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Diphenylphosphoryl Azide
(CAS RN:26386-88-9 Product Number:D1672)

Structure

Diphenylphosphoryl Azide
Synonym DPPA

General Information

Product Number D1672

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Purity/Analysis Method >97.0%(GC)
Storage Temperature 0-10°C
M.F. / M.W. C12H10N3O3P=275.20
CAS RN 26386-88-9
Related CAS RN
MDL Number MFCD00001987
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Appearance Colorless to Almost colorless clear liquid
Purity(GC) min. 97.0 %

References

Reaxys-RN 2058967
PubChem SID 87568148
F&F 8,211
EC Number 247-644-0

GHS

Pictogram
Signal Word Danger
Hazard Statements
  • H300+H310+H330
  • :Fatal by inhalation, in contact with skin and if swallowed.
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P260
  • :Do not breathe mist, vapours or spray.
  • P284
  • :Wear respiratory protection.
  • P301+P310+P330
  • :IF SWALLOWED: Immediately call a POISON CENTER or doctor. Rinse mouth.
  • P302+P352+P310+P361+P364
  • :IF ON SKIN: Wash with plenty of soap and water. Immediately call a POISON CENTER or doctor. Take off immediately all contaminated clothing and wash it before reuse.
  • P304+P340+P310
  • :IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER or doctor.
  • 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.

Transport Information

UN Number 3278
Class 6.1
Packing Group II
HS Number 2929900090

Application

Phosphoryl Azide for Nosylation via Azidation

References

Phosphoryl Azide for Azidations

References

Condensing Agent

Experimental procedure2): To an ice-cooled mixture containing 1 (2.5 mmol) and 2 (2.5 mmol) in dry DMF (15 mL), DPPA (3.0 mmol) is slowly added, followed by drop-wise addition of Et3N (6.3 mmol). The reaction mixture is kept at 0 °C for another 2 h, and then allowed to warm up to room temperature. After 24 h, the reaction mixture is diluted with EtOAc (80 mL) and washed with an aqueous solution of citric acid (10%, 50 mL), H2O (50 mL), saturated aqueous NaHCO3 (50 mL), H2O (50 mL), and brine (50 mL). The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue is purified by column chromatography to afford 3 (83% yield).

References

DPPA: A Stable and Easy-to-handle Azidating Agent

Experimental procedure2): Diphenylphosphoryl azide (0.87 mL, 4.04 mmol) is added to a solution of alcohol 1 (98 mg, 0.40 mmol), PPh3 (211 mg, 0.81 mmol) and DEAD (0.37 mL, 40% in toluene, 0.81 mmol) in THF (5 mL) and the reaction is stirred at room temperature for 24 h. Concentration in vacuo and purification by column chromatography (Et2O:hexanes = 1:9) gave 2 (108 mg, 0.40 mmol, 99%) as a colorless oil.

References

PubMed Literature

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