3-(1-Nitrosopyrrolidin-2-yl)pyridine

Base Information

• Chemical Name: 3-(1-Nitrosopyrrolidin-2-yl)pyridine
• CAS No.: 80508-23-2
• Deprecated CAS: 84237-38-7
• Molecular Formula: C9H11N3O
• Molecular Weight: 177.206
• Hs Code.: 29333990
• European Community (EC) Number: 635-203-9,635-909-7
• DSSTox Substance ID: DTXSID60860182
• Nikkaji Number: J2.745F
• Wikipedia: N-Nitrosonornicotine
• Metabolomics Workbench ID: 49645
• ChEMBL ID: CHEMBL434108
• Mol file: 80508-23-2.mol

Synonyms:N'-nitrosonornicotine;N'-nitrosonornicotine, (+-)-isomer;N'-nitrosonornicotine, (S)-isomer;N-nitrosonor-nicotine;N-nitrosonornicotine;nitrosonornicotine

Chemical Property of 3-(1-Nitrosopyrrolidin-2-yl)pyridine

Chemical Property:

• Melting Point: 43-45oC
• Boiling Point: 369.5±35.0 °C(Predicted)
• PKA: 5.16±0.12(Predicted)
• Flash Point: 9℃
• PSA: 45.56000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 1.83780
• Storage Temp.: -20°C Freezer
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 177.090211983
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

NLT 98% ^*data from raw suppliers

rac-N’-NitrosoNornicotine(1.0mg/mLinAcetonitrile) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 25-40-39/23/24/25-23/24/25-11
• Safety Statements: 36/37-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(N(C1)N=O)C2=CN=CC=C2
• Uses: rac N'-Nitrosonornicotine is a tobacco alkaloid known as esophageal carcinogen. rac N'-Nitrosonornicotine is the cause of esophageal and oral cavity cancer in smokers and snuff dippers. The studies showed that the carcinogenicity of (S)-NNN, the predominant enantiomer in tobacco products, may be greater than that of (R)-NNN or racemic NNN.

Technology Process of 3-(1-Nitrosopyrrolidin-2-yl)pyridine

There total 4 articles about 3-(1-Nitrosopyrrolidin-2-yl)pyridine 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: 5.0%

3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5) → cotinine (15569-85-4) + 3-(1-nitroso-pyrrolidin-2-yl)-pyridine (80508-23-2,350508-22-4,350508-30-4,61601-78-3,84237-38-7) + N'-nitrosonorcotinine (74804-85-6)

Guidance literature:

With silver(I) nitrite; In N,N-dimethyl-formamide; at 70 ℃;

Reference yield:

Myosmine (532-12-7) → 4-(3-pyridyl)-4-oxobutanol (59578-62-0) + 3-(1-nitroso-pyrrolidin-2-yl)-pyridine (80508-23-2,350508-22-4,350508-30-4,61601-78-3,84237-38-7)

Guidance literature:

With human gastric juice; sodium nitrite; at 37 ℃; for 0.5h; Further Variations:; Reagents; Product distribution;

DOI:10.1021/jf9903004

Reference yield:

ethyl N-methyl-N-<4-chloro-4-(3-pyridyl)butnyl>carbamate (73130-52-6) → 3-(1-nitroso-pyrrolidin-2-yl)-pyridine (80508-23-2,350508-22-4,350508-30-4,61601-78-3,84237-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 10percent aq. sulphuric acid / 5 h / Heating; further reagent

2: 71 percent / silver nitrite / dimethylformamide / 70 °C

With silver(I) nitrite; sulfuric acid; In N,N-dimethyl-formamide;

upstream raw materials:

3-(1-methyl-pyrrolidin-2-yl)-pyridine

Myosmine

ethyl N-methyl-N-<4-chloro-4-(3-pyridyl)butnyl>carbamate

Downstream raw materials:

N'-Nitrosonornicotine 1-N-oxide

pyridyl-N-β-D-glucopyranuronosyl-N'-nitrosonornicotinium inner salt

Refernces

• 1、 Acheson, R. Morrin,Ferris, Michael J.,Sinclair, Neil M.. "Transformations involving the Pyrrolidine Ring of Nicotine". . p. 579 - 585. Retrieved 2007/10/02.