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4-(Dimethylamino)pyridine N-Oxide Hydrate
(CAS RN:1005-31-8 Product Number:D3220)

Structure

4-(Dimethylamino)pyridine N-Oxide
Synonym DMAPO Hydrate

General Information

Product Number D3220

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Purity/Analysis Method >98.0%(T)
Storage Temperature
M.F. / M.W. C7H10N2O·xH2O=138.17(as Anhydrous)
CAS RN 1005-31-8
Related CAS RN
MDL Number
Packaging and Container
  • Product Details
  • Safety & Regulations
  • Reference & Application

Specification

Purity(Nonaqueous Titration) min. 98.0 %(calcd.on anh.substance)
Water max. 20.0 %

Data of Reference

mp 97°C(lit.)

References

Beilstein 22(5)9,114
Reaxys-RN 3572
PubChem SID 87558182

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :If on skin: Wash with plenty of soap and water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Application

An Effective Amide Synthesis Using Boronic Acid–DMAPO Cooperative Catalysis

B1886 & D3220

Typical procedure (R1=PhEtCH, R2=Bn, R3=H): A 10 mL flask is charged with 2-phenylbutyric acid (82.1 mg, 0.5 mmol), 3,5-bis(trifluoromethyl)phenylboronic acid (6.5 mg, 5 mol%), and DMAPO hydrate (3.5 mg as anhydrous, 5 mol%) in fluorobenzene (0.2 M). After the mixture is stirred at ambient temperature for 5 min, benzylamine (53.6 mg, 0.5 mmol) is added. The resulting mixture is heated under azeotropic reflux conditions with the removal of water for 17 hours. After the reaction mixture is cooled to ambient temperature, the solvent is evaporated. The residue is purified by column chromatography on silica gel (eluent: hexane:EtOAc=4:1) to give N-benzyl-2-phenylbutanamide as a white solid (125.4 mg, 99% yield).

References

PubMed Literature

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