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HomeProduct name list3-Aminobenzeneboronic acid hemisulfate salt

3-Aminobenzeneboronic acid hemisulfate salt

Synonym(s):(m-Aminophenyl)boronic acid hemisulfate;(3-Aminophenyl)boric acid hemisulfate;(3-aminophenyl)-boronic acid sulfate (2:1);3-Aminobenzeneboronic acid hemisulfate salt;Bis[3-dihydroxyboranyl)benzenaminium] sulfate

  • CAS NO.:66472-86-4
  • Empirical Formula: C12H18B2N2O8S
  • Molecular Weight: 371.96692
  • MDL number: MFCD00013111
  • EINECS: 266-376-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-23 13:52:06
3-Aminobenzeneboronic acid hemisulfate salt Structural

What is 3-Aminobenzeneboronic acid hemisulfate salt?

Chemical properties

White to slightly beige crystalline powder

The Uses of 3-Aminobenzeneboronic acid hemisulfate salt

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.

What are the applications of 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).

Properties of 3-Aminobenzeneboronic acid hemisulfate salt

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
CAS DataBase Reference 66472-86-4

Safety information for 3-Aminobenzeneboronic acid hemisulfate salt

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 3-Aminobenzeneboronic acid hemisulfate salt

InChIKey XMVGYYBQCXVVHU-UHFFFAOYSA-N

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