1,1'-(Azodicarbonyl)-dipiperidine Chemical Properties

Melting point:

132-136 °C(lit.)

Boiling point:

366.4±25.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly), insol petroleum ether; sol ethanol, ether, THF

pka

-0?+-.0.20(Predicted)

form 

solid

color 

yellow

Water Solubility 

Slightly soluble in water.

BRN 

261917

InChI

InChI=1S/C12H20N4O2/c17-11(15-7-3-1-4-8-15)13-14-12(18)16-9-5-2-6-10-16/h1-10H2

InChIKey

OQJBFFCUFALWQL-UHFFFAOYSA-N

SMILES

N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O

CAS DataBase Reference

10465-81-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3234

WGK Germany 

3

TSCA 

No

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1,1'-(Azodicarbonyl)-dipiperidine Usage And Synthesis

Description

1,1''-(Azodicarbonyl)dipiperidine (ADDP) is a reagent commonly used in the Mitsunobu reaction for the condensation of an alcohol and an acidic compound. It has been used as a reagent in the synthesis of G protein-coupled receptor 120 (GPR120) agonists with antidiabetic activity and peroxisome proliferator-activated receptor α (PPARα), PPARγ, and PPARδ triple agonists.

Chemical Properties

yellow crystalline powder

Uses

It is used in a study of the copper-catalyzed addition of aryboronic acids to azodicarboxyl derivatives providing aryl-substituted hydrazides. It is widely used reagent for the Mitsunobu reaction. It is reactant for preparation of polyfluoroalkylated tripyrazolylmethane ligands, (-)-Hygromycin A via Mitsunobu glycosylation, optically active α,α-disubstituted amino acids via Mitsunobu reaction, aza-β-lactams through [2+2] cycloaddition reactions, glycosyl disulfides, pyridine ether PPAR agonists, S-glycosyl amino acid, building blocks for combinatorial neoglycopeptide synthesis and is a histamine H3 receptor antagonists. It is a reactant for Mitsunobu inversion reactions.

Reactions

1,1'-(Azodicarbonyl)-dipiperidine can selectively oxidizes a variety of alcohols to the corresponding aldehydes or ketones under basic conditions.

IC 50

PPARα; PPAR-γ; PPARδ

References

[1] TETSUTO TSUNODA ?  Sh? I  Yoshiko Yamamiya. 1,1′-(azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction[J]. Tetrahedron Letters, 1993, 34 10: Pages 1639-1642. DOI: 10.1016/0040-4039(93)85029-v
[2] DAISUKE HIROSE. Systematic Evaluation of 2-Arylazocarboxylates and 2-Arylazocarboxamides as Mitsunobu Reagents[J]. The Journal of Organic Chemistry, 2018, 83 8: 4712-4729. DOI: 10.1021/acs.joc.8b00486
[3] XUQING ZHANG . Design, synthesis and SAR of a novel series of heterocyclic phenylpropanoic acids as GPR120 agonists[J]. Bioorganic & Medicinal Chemistry Letters, 2017, 27 15: Pages 3272-3278. DOI: 10.1016/j.bmcl.2017.06.028
[4] JOHN P MOGENSEN. Design and synthesis of novel PPARα/γ/δ triple activators using a known PPARα/γ dual activator as structural template[J]. Bioorganic & Medicinal Chemistry Letters, 2003, 13 2: Pages 257-260. DOI: 10.1016/s0960-894x(02)00881-8

1,1'-(Azodicarbonyl)-dipiperidine(10465-81-3)Related Product Information

• N,N,N',N'-Tetramethylazodicarboxamide
• O-Phthalimide
• Diethyl azodicarboxylate
• Dimethyl phthalate
• DIPHENYLCARBAZONE
• Azodicarbonamide
• 2,2'-Azobis(2-methylpropionitrile)
• AZODICARBOXYLIC BISMORPHOLIDE
• Dibenzyl azodicarboxylate
• Diisopropyl azodicarboxylate
• Di-tert-Butyl azodicarboxylate
• Bis(4-chlorobenzyl) azodicarboxylate
• N-Formylpiperidine
• 1,1-DIETHYLUREA
• 1-CARBAMYLPIPERIDINE
• 1,1'-(Azodicarbonyl)-dipiperidine