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178756

Sigma-Aldrich

Diphenyl phosphoryl azide

97%

Synonym(s):

DPPA, Phosphoric acid diphenyl ester azide

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About This Item

Linear Formula:
(C6H5O)2P(O)N3
CAS Number:
Molecular Weight:
275.20
Beilstein:
2058967
EC Number:
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.551 (lit.)

bp

157 °C/0.17 mmHg (lit.)

density

1.277 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[N-]=[N+]=NP(=O)(Oc1ccccc1)Oc2ccccc2

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

InChI key

SORGEQQSQGNZFI-UHFFFAOYSA-N

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Application

Hydroazidation Catalyst for Facile Preparation of Organoazides

Reagent for synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement
Aziridination of olefins catalyzed by colbalt-tetraphenylporphyrin.
Used as the activating agent in the preparation of macrocyclic lactams and of an aldose reductase inhibitor.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tetrahedron Letters, 31, 6469-6469 (1990)
The Journal of Organic Chemistry, 71, 6665-6665 (2006)
Marcus Baumann et al.
Organic & biomolecular chemistry, 6(9), 1577-1586 (2008-04-19)
The use of a mesofluidic flow reactor is described for performing Curtius rearrangement reactions of carboxylic acids in the presence of diphenylphosphoryl azide and trapping of the intermediate isocyanates with various nucleophiles.
E Benqué et al.
Journal of clinical periodontology, 24(8), 544-549 (1997-08-01)
This study, confined to non-smokers, evaluated guided tissue regeneration using a diphenylphosphorylazide-cross-linked bovine type I collagen membrane in deep 3-wall intrabony defects in 52 adult periodontitis (AP) and 16-rapidly progressive periodontitis (RPP) patients, previously treated for the acute phase of
S Zahedi et al.
Journal of periodontology, 69(9), 975-981 (1998-10-17)
To retard collagen membrane enzymatic degradation and to increase its mechanical strength, the diphenylphosphorylazide (DPPA) technique has been demonstrated to achieve natural cross-links between peptide chains of collagen without leaving any foreign product in the cross-linked molecule. In the present

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