N-Nitrosopiperidine

Base Information

• Chemical Name: N-Nitrosopiperidine
• CAS No.: 100-75-4
• Deprecated CAS: 68374-62-9
• Molecular Formula: C5H10 N2 O
• Molecular Weight: 114.147
• Hs Code.: 2933399090
• European Community (EC) Number: 202-886-6
• NSC Number: 138
• UN Number: 2811,3082
• UNII: 6N066XUL4L
• DSSTox Substance ID: DTXSID8021060
• Nikkaji Number: J4.014B
• Wikidata: Q22138417
• NCI Thesaurus Code: C44423
• ChEMBL ID: CHEMBL165244
• Mol file: 100-75-4.mol

Synonyms:N-nitrosopentamethyleneimine;N-nitrosopiperidine;nitrosopiperidine

Chemical Property of N-Nitrosopiperidine

Chemical Property:

• Appearance/Colour: light yellow oily liquid
• Vapor Pressure: 0.103mmHg at 25°C
• Melting Point: 170℃ (decomposition)
• Refractive Index: 1.4933 (589.3 nm 19℃)
• Boiling Point: 229.8 ºC
• PKA: -3.18±0.20(Predicted)
• Flash Point: 92.8 ºC
• PSA: 32.67000
• Density: 1.06 g/mL(lit.)
• LogP: 1.09160
• Storage Temp.: 2-8°C
• Water Solubility.: 1-5 g/100 mL at 22 C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 114.079312947
• Heavy Atom Count: 8
• Complexity: 78.5
• Transport DOT Label: Poison

Purity/Quality:

Neuronal Pentraxin I ^*data from reagent suppliers

Safty Information:

• Pictogram(s): TF
• Hazard Codes: T,F
• Statements: 25-40-39/23/24/25-23/24/25-11
• Safety Statements: 53-23-26-36/37/39-45-36/37-16-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrosamines
• Canonical SMILES: C1CCN(CC1)N=O
• Uses: A carcinogenic nitrosocompound.

Technology Process of N-Nitrosopiperidine

There total 36 articles about N-Nitrosopiperidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

piperidine (110-89-4) → N-nitrosopiperidine (100-75-4)

Guidance literature:

With [NO⁽¹⁺⁾*18-crown-6*H(NO₃)2^(1-)]; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1021/jo001729t

Reference yield: 86.0%

piperidine (110-89-4) + 3,4-dinitro-1-methyl-1H-pyrrole (68712-54-9) → N-nitrosopiperidine (100-75-4) + 2,3-dinitro-1,4-dipiperidino-buta-1,3-diene (19985-38-7) + 1-methyl-4-nitro-2-piperidinopyrrole (74460-26-7)

Guidance literature:

In acetonitrile; for 30h; Product distribution; Heating; 2 equiv of piperidine, or morpholine instead of piperidine; var. times;

DOI:10.1021/jo00150a005

Reference yield: 82.0%

1-ethyl-piperidine (766-09-6) → N-nitrosopiperidine (100-75-4)

Guidance literature:

With dinitrogen tetroxide impregnated on activated charcoal; In tetrachloromethane; for 12h; Heating;

DOI:10.1081/SCC-200057999

upstream raw materials:

piperidine

piperidinium nitrate

acetic anhydride

piperidine; nitrite

Downstream raw materials:

1-Aminopiperidine

piperidine

di(N-piperidinyl)methane

9,9'-bianthracene

Refernces

• 1、 Gaur, Pinki,Banerjee, Shaibal. "Oxone-sodium nitrite mediated N-nitrosamines formation under mild conditions from secondary amines". . p. 2270 - 2279. Retrieved 2019.
• 2、 Demir,Mahasneh,Aksoy,Gercek. "The mild N-nitrosation of secondary amines with trichloro nitromethane". . p. 2607 - 2611. Retrieved 1992.
• 3、 Zolfigol, Mohammad Ali,Shirini, Farhad,Ghorbani Choghamarani, Arash. "Silica chloride/NaNO2 as a novel heterogeneous system for the nitrosation of secondary amines under mild conditions". . p. 1809 - 1813. Retrieved 2002.
• 4、 Zolfigol, Mohammad Ali,Habibi, Davood,Mirjalili, BiBi Fatemeh,Bamoniri, Abdolhamid. "The use of Nafion-H/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions". . p. 3345 - 3349. Retrieved 2003.
• 5、 Makhova et al.. "-". . . Retrieved 1978.
• 6、 Garcia-Rio,Leis,Iglesias. "Nitrosation of Amines in Nonaqueous Solvents. 2. Solvent-Induced Mechanistic Changes". . p. 4712 - 4720. Retrieved 1997.
• 7、 Niknam, Khodabakhsh,Zolfigol, Mohammad Ali. "Alumina-methanesulfonic acid (AMA)/NaNO2 as an efficient procedure for the chemoselectivite N-nitrosation of secondary amines". . p. 2311 - 2319. Retrieved 2006.
• 8、 Garcia-Santos,Calle,Gonzalez-Mancebo,Casado. "Kinetics of the Aminolysis and Hydrolysis of Alkyl Nitrites: Evidence for an Orbital Controlled Mechanism". . p. 997 - 1003. Retrieved 1996.
• 9、 Zolfigol, Mohammad Ali,Bamoniri, Abdolhamid. "Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the chemoselective N-nitrosation of secondary amines under mild conditions". . p. 1621 - 1624. Retrieved 2002.
• 10、 Garcia-Rio, Luis,Leis, Jose R.,Moreira, Jose A.,Serantes, David. "Nitrosation of Amines in Non-Aqueous Solvents - Difference between N-N=O and O-N=O Nitroso Donors". . p. 614 - 622. Retrieved 2004.