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178756

Sigma-Aldrich

Diphenyl phosphoryl azide

97%

Sinônimo(s):

DPPA, Phosphoric acid diphenyl ester azide

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About This Item

Fórmula linear:
(C6H5O)2P(O)N3
Número CAS:
26386-88-9
Peso molecular:
275.20
Beilstein:
2058967
Número CE:
247-644-0
Número MDL:
MFCD00001987
Código UNSPSC:
12352302
ID de substância PubChem:
24850766
NACRES:
NA.22

Nível de qualidade

200

Ensaio

97%

Formulário

liquid

adequação da reação

reaction type: click chemistry

índice de refração

n20/D 1.551 (lit.)

p.e.

157 °C/0.17 mmHg (lit.)

densidade

1.277 g/mL at 25 °C (lit.)

grupo funcional

azide

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

[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

chave InChI

SORGEQQSQGNZFI-UHFFFAOYSA-N

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Aplicação

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.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

233.6 °F - closed cup

Ponto de fulgor (°C)

112 °C - closed cup

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
MKCJ1322
MKCG7023
MKCF8399
MKBZ0923V
MKBW9677V

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Sigma-Aldrich

T84409

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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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Artigos

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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