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Merck

178756

Sigma-Aldrich

Diphenylphosphorylazid

97%

Synonym(e):

DPPA, Diphenylphosphoryl azid

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About This Item

Lineare Formel:
(C6H5O)2P(O)N3
CAS-Nummer:
Molekulargewicht:
275.20
Beilstein:
2058967
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352302
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

97%

Form

liquid

Eignung der Reaktion

reaction type: click chemistry

Brechungsindex

n20/D 1.551 (lit.)

bp

157 °C/0.17 mmHg (lit.)

Dichte

1.277 g/mL at 25 °C (lit.)

Lagertemp.

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

InChIKey

SORGEQQSQGNZFI-UHFFFAOYSA-N

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Anwendung

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

Piktogramme

Skull and crossbones

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

233.6 °F - closed cup

Flammpunkt (°C)

112 °C - closed cup

Persönliche Schutzausrüstung

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


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Kunden haben sich ebenfalls angesehen

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.
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Tetrahedron Letters, 31, 6469-6469 (1990)

Artikel

The generation of an acid chloride is an obvious way to activate the carboxy group for amide bond formation. However, practical application of acid chlorides in peptide synthesis is restricted, because they are prone to side reactions and racemization.

The chemistry of organoazides is exceedingly rich, since the azide functionality reacts with electrophiles, nucleophiles, and dipolarophiles, with or without the extrusion of dinitrogen. Common place transformation such as Staudinger reductions or ligations, Cu(I)-catalyzed Huisgen cycloadditions (of the “click” reaction family), Curtius or Schmidt rearrangents, nitrene reactions, or imine formation via aza-Wittig reactions all necessitate organoazide precursors or intermediates

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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