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178756

Sigma-Aldrich

Diphenyl phosphoryl azide

97%

Sinonimo/i:

DPPA, Phosphoric acid diphenyl ester azide

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About This Item

Formula condensata:
(C6H5O)2P(O)N3
Numero CAS:
26386-88-9
Peso molecolare:
275.20
Beilstein:
2058967
Numero CE:
247-644-0
Numero MDL:
MFCD00001987
Codice UNSPSC:
12352302
ID PubChem:
24850766
NACRES:
NA.22

Livello qualitativo

200

Saggio

97%

Forma fisica

liquid

Impiego in reazioni chimiche

reaction type: click chemistry

Indice di rifrazione

n20/D 1.551 (lit.)

P. eboll.

157 °C/0.17 mmHg (lit.)

Densità

1.277 g/mL at 25 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

[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
SORGEQQSQGNZFI-UHFFFAOYSA-N

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Applicazioni

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.

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H301 + H311 + H331,H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

233.6 °F - closed cup

Punto d’infiammabilità (°C)

112 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
MKCJ1322
MKCG7023
MKCF8399
MKBZ0923V
MKBW9677V

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Diphenyl phosphate 99%

Sigma-Aldrich

850608

Diphenyl phosphate

Benzenesulfonyl azide, functionalized silica gel 40-63 μm, extent of labeling: 0.5-1.0 mmol/g loading

Sigma-Aldrich

590274

Benzenesulfonyl azide, functionalized silica gel

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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Articoli

Acid Halogenation Reagents

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.

Hydroazidation Catalyst

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

Organic Azides and Azide Sources

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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