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| | 1,1'-(Azodicarbonyl)-dipiperidine Basic information |
| | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | 3234 | | WGK Germany | 3 | | TSCA | No | | HS Code | 29339900 |
| | 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 Preparation Products And Raw materials |
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