36508-80-2

Basic information

• Product Name: 1-methyl-5-(1-oxidopyridin-5-yl)-pyrrolidin-2-one
• Synonyms: 1-methyl-5-(1-oxidopyridin-5-yl)-pyrrolidin-2-one;(5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone;1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-Oxide;(5S)-1-Methyl-5-[(pyridine 1-oxide)-3-yl]pyrrolidin-2-one;3-[(5S)-1-Methyl-2-oxopyrrolidin-5-yl]pyridine 1-oxide;2-Pyrrolidinone, 1-methyl-5-(1-oxido-3-pyridinyl)-, (5S)-;2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, N-oxide, (S)-;Ccris 7626
• CAS NO: 36508-80-2
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.22
• Product Categories: Metabolites & Impurities;Nicotine Derivatives;Heterocycles
• Mol File: 36508-80-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 116-117°C
• Boiling Point: 475.4°Cat760mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: -20°C Freezer
• Stability: Moisture Sensitive - Seal Tightly and Store in Freezer
• CAS DataBase Reference: 1-methyl-5-(1-oxidopyridin-5-yl)-pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-5-(1-oxidopyridin-5-yl)-pyrrolidin-2-one(36508-80-2)
• EPA Substance Registry System: 1-methyl-5-(1-oxidopyridin-5-yl)-pyrrolidin-2-one(36508-80-2)

Safety Data

• Hazardous Substances Data: 36508-80-2(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Uses

A major metabolite of Nicotine (N412450) in humans. Carcinogen.

Definition

ChEBI: An N-alkylpyrrolidine that is nicotine in which the methylene hydrogens at position 2 on the pyrrolidine ring have been replaced by an oxo group and the pyridine nitrogen converted to the corresponding N-oxide. A minor metabolite of nicotine.

InChI:InChI=1/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 2820-55-5 nicotine nitrogen oxide 
• 67-56-1 methanol 

Relevant articles and documents

Enamine trapping with the oxidation of nicotine and analogues

Various N-tertiary pyrrolidine derivatives 1 and 6-9 bearing voluminous substituents in 2-position react with Hg(II)-EDTA under double dehydrogenation and an atypical direction to the secondary C-5 with formation of the corresponding lactams 2 and 12-15. The primary products of a two electron withdrawal cannot be isolated. By addition of substituted benzaldehydes b-d as trapping reagents to the Hg(II)-EDTA solution additionally are received condensation products of the type of benzylidene lactams 1b-d, 6b,c and 7b-9b. Here the total yield of isolated products increases, while simultaneously the yield of unsubstituted lactams of the type 2 and 12-15 decreases. Therefore the atypical direction of dehydrogenation with the trapping aldehydes is the same as with the lactam forming pyrrolidines. Additionally the detection of the enamine species in the first stage of dehydrogenation with following reaction to the condensation product is secured. The (E)-configuration of 1b is confirmed by the chemical shift of the proton a-H and the 19F/13C-coupling constant of C-4 by direct comparison with its (Z)-isomer 27. The similar signal dates of the enone protons in the other prepared benzylidene lactams 1c,d, as well as 6b,c and 7b-9b verify also the (E)-configuration.