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679453

Sigma-Aldrich

2-(Bromomethyl)phenylboronic acid

Synonym(s):

α-Bromo-o-tolueneboronic acid, o-Boronobenzyl bromide

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About This Item

Empirical Formula (Hill Notation):
C7H8BBrO2
CAS Number:
91983-14-1
Molecular Weight:
214.85
MDL number:
MFCD01318941
UNSPSC Code:
12352103
PubChem Substance ID:
24885495
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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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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

679453-5G:
679453-BULK:
679453-1G:
679453-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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