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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)
B L Mylari et al.
Journal of medicinal chemistry, 34(3), 1011-1018 (1991-03-01)
Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate (1, EBPC) is a potent and specific inhibitor of aldose reductase. It was greater than 4000X more potent in its inhibition of rat lens aldose reductase than the closely related rat or pig kidney aldehyde reductase, thus making
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
P Calero et al.
Biomaterials, 23(16), 3473-3478 (2002-07-09)
Chemical modification of pericardium-based cardiac valves tends to reduce the relatively high degree of biodegradation and calcification of the implanted bioprostheses. We analysed the tissue properties of pericardium from young calves and pigs after crosslinking with different agents (glutaraldehyde. diphenylphosphorylazide

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