{[azido(phenoxy)phosphoryl]oxy}benzene

• ChemBase ID: 80572
• Molecular Formular: C12H10N3O3P
• Molecular Mass: 275.199861
• Monoisotopic Mass: 275.04597783
• SMILES: P(=O)(N=[N+]=[N-])(Oc1ccccc1)Oc1ccccc1
• Canonical SMILES: O=P(N=[N+]=[N-])(Oc1ccccc1)Oc1ccccc1
• InChI: InChI=1S/C12H10N3O3P/c13-14-15-19(16,17-11-7-3-1-4-8-11)18-12-9-5-2-6-10-12/h1-10H
• InChIKey: SORGEQQSQGNZFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[azido(phenoxy)phosphoryl]oxy}benzene
• IUPAC Traditional name: {[azido(phenoxy)phosphoryl]oxy}benzene; diphenylphosphoryl azide
• Synonyms: DPPA; Diphenyl phosphorazidate; Diphenyl azidophosphonate; Diphenylphosphoryl azide; {[azido(phenoxy)phosphoryl]oxy}benzene; Diphenylphosphorazidate; Diphenylphosphoryl azide; Diphenylphosphonic azide; Diphenyl phosphoryl azide; Diphenylphosphonic azide; Phosphoric acid diphenyl ester azide; 二苯基磷酰叠氮化物; 叠氮磷酸二苯酯

Database IDs

• CAS Number: 26386-88-9
• EC Number: 247-644-0
• MDL Number: MFCD00001987
• Beilstein Number: 2058967
• PubChem SID: 24886273; 162067692; 24850766; 24887491
• PubChem CID: 123414

CALCULATED PROPERTIES

• Acid pKa: 3.7648344
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.0076976
• LogD (pH = 7.4): 3.0076976
• Log P: 3.1217432
• Molar Refractivity: 69.2642 cm^3
• Polarizability: 26.845385 Å^3
• Polar Surface Area: 64.96 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: slightly yellow
• Boiling Point: 157 °C/0.17 mmHg(lit.); 157°C @ 0.17mm; 161-161°C/0.5mm; 161-162°C/0.5mm
• Flash Point: > 110°C; >110°C; >110°C(230°F); 112 °C; 233.6 °F
• Density: 1.275; 1.277 g/ml; 1.277 g/mL at 25 °C(lit.)
• Refractive Index: 1.552; 1.5520; n20/D 1.551; n20/D 1.551(lit.)
• Hydrophobicity(logP): 4.012

Safety Information

• Storage Condition: 2-8°C, Avoid excess heat
• Storage Warning: Toxic/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Toxic (T)
• UN Number: 2810; 3278; UN3278
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; III
• Australian Hazchem: 2X
• Risk Statements: 23/24/25-32-36/38; 23/24/25-36/37/38; R:25
• Safety Statements: 26-27-36/37/39-45; 26-36/37/39-45; S:28-36/37/39-45-53
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335; H301-H311-H331-H315-H319
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311; P280H-P305+P351+P338-P361-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3278 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC); ≥98.0% (HPLC); 95%; 97%
• Grade: purum; technical
• Linear Formula: (C6H5O)2P(O)N3

DETAILS

MP Biomedicals - 02150980

Reagent for peptide synthesis. Also converts carboxylic acids to urethanes
1 ml = approx. 1.28 g

Sigma Aldrich - 178756

Packaging
5, 25, 100 g in glass bottle
Application
Hydroazidation Catalyst for Facile Preparation of OrganoazidesReagent for synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement1

Sigma Aldrich - 79627

Other Notes
Versatile reagent with unique applications in organic synthesis 1; Efficient cyclodimerization of a tetrapeptide derivative 2; Electrophilic amination reactions 3

REFERENCES

• Pyrrolidine enamines of cyclic ketones undergo 1,3-dipolar cycloaddition followed by rearrangement with loss of N₂ to the ring contracted N-phosphoryl amidine which can be base hydrolyzed (high temperature) to the corresponding acid: Tetrahedron Lett., 4749 (1976); (cyclododecanone to cycloundecanecarboxylic acid): Org. Synth. Coll., 7, 135 (1990).
• Li enolates unsubstituted at the ɑ-position can undergo diazo-transfer reactions to give the diazo carbonyl derivatives. With ɑ-alkyl amides, azide transfer occurs to give 3-amino-2H-azirines: Helv. Chim. Acta, 78, 1983 (1995). Enolates of ɑ-unsubstituted carboxamides, on treatment with the reagent, followed by di-t-butyl dicarbonate, give derivatives ɑ-amino acids: Helv. Chim. Acta, 79, 213 (1996):
  
• Enables decarbonylation reactions of aldehydes to be carried out at ambient temperature with a catalytic amount of Chlorotris(triphenylphosphine)rhodium(I), 10468, by regeneration of the catalyst from an inactive Rh carbonyl complex: J. Org. Chem., 57, 5075 (1992).
• In the presence of an amine, carboxylic acids are converted to acyl azides which undergo a modified Curtius reaction in the presence of an alcohol to give alkyl carbamates directly. With t-butanol, the resulting t-butyl carbamates can readily be converted to the free amines with mild acid. Malonic half-esters, e.g. Ethyl hydrogen malonate, A12627, give ɑ-amino acid derivatives: J. Am. Chem. Soc., 94, 6203 (1972); Chem. Pharm. Bull., 22, 1398 (1974); J. Org. Chem., 49, 185 (1984):
  
• Use of the hindered base 1,8-Bis(dimethylamino)naphthalene, L00313, enables the isocyanate intermediates to be isolated: Synth. Commun., 23, 335 (1993). Application to ɑ?-unsaturated acids provides a useful degradation to aldehydes with one C atom fewer by hydrolysis of the intermediate enamine. See, e.g.: Synth. Commun., 20, 589 (1990).
• N-protected amino acids are converted to acyl azides for use in a low racemization peptide coupling technique: J. Am. Chem. Soc., 94, 6203 (1972); Synthesis, 549 (1974); J. Org. Chem., 44, 3101 (1979); 52, 764 (1987). See Appendix 6. The method is also applicable to the coupling of carboxylic acids with thiols: J. Org. Chem., 39, 3302 (1974); Chem. Pharm. Bull., 25, 2423 (1977). Similarly, macrocyclic lactams have been prepared without high dilution by reaction of diacids with diamines: Tetrahedron Lett., 31, 6469 (1990).
• Under Mitsunobu conditions, converts alcohols directly to alkyl azides: Tetrahedron Lett., 1977 (1977). Alternatively, with 1,8-Diazabicyclo[5.4.0]undec-7-ene, A12449, activated (e.g. benzylic) chiral alcohols have been converted to the azides with inversion in high ee: J. Org. Chem., 58, 5886 (1993); for illustrative example, see: Org. Synth., 75, 31 (1997).
• Stable azide-transfer agent.