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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:
26386-88-9
Molecular Weight:
275.20
Beilstein/REAXYS Number:
2058967
EC Number:
247-644-0
MDL number:
MFCD00001987
UNSPSC Code:
12352302
PubChem Substance ID:
24850766
NACRES:
NA.22

Quality Level

200

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
GHS06

signalword

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

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

wgk_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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The Journal of Organic Chemistry, 71, 6665-6665 (2006)
Tetrahedron Letters, 31, 6469-6469 (1990)
Qiaoya Li et al.
European journal of medical research, 22(1), 48-48 (2017-11-23)
This study aimed to investigate the therapeutic effects of 5-fluorouracil (5-FU)-loaded nanobubbles irradiated with low-intensity, low-frequency ultrasound in nude mice with hepatocellular carcinoma (HCC). A transplanted tumor model of HCC in nude mice was established in 40 mice, which were
Kenichi Tanaka et al.
Molecular bioSystems, 4(6), 512-514 (2008-05-22)
A Vaska-type complex carrying a ferrocene-appended diphosphine ligand was developed as a prototype of autonomous molecular machines that is able to undergo continuous scissoring motion in the presence of diphenylphosphoryl azide and aldehyde.
Charles S Zahedi et al.
Journal of periodontology, 74(7), 1071-1079 (2003-08-23)
Several bioabsorbable collagen membranes are either currently available or under investigation for use in guided tissue regeneration (GTR) procedures. The aim of this 12-month reentry study was to evaluate a diphenylphosphorylazide (DPPA)-cross-linked bovine type I collagen membrane in the healing
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Since the preparation of the first organic azide, phenyl azide, by Peter Griess in 1864 this energy-rich and versatile class of compounds has enjoyed considerable interest.

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