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10465-81-3 molecular structure
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N-[(piperidine-1-carbonyl)imino]piperidine-1-carboxamide

ChemBase ID: 151260
Molecular Formular: C12H20N4O2
Molecular Mass: 252.3128
Monoisotopic Mass: 252.1586259
SMILES and InChIs

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

Cite this record

CBID:151260 http://www.chembase.cn/molecule-151260.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
10465-81-3
MDL Number
MFCD00010111
Beilstein Number
261917
PubChem SID
162245416
24855495
24847283
PubChem CID
5702657

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 0.74944675  LogD (pH = 7.4) 0.74944675 
Log P 0.74944675  Molar Refractivity 66.956 cm3
Polarizability 25.547024 Å3 Polar Surface Area 65.34 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
132-136 °C(lit.) expand Show data source
133-136°C expand Show data source
134-136 °C(lit.) expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥98.5% (TLC) expand Show data source
97% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Empirical Formula (Hill Notation)
C12H20N4O2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 255920 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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 pKa 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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