Skip to Content
Merck
All Photos(6)

Key Documents

View All Documentation

225541

Sigma-Aldrich

Diisopropyl azodicarboxylate

98%

Synonym(s):

DIAD, Diisopropyl azodiformate

Sign Into View Organizational & Contract Pricing

Select a Size

5 G
$45.40
25 G
$112.00
100 G
$223.00
500 G
$491.00

$45.40

Please contact Customer Service for Availability
Request a Bulk Order
All Photos(6)

Select a Size

Change View
5 G
$45.40
25 G
$112.00
100 G
$223.00
500 G
$491.00

About This Item

Linear Formula:
(CH3)2CHOOCN=NCOOCH(CH3)2
CAS Number:
2446-83-5
Molecular Weight:
202.21
Beilstein:
1912326
MDL number:
MFCD00008875
UNSPSC Code:
12352302
PubChem Substance ID:
24853505
NACRES:
NA.22
form:
liquid
Assay:
98%

$45.40

Please contact Customer Service for Availability
Request a Bulk Order

Quality Level

200

Assay

98%

form

liquid

impurities

≤2% dichloromethane

refractive index

n20/D 1.420 (lit.)

bp

75 °C/0.25 mmHg (lit.)

density

1.027 g/mL at 25 °C (lit.)

functional group

azo

storage temp.

2-8°C

SMILES string

CC(C)OC(=O)\N=N\C(=O)OC(C)C

InChI

1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+

InChI key

VVWRJUBEIPHGQF-MDZDMXLPSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.[1]

Application

Diisopropyl azodicarboxylate (DIAD) is a commonly used reagent in organic synthesis for the preparation of useful chemical intermediates. It is often used in the Mitsunobu and aza-Baylis-Hillman reaction.[2][3] DIAD is also used as a selective deprotecting agent of N-benzyl groups.[4]
Reactant for preparation of:
  • Chromenes resembling classical cannabinoids
  • MK-3281 inhibitor of the hepatitis C virus NS5B polymerase
  • Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)
  • Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties
  • Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells
  • 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists
  • Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine

Signal Word

Warning

Hazard Classifications

Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

222.8 °F

Flash Point(C)

106 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCW8212
MKCT0602
WXBF0542V
MKCR9578
MKCS2774

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Eun-Hye Kim et al.
International journal of molecular sciences, 21(10) (2020-05-28)
Cancer immunotherapy has been revolutionized by the development of monoclonal antibodies (mAbs) that inhibit interactions between immune checkpoint molecules, such as programmed cell-death 1 (PD-1), and its ligand PD-L1. However, mAb-based drugs have some drawbacks, including poor tumor penetration and
Petia Atanasova et al.
Nanomaterials (Basel, Switzerland), 9(5) (2019-05-30)
The robust, anisotropic tobacco mosaic virus (TMV) provides a monodisperse particle size and defined surface chemistry. Owing to these properties, it became an excellent bio-template for the synthesis of diverse nanostructured organic/inorganic functional materials. For selective mineralization of the bio-template
Aza-Baylis-Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile
Shi M and Zhao G-L
Tetrahedron, 60(9), 2083-2089 (2004)
J Miles Blackburn et al.
Organic letters, 19(21), 6012-6015 (2017-10-20)
A general approach to access sulfamate esters through preparation of sulfamic acid salts, subsequent activation with triphenylphosphine ditriflate, and nucleophilic trapping is disclosed. The method proceeds in modest to excellent yields to incorporate nucleophiles derived from aliphatic alcohols and phenols.
Jorge J Llibre-Guerra et al.
JAMA network open, 2(12), e1917126-e1917126 (2019-12-12)
The amyloid/tau/neurodegeneration (A/T/N) framework uses cerebrospinal fluid (CSF) levels of total tau (tTau) as a marker of neurodegeneration and CSF levels of phosphorylated tau 181 (pTau181) as a marker of tau tangles. However, it is unclear whether CSF levels of
View All Related Papers

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

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service