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178756

Diphenyl phosphoryl azide

Name: Diphenyl phosphoryl azide
Brand: ALDRICH

97%

Synonym(s):

DPPA, Phosphoric acid diphenyl ester azide

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About This Item

Linear Formula:

(C₆H₅O)₂P(O)N₃

CAS Number:

26386-88-9

Molecular Weight:

275.20

UNSPSC Code:

12352302

NACRES:

NA.22

PubChem Substance ID:

24850766

EC Number:

247-644-0

Beilstein/REAXYS Number:

2058967

MDL number:

MFCD00001987

Assay:

97%

Form:

liquid

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Quality Level

200

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.)

functional group

azide

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

Related Categories

Azides

Chemical Biology

Click Chemistry Reagents Overview

Application

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.

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331,H315,H319,H335

pcodes

P261 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338

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

Storage Class

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

wgk

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

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

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The Journal of Organic Chemistry, 71, 6665-6665 (2006)

Tetrahedron Letters, 31, 6469-6469 (1990)

Toward autonomously operating molecular machines driven by transition-metal catalyst.

Kenichi Tanaka et al.

Molecular bioSystems, 4(6), 512-514 (2008-05-22)

A Vaska-type complex carrying a ferrocene-appended diphosphine ligand was developed as a prototype of autonomous molecular machines that is able to undergo continuous scissoring motion in the presence of diphenylphosphoryl azide and aldehyde.

Use of diphenylphosphorylazide for cross-linking collagen-based biomaterials.

H Petite et al.

Journal of biomedical materials research, 28(2), 159-165 (1994-02-01)

Cross-linking of collagen-based biomaterials increases their strength and persistence in vivo. Recently, we described an efficient cross-linking process via the formation of acyl azide groups on methylated carboxyl groups of collagen using hydrazine and nitrous acid (referred to here as

Guided tissue regeneration in human Class II furcation defects using a diphenylphosphorylazide-cross-linked collagen membrane: a consecutive case series.

Charles S Zahedi et al.

Journal of periodontology, 74(7), 1071-1079 (2003-08-23)

Several bioabsorbable collagen membranes are either currently available or under investigation for use in guided tissue regeneration (GTR) procedures. The aim of this 12-month reentry study was to evaluate a diphenylphosphorylazide (DPPA)-cross-linked bovine type I collagen membrane in the healing

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Fluoroamidinium salts advance acid halogenation with greater stability and no oxazolones conversion compared to chlorides.

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.

Global Trade Item Number

SKU	GTIN
178756-5G	04061838753946
178756-25G	04061838753939
178756-5KG	04061838125224
178756-100G	04061838753922
178756-500G	04061838134875

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