rac Cotinine

Base Information

• Chemical Name: rac Cotinine
• CAS No.: 15569-85-4
• Molecular Formula: C10H12 N2 O
• Molecular Weight: 176.218
• Mol file: 15569-85-4.mol

Synonyms:2-Pyrrolidinone,1-methyl-5-(3-pyridinyl)-, (?à)-; Cotinine, (?à)- (8CI); (?à)-Cotinine;1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone

Chemical Property of rac Cotinine

Chemical Property:

• Vapor Pressure: 0.000421mmHg at 25°C
• Melting Point: 48-50°C
• Refractive Index: 1.555
• Boiling Point: 316°C at 760 mmHg
• PKA: 4.72±0.12(Predicted)
• Flash Point: 166.7°C
• PSA: 33.20000
• Density: 1.146g/cm³
• LogP: 1.31280
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly) , Dichloromethane (Slightly), Ethanol (Slightly), Methanol

Purity/Quality:

97% ^*data from raw suppliers

rac cotinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A major metabolite of Nicotine in humans. Carcinogen.

Technology Process of rac Cotinine

There total 23 articles about rac Cotinine 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: 97.0%

N-methyl-2,2-bis(phenylsulfanyl)-N-<1-(3-pyridyl)vinyl>acetamide (142609-31-2) → cotinine (15569-85-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

Reference yield: 90.0%

3-Bromopyridine (626-55-1,163928-56-1) + 1-methyl-pyrrolidin-2-one (872-50-4,26138-58-9) → cotinine (15569-85-4)

Guidance literature:

With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium carbonate; In benzene; at 20 ℃; for 72h; regioselective reaction; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.8b07405

Reference yield: 88.0%

3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5) → cotinine (15569-85-4)

Guidance literature:

With Hg(II)-EDTA; In dichloromethane; for 17h; Heating; pH 8.0;

upstream raw materials:

nicotin

N-methyl-2,2-bis(phenylsulfanyl)-N-<1-(3-pyridyl)vinyl>acetamide

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

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

Downstream raw materials:

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

cotinine

(S)-(-)-1-methyl-5-(3-pyridyl)-2-pyrrolidinone

dimethyl 3-benzoyl-6-(1-methyl-5-oxopyrrolidin-2-yl)indolizine-1,2-dicarboxylate

Refernces

• 1、 Vincek,Martin,Aceto,Tripathi,May,Harris. "Synthesis of 4,4-ditritio-(+)-nicotine: Comparative binding and distribution studies with natural enantiomer". . p. 1292 - 1293. Retrieved 1981.
• 2、 -. "Preparation method of artificially synthesized nicotine". Paragraph 0025; 0030-0031; 0034-0035; 0040-0041; 0045; 0050. . Retrieved 2019/10/04.
• 3、 -. "Oil composition". . . Retrieved 2007/10/04.