N-Nitrosopyrrolidine

Base Information

• Chemical Name: N-Nitrosopyrrolidine
• CAS No.: 930-55-2
• Deprecated CAS: 68374-63-0
• Molecular Formula: C4H8 N2 O
• Molecular Weight: 100.12
• Hs Code.: 2933990090
• European Community (EC) Number: 213-218-8,881-737-2
• NSC Number: 18797
• UN Number: 2810,3082
• UNII: SZ4J5WK201
• DSSTox Substance ID: DTXSID8021062
• Nikkaji Number: J3.349I
• Wikidata: Q22138421
• NCI Thesaurus Code: C44424
• Metabolomics Workbench ID: 45012
• ChEMBL ID: CHEMBL351175
• Mol file: 930-55-2.mol

Synonyms:N Nitrosopyrrolidine;N-Nitrosopyrrolidine

Chemical Property of N-Nitrosopyrrolidine

Chemical Property:

• Appearance/Colour: Light-Yellow Oil
• Vapor Pressure: 0.233mmHg at 25°C
• Refractive Index: n20/D 1.489(lit.)
• Boiling Point: 214°Cat760mmHg
• PKA: -3.14±0.20(Predicted)
• Flash Point: 83.3°C
• PSA: 32.67000
• Density: 1.24g/cm³
• LogP: 0.70150
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Ethyl Acetate, Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 100.063662883
• Heavy Atom Count: 7
• Complexity: 68.1
• Transport DOT Label: Poison

Purity/Quality:

98%,99%, ^*data from raw suppliers

NPY1R ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 40

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrosamines
• Canonical SMILES: C1CCN(C1)N=O
• Description: N-Nitrosopyrrolidine (NPYR) is a nitrosamine compound that is used primarily as a research chemical and is not produced commercially. There is the possibility of generating NPYR after frying in dry-cured bacon. The major amine precursors to NPYR in cooked bacon are free proline in the adipose tissue and to a lesser extent, collagenous connective tissues. When proline peptides were heated with nitrite at pH 3.4, small amounts of NPYR were formed from all tested peptides. There are several potential sources of exposure of man to this group of potent carcinogens. Certain foods were thought to be derived from the interaction of nitrite with secondary amines in the food, either spontaneously or by the agency of bacteria. Recently the possibility that nitrosamines may be formed from secondary amines and nitrite in the gastrointestinal tract has been explored. The acid conditions that prevail in the human stomach favor the nitrosation of dimethylamine. In addition, at neutral pH, many secondary amines can be nitrosated by nitrite or nitrate in the presence of intestinal bacteria, or the cecal contents of the rat, and soluble enzymes which catalyze the N-nitrosation of several secondary amines have been extracted from two microorganisms. The rate of nitrosamine formation depends greatly on the basicity of the amine; the less basic amines such as diphenylamine and pyrrolidine are nitrosated far more readily than the strongly basic dimethylamine and diethylamine.
• Uses: One of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis, but the toxicological mechanisms involved have not been elucidated. 1-Nitrosopyrrolidine is one of the N-nitroso compounds (NOCs) implicated in human colon carcinogenesis (1,2,3) but the toxicological mechanisms involved have not been elucidated. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

Technology Process of N-Nitrosopyrrolidine

There total 21 articles about N-Nitrosopyrrolidine 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: 98.0%

pyrrolidine (123-75-1) → N-nitrosopyrrolidine (930-55-2)

Guidance literature:

With sulfuric acid; silica gel; sodium nitrite; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2002-34230

Reference yield: 70.0%

C6H12NO(1+)*CH3O4S(1-) (73722-93-7) → pyrrolidine (123-75-1) + 1-pyrrolidinecarboxaldehyde (3760-54-1) + N-nitrosopyrrolidine (930-55-2)

Guidance literature:

With sodium nitrite; In water;

Reference yield: 62.0%

pyrrolidine (123-75-1) + bromonitromethane (563-70-2) → N-nitrosopyrrolidine (930-55-2) + formaldehyd (50-00-0,30525-89-4,61233-19-0)

Guidance literature:

In acetonitrile; at 70 ℃; for 168h;

DOI:10.1039/c39900001598

upstream raw materials:

pyrrolidine

n-propyl nitrite

n-Butyl nitrite

bromonitromethane

Downstream raw materials:

[(5,10,15,20-tetraphenylporphyrinato)Fe(N-nitrosopyrrolidine)2]ClO₄

2-hydroxytetrahydrofuran

pyrrolidine

N-aminopyrrolidine

Refernces

• 1、 Chen, Zuxing,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wang, Feiyi,Wang, Ying,Yang, Guichun,You, Shiqi. "The Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N-Nitrosation of Secondary Amines". supporting information. p. 3289 - 3293. Retrieved 2021/07/02.
• 2、 Zhao, Ji-Ping,Ding, Lu-jia,Wang, Peng-Cheng,Liu, Ying,Huang, Min-Jun,Zhou, Xin-Li,Lu, Ming. "Electrochemical Nonacidic N-Nitrosation/N-Nitration of Secondary Amines through a Biradical Coupling Reaction". supporting information. p. 5036 - 5043. Retrieved 2020/07/13.