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4-(Bromomethyl)benzeneboronic acid pinacol ester

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4-(Bromomethyl)benzeneboronic acid pinacol ester Basic information

Product Name:
4-(Bromomethyl)benzeneboronic acid pinacol ester
Synonyms:
  • 4-Bromomethylphenylboronic acid pinacol ester 95%
  • 4-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER
  • 4-BROMOMETHYLPHENYLBORONIC ACID, PINACOL ESTER
  • 4-(Bromomethyl)benzeneboronic acid pinacol cyclic ester
  • 4-(Bromomethyl)phenylboronic acid pinacol cyclic ester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • 4-(Bromomethyl)phenylboronicacidpinacolcyclicester~2-[(4-Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • 2-[(4-bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • 4-(bromomethyl)phenylboronic acid pinacol cyclic ester
CAS:
138500-85-3
MF:
C13H18BBrO2
MW:
297
EINECS:
679-122-7
Product Categories:
  • Boronic acids
  • blocks
  • BoronicAcids
  • Bromides
Mol File:
138500-85-3.mol
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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)
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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

MSDS

  • Language:English Provider:ALFA
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4-(Bromomethyl)benzeneboronic acid pinacol ester Usage And Synthesis

Chemical Properties

White powder

Uses

2-[4-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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%).

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