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Merck
CN

225541

Diisopropyl azodicarboxylate

98%

Synonym(s):

DIAD, Diisopropyl azodiformate

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About This Item

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

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InChI

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

SMILES string

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

InChI key

VVWRJUBEIPHGQF-MDZDMXLPSA-N

assay

98%

form

liquid

impurities

≤2% dichloromethane

Quality Level

200

bp

75 °C/0.25 mmHg (lit.)

density

1.027 g/mL at 25 °C (lit.)

functional group

azo

storage temp.

2-8°C

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General description

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

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

signalword

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

10 - Combustible liquids

wgk

WGK 2

flash_point_f

222.8 °F

flash_point_c

106 °C

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB0577
MKCX6500
WXBF5713V
MKCW8212
MKCT0602

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Zhi-Huang Qiu et al.
The Annals of thoracic surgery, 110(3), 925-932 (2020-01-29)
The efficacy of hemiarch replacement combined with a modified triple-branched stent graft in Debakey type I aortic dissection remains to be confirmed. From January 2016 to December 2017, 167 patients with acute Debakey type I aortic dissection underwent hemiarch replacement
Improved procedure for the selective N-debenzylation of benzylamines by diisopropyl azodicarboxylate
Kroutil J, et al.
Synthesis, 2004(03), 446-450 (2004)
An investigation of the Mitsunobu reaction in the preparation of peptide oxazolines, thiazolines, and aziridines
Wipf P and Miller CP
Tetrahedron Letters, 33(42), 6267-6270 (1992)
Marcelle L Ferguson et al.
Journal of the American Chemical Society, 128(14), 4576-4577 (2006-04-06)
Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields.
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.
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