CAS 2446-83-5|Diisopropyl azodicarboxylate|DIAD|偶氮二甲酸二异丙酯|N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide|Azodicarboxylic acid diisopropyl ester|diisopropyl azodicarboxylate|Di...

General Information

Structure

Molecular Formula

C₈H₁₄N₂O₄

Molecular Mass

202.20776

Exact Mass

202.09535694

Charge

InChI

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

InChIKey

VVWRJUBEIPHGQF-UHFFFAOYSA-N

Canonic Smiles

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

Isomeric Smiles

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.6064495

LogD (pH = 7.4)

1.6064495

Log P

1.6064495

Molar Refractivity

47.3138

Polarizability

18.836767

Polar Surface Area

77.32

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

Diisopropyl azodicarboxylate偶氮二甲酸二异丙酯Diisopropyl azodicarboxylateAzodicarboxylic acid diisopropyl esterDIADDiisopropyl azodiformateDiisopropyl diazene-1,2-dicarboxylateBis(isopropyl) azodicarboxylate 96%Diprop-2-yl diazene-1,2-dicarboxylate

IUPAC name

N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide (E)-N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide

IUPAC Traditional name

diisopropyl azodicarboxylate N-[(isopropoxycarbonyl)imino]isopropoxyformamide

Names and Identifiers

Registration numbers

MDL Number

MFCD00008875

EC Number

219-502-8

Beilstein Number

1912326

PubChem SID

2484727624853505162039282

CAS Number

2446-83-5

Wikipedia Title

Diisopropyl_azodicarboxylate

Chemspider ID

4515532

PubChem CID

5363146

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Diisopropyl_azodicarboxylate

Apollo Scientific

OR0923

Alternative to DEAD

Sigma Aldrich

225541

General description
Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.8
Packaging
25, 100 g in poly bottle
5 g in glass bottle
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

11626

Other Notes
Reagent used in the Mitsunobu reaction, reviews8,9
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

Molecule Details

References

PubChem Literature

From Data Sources

• Alternative to 'DEAD' (Diethyl azodicarboxylate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenylphosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).

• An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO₂ to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh₃, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu₃P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).

• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).

• For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide (E)-N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide

IUPAC Traditional name

diisopropyl azodicarboxylate N-[(isopropoxycarbonyl)imino]isopropoxyformamide

Registration numbers

MDL Number

MFCD00008875

EC Number

219-502-8

Beilstein Number

1912326

PubChem SID

2484727624853505162039282

CAS Number

2446-83-5

Wikipedia Title

Diisopropyl_azodicarboxylate

Chemspider ID

4515532

PubChem CID

5363146

Molecule Details

Wikipedia

Diisopropyl_azodicarboxylate

Apollo Scientific

OR0923

Alternative to DEAD

Sigma Aldrich

225541

11626

References

PubChem Literature

From Data Sources

• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:74363