178756
Diphenyl phosphoryl azide
97%
Synonym(s):
DPPA, Phosphoric acid diphenyl ester azide
About This Item
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![1,8-Diazabicyclo[5.4.0]undec-7-ene 98%](/deepweb/assets/sigmaaldrich/product/structures/120/564/5b373e23-1624-489c-8efb-692de0f96ffb/640/5b373e23-1624-489c-8efb-692de0f96ffb.png)
Quality Level
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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Related Categories
Application
Reagent for synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement
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
wgk_germany
WGK 3
flash_point_f
closed cup
flash_point_c
closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Certificates of Analysis (COA)
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Articles
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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