178756

Sigma-Aldrich

Diphenyl phosphoryl azide

97%

Synonym(s):
Phosphoric acid diphenyl ester azide, DPPA
Linear Formula:
(C6H5O)2P(O)N3
CAS Number:
Molecular Weight:
275.20
Beilstein/REAXYS Number:
2058967
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

97%

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

Aziridination of olefins catalyzed by colbalt-tetraphenylporphyrin.
Used as the activating agent in the preparation of macrocyclic lactams and of an aldose reductase inhibitor.
Hydroazidation Catalyst for Facile Preparation of Organoazides

Reagent for synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement

Packaging

5, 25, 100, 500 g in glass bottle
5 kg in poly drum

pictograms

Skull and crossbones

signalword

Danger

hazcat

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 Germany

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

Certificate of Analysis

Certificate of Origin

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...
D. Sawada, et al.,
Tetrahedron, 64, 8780-8788 (2008)
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...
Tetrahedron Letters, 31, 6469-6469 (1990)
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