N-[(piperidine-1-carbonyl)imino]piperidine-1-carboxamide

• ChemBase ID: 151260
• Molecular Formular: C12H20N4O2
• Molecular Mass: 252.3128
• Monoisotopic Mass: 252.1586259
• SMILES: C1CCN(CC1)C(=O)/N=N/C(=O)N1CCCCC1
• Canonical SMILES: O=C(N1CCCCC1)/N=N/C(=O)N1CCCCC1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(piperidine-1-carbonyl)imino]piperidine-1-carboxamide; (NE)-N-{[(E)-piperidine-1-carbonyl]imino}piperidine-1-carboxamide
• IUPAC Traditional name: N-(piperidine-1-carbonylimino)piperidine-1-carboxamide; (NE)-N-[(E)-piperidine-1-carbonylimino]piperidine-1-carboxamide
• Synonyms: 1,1′-Azobis(N,N-pentamethyleneformamide); ADD; NSC 356027; SR 4077; Azodicarboxylic acid dipiperidide; 1,1′-(Azodicarbonyl)dipiperidine; 1,1-(azodicarbonyl)dipiperidine; 1,1'-(Azodicarbonyl)dipiperidine; 1,1'-(Azodicarbonyl)dipiperidine; ADDP; Azodicarboxylic dipiperidide; Azodicarboxylic acid dipiperidide; 偶氮二甲酰二哌啶; 1,1'-(偶氮二羰基)二哌啶; 1,1'-(偶氮二羰基)二哌啶; 偶氮二甲酰二哌啶

Database IDs

• CAS Number: 10465-81-3
• MDL Number: MFCD00010111
• Beilstein Number: 261917
• PubChem SID: 24847283; 24855495; 162245416
• PubChem CID: 5702657

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.74944675
• LogD (pH = 7.4): 0.74944675
• Log P: 0.74944675
• Molar Refractivity: 66.956 cm^3
• Polarizability: 25.547024 Å^3
• Polar Surface Area: 65.34 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 132-136 °C(lit.); 133-136°C; 134-136 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.5% (TLC); 97%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C12H20N4O2

DETAILS

Sigma Aldrich - 255920

Application
Used in a study of the copper-catalyzed addition of aryboronic acids to azodicarboxyl derivatives providing aryl-substituted hydrazides.10
Widely used reagent for the Mitsunobu reaction
Reactant for preparation of:
• Polyfluoroalkylated tripyrazolylmethane ligands1
• (-)-Hygromycin A via Mitsunobu glycosylation2
• Optically active α,α-disubstituted amino acids via Mitsunobu reaction3
• Aza-β-lactams through [2+2] cycloaddition reactions4
• Glycosyl disulfides5
• Pyridine ether PPAR agonists6
• S-glycosyl amino acid building blocks for combinatorial neoglycopeptide synthesis7
• Histamine H3 receptor antagonists8Reactant for:
• Mitsunobu inversion reactions9
Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 11632

Other Notes
Reagent introduced for the Mitsunobu reaction of acids with high pK′s; excess reagent and reaction products can be readily removed by filtration (after dilution with hexane) 1,2

REFERENCES

• Reagent for the Mitsunobu reaction (see Diethyl azodicarboxylate, L19348), used in combination with tri-n-butylphosphine as a more powerful system than DEAD for higher pK_a nucleophiles: Tetrahedon Lett., 34, 1639 (1993); Tetrahedron, 61, 6218 (2005). Has also been utilized in a selective method for converting primary and secondary alcohols to carbonyl compounds, by reaction of the alcohol with a Grignard reagent, followed by oxidation of the intermediate magnesio-derivative with ADDP: J. Org. Chem., 38, 1652 (1973); Bull. Chem. Soc. Jpn., 2773 (1977).