain 4-(Bromomethyl)benzeneboronic acid pinacol ester (11.30g, yield 76.1%).

References

[1] Patent: WO2013/25885, 2013, A1. Location in patent: Paragraph 0086
[2] Synthetic Communications, 2002, vol. 32, # 17, p. 2669 - 2676
[3] Patent: EP2450354, 2012, A1

4-(Bromomethyl)benzeneboronic acid pinacol ester(138500-85-3)Related Product Information

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