3-Aminobenzeneboronic acid hemisulfate salt Chemical Properties

Melting point:

≥300 °C

storage temp. 

Inert atmosphere,2-8°C

Water Solubility 

Soluble in water

form 

Crystalline Powder

color 

White to slightly beige

Sensitive 

Hygroscopic

BRN 

8094151

InChIKey

XMVGYYBQCXVVHU-UHFFFAOYSA-N

CAS DataBase Reference

66472-86-4

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

3-10

HazardClass 

IRRITANT

HS Code 

29310095

MSDS

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3-Aminobenzeneboronic acid hemisulfate salt Usage And Synthesis

Chemical Properties

White to slightly beige crystalline powder

Uses

3-Aminobenzeneboronic acid hemisulfate salt is a boronic acid derivative, which can be used as an intermediate in pharmaceutical synthesis. Adsorbent additive for the chromatographic separation of 3'-terminal polynucleotides from RNA.

Application

3-Aminophenylboronic acid hemisulfate salt is used in the synthesis of:
Phenylboronic acid-functionalized inverse opal hydrogels within microfluidic flow cells for glucose sensing.
Phenylboronic acid-salicylhydroxamic acid-derived complexing reagent for protein immobilization on chromatographic support.
It can also be used in the preparation of phenylboronic acid (PBA) monolayer-modified Au electrode for the voltammetric sensing of uridine and cytidine.

Preparation

3-Aminobenzeneboronic acid hemisulfate salt synthesis: Benzenamine, 3-bromo-N-(diphenylmethylene)- (80,0 g; 0.24 moles) was added to the cryogenic reactor along with 1.4 equivalents of triisopropyl borate and dissolved in tetrahydrofuran. The resulting solution was cooled to -80°C under an inert atmosphere and 1.35 equivalents of n-butyllithium (as a solution in n-hexane) was added maintaining the internal temperature. When complete conversion was achieved, the reaction mixture was added to a dilute mixture of sulfuric acid (1 M) and toluene. The layers were separated to obtain an aqueous solution of 3-aminophenylboronic acid hydrogen sulfate (assay yield: 85%). 3-Aminobenzeneboronic acid hemisulfate salt can be obtained by precipitating a 0.5 M aqueous solution at pH 7.2 (pH corrected with 33% aqueous NaOH) at a temperature of 0-5°C. Filtration and drying under vacuum at 40°C for 8 hours yielded 21.7 g of 3-Aminobenzeneboronic acid hemisulfate salt (0.16 moles; 66% molar yield).

3-Aminobenzeneboronic acid hemisulfate salt(66472-86-4)Related Product Information

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