| Identification | More | [Name]
1,1'-(Azodicarbonyl)-dipiperidine | [CAS]
10465-81-3 | [Synonyms]
1,1'-(AZODICARBONYL)DIPIPERIDINE
AZODICARBOXYLIC ACID DIPIPERIDIDE
Azodicarboxylic acid dipiperidine
AZODICARBOXYLIC DIPIPERIDIDE
sr4077
Diphenylpiperidylcarboxylate
AZODICARBOXYLIC ACID DIPIPERIDYL ESTER
Azodicarboxylic
diazenedicarboxylic acid bis(N,N-piperidide)
1,1-IAZODICARBONYL)DIPIPERIDINE
1,1'-(azodicarbonyl)piperidine
ADD, Azodicarboxylic acid dipiperidide
ADD, ADDP, Azodicarboxylic dipiperidide
ADDP (1,1-Aza dicarbonyl di piperidine)
1,1'-(Azobiscarbonyl)dipiperidine
1,1'-(Azodicarbonyl)bispiperidine
Bis(piperidinocarbonyl)diazene
Bis(piperidinocarbonyl)diimide | [Molecular Formula]
C12H20N4O2 | [MDL Number]
MFCD00010111 | [Molecular Weight]
252.31 | [MOL File]
10465-81-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline powder | [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) | [form ]
solid | [pka]
-0?+-.0.20(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
3234 | [WGK Germany ]
3 | [TSCA ]
No | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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.1,2 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.3,4 | [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 | [Solubility in organics]
1,1'-(Azodicarbonyl)-dipiperidine is insol petroleum ether; slightly sol methanol; sol ethanol, ether, THF. | [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 |
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