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225541

Diisopropyl azodicarboxylate

98%

Synonyme(s) :

DIAD, Diisopropyl azodiformate

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A propos de cet article

Formule linéaire :
(CH3)2CHOOCN=NCOOCH(CH3)2
Numéro CAS:
Poids moléculaire :
202.21
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1912326
Assay:
98%
Form:
liquid
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Quality Segment

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

General description

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

Application

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
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. DIAD is also used as a selective deprotecting agent of N-benzyl groups.

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Cet article
742430
description

98%

description

~0.5 M in dichloromethane, ≥95.0% (HPLC)

assay

98%

assay

≥95.0% (HPLC)

Quality Level

200

Quality Level

100

bp

75 °C/0.25 mmHg (lit.)

bp

-

refractive index

n20/D 1.420 (lit.)

refractive index

-

form

liquid

form

solution

storage temp.

2-8°C

storage temp.

2-8°C


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Pictogrammes

Health hazardExclamation markEnvironment

Mot-clé

Warning

Hazard Classifications

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

Organes cibles

Respiratory system

Classe de stockage

10 - Combustible liquids

Que se passe-t-il ?

WGK 2

Point d'éclair (°F)

222.8 °F

Point d'éclair (°C)

106 °C

EPI (équipement de protection individuelle)

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



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Questions

1–3 of 3 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/418/501/product-dating-information-06-25-mk.pdf

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  2. Does the product contain AcroSeal cap technology?

    1 answer
    1. This product is not packaged using AcroSeal cap technology. The closure is a polypropylene screw cap with a PTFE liner.

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  3. 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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