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
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) |
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 |
Abamectin manufacturer
JSK Chemicals
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