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Sigma-Aldrich

2-(Bromomethyl)phenylboronic acid

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Synonym(s):
α-Bromo-o-tolueneboronic acid, o-Boronobenzyl bromide
Empirical Formula (Hill Notation):
C7H8BBrO2
CAS Number:
Molecular Weight:
214.85
MDL number:
PubChem Substance ID:
NACRES:
NA.22

mp

158-162 °C

storage temp.

2-8°C

SMILES string

OB(O)c1ccccc1CBr

InChI

1S/C7H8BBrO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H,5H2

InChI key

MYVJCOQGXCONPE-UHFFFAOYSA-N

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This Item
679437684589680516
storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

General description

May contain varying amounts of anhydride.

Application

2-(Bromomethyl)phenylboronic acid can be used as a reactant to synthesize:
  • Boronic acid-functionalized benzyl viologen (o-BBV) from 4,4′-bipyridine. o-BBV finds its application as a chemosensor to sense glucose in aqueous water.
  • 2-(azidomethyl)phenylboronic acid, which is further employed in the preparation of isoquinoline derivatives.
  • Aryl boronic acid derivatives as fluorescent probe for hydrogen peroxide detection.

Reactant involved in:
  • Studies of carbon-boron bond cleavage of phenylboronate-pendant cyclen
  • Development of a sensory system to detect glucose or other monosaccharides and hydroxycarboxylates
  • Synthesis of boronated triaryl and tetraaryl phosphonium salts used in cytotoxicity studies
  • Colorimetry and fluorometry mercury determination with chemosensors composed of rhodamine and boronic acid groups
  • Synthesis of imidazolium-containing boronic acids used as fluoride ion sensors
  • Reactions with adenine for molecules with antiinflammatory antitumor activities 

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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393622

p-Tolylboronic acid

A highly sensitive water-soluble system to sense glucose in aqueous solution
Feng L, et al.
Organic & Biomolecular Chemistry, 9(8), 2938-2942 (2011)
2-(Azidomethyl) phenylboronic acid in the synthesis of isoquinoline derivatives
Ganina OG, et al.
Russian Chemical Bulletin, 54(7), 1606-1611 (2005)
A simple boronic acid-based fluorescent probe for selective detection of hydrogen peroxide in solutions and living cells
Han J, et al.
Bioorganic Chemistry, 81(7), 362-366 (2018)

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