A Mitsunobu reagent
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1,1'-(Azodicarbonyl)dipiperidine

Item No. 30486

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,1′-(1,2-diazenediyl)bis[1-(1-piperidinyl)-methanone
CAS Number
10465-81-3
Synonyms
  • ADDP
  • NSC 356027
Molecular Formula
C12H20N4O2
Formula Weight
252.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlEthanol: 1 mg/ml
SMILES
O=C(/N=N/C(N1CCCCC1)=O)N2CCCCC2
InChi Code
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/b14-13+
InChi Key
OQJBFFCUFALWQL-BUHFOSPRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

    $86

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    10 g

    $153

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    Cayman Chemical
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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tsunoda, T., Yamamiya, Y., and Itô, S. 1,1′-(Azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for Mitsunobu reaction. Tetrahedron Lett. 34(10), 1639-1642 (1993).

    2. Hirose, D., Gazvoda, M., Košmrlj, J., et al. Systematic evaluation of 2-arylazocarboxylates and 2-arylazocarboxamides as Mitsunobu reagents. The Journal of Organic Chemistry 83(8), 4712-4729 (2018).

    3. Zhang, X., Cai, C., Winters, M., et al. Design, synthesis and SAR of a novel series of heterocyclic phenylpropanoic acids as GPR120 agonists. Bioorg. Med. Chem. Lett. 27(15), 3272-3278 (2017).

    4. Mogensen, J.P., Jeppesen, L., Bury, P.S., et al. Design and synthesis of novel PPARα/γ/δ triple activators using a known PPARα/γ dual activator as structural template. Bioorg. Med. Chem. Lett. 13(2), 257-260 (2003).