1,1'-(Azodicarbonyl)dipiperidine

HCID 73042CAS 10465-81-3

Substructure search Find similar structures

Basic information

Standard SMILES: O=C(N=NC(=O)N1CCCCC1)N1CCCCC1
InChIKey: OQJBFFCUFALWQL-UHFFFAOYSA-N
Molecular formula: C12H20N4O2
Average molar mass: 252.31 g/mol
Monoisotopic mass: 252.15862589

Names & identifiers

Preferred name: 1,1'-(Azodicarbonyl)dipiperidine
IUPAC: N-(piperidine-1-carbonylimino)piperidine-1-carboxamide
English name: 1,1'-(Azodicarbonyl)-dipiperidine
Molecular formula: C12H20N4O2
Molecular weight: 252.31

Names & synonyms

1,1'-(Azodicarbonyl)dipiperidinediazene-1,2-diylbis(piperidin-1-ylmethanone)1,1'-(Azodicarbonyl)-dipiperidineAzodicarboxylic acid dipiperidide1,1-(Azodicarbonyl)-DipiperidineN-(piperidine-1-carbonylimino)piperidine-1-carboxamide871024-86-1(E)-diazene-1,2-diylbis(piperidin-1-ylmethanone)AdDPMFCD00010111Piperidine, 1,1'-(azodicarbonyl)bis-(E)-1,1 inverted exclamation mark -(Azodicarbonyl)dipiperidine

Show more names

(NE)-N-(piperidine-1-carbonylimino)piperidine-1-carboxamidesr4077NSC 356027Azodicarboxylic1,1'-(Azodicarbo1,1'-(Azodicarbonyl)Diphenylpiperidylcarboxylate

azodicarbonyldipiperidine1,1'-[azodicarbonyl]dipiperidine1,1'-Azobis(N,N-pentamethyleneformamide)Azodicarbonyl dipiperidine(azodicarbonyl)dipiperidineN-[(piperidine-1-carbonyl)imino]piperidine-1-carboxamideSCHEMBL10791Methanone, 1,1'-(1E)-1,2-diazenediylbis[1-(1-piperidinyl)-

Database identifiers

CAS: 10465-81-3
PubChem CID: 73042
DTXSID: DTXSID001377440

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 65.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 18
Formal charge: 0
Complexity: 299

Physicochemical properties

Melting point: 132 · 132-136 °C(lit.)
Boiling point: 366.4 · 366.4±25.0 °C(Predicted)
Density: 1.29 · 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+-.0.20(Predicted)
form: solid
color: yellow
Water Solubility: Slightly soluble in water.
BRN: 261917 · 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 · 10465-81-3(CAS DataBase Reference)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
RIDADR: 3234 · 3234
WGK Germany: 3 · 3
TSCA: No
HS Code: 29339900 · 29339900

Safety & regulation

Safety data

wgk: 3
tsca: No
ridadr: 3234
hs_code: 29339900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Hazard statements: H315-H319-H335
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Description1,1''-(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.

UsesIt 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.