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178756

Sigma-Aldrich

Diphenyl phosphoryl azide

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
Beilstein:
2058967
EC Number:
247-644-0
MDL number:
MFCD00001987
UNSPSC Code:
12352302
PubChem Substance ID:
24850766
NACRES:
NA.22
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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

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Application

Hydroazidation Catalyst for Facile Preparation of Organoazides

Reagent for synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtis rearrangement[1]
Aziridination of olefins catalyzed by colbalt-tetraphenylporphyrin.[2]
Used as the activating agent in the preparation of macrocyclic lactams[3] and of an aldose reductase inhibitor.[4]

Pictograms

Skull and crossbones
GHS06

Signal Word

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX1311
MKCV6744
MKCS7146
MKCJ1322
MKCG7023

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The Journal of Organic Chemistry, 71, 6665-6665 (2006)
Tetrahedron Letters, 31, 6469-6469 (1990)
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
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.
E Benqué et al.
Journal of clinical periodontology, 24(8), 550-556 (1997-08-01)
This study, confined to non-smokers, evaluated guided-tissue regeneration in deep 2-wall intrabony defects using a diphenylphosphorylazide-cross-linked bovine type I collagen membrane supported by a hydroxyapatite/collagen/chondroitin-sulfate spacer in 43 adult periodontitis (AP) and 14 rapidly progressive periodontitis (RPP) patients, no more
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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