(S)-6-Chloronicotine

Base Information

• Chemical Name: (S)-6-Chloronicotine
• CAS No.: 112091-17-5
• Molecular Formula: C10H13ClN2
• Molecular Weight: 196.68
• UNII: YT5WAL3YF3
• DSSTox Substance ID: DTXSID90442718
• Nikkaji Number: J873.891B
• Wikipedia: 6-Chloronicotine
• Wikidata: Q82260160
• Mol file: 112091-17-5.mol

Synonyms:(S)-6-Chloronicotine;112091-17-5;6-Chloronicotine;(S)-2-chloro-5-(1-methylpyrrolidin-2-yl)pyridine;2-chloro-5-[(2S)-1-methylpyrrolidin-2-yl]pyridine;6-Chloro-nicotine;Nicotine, 6-chloro-;YT5WAL3YF3;SCHEMBL611690;Pyridine, 2-chloro-5-[(2S)-1-methyl-2-pyrrolidinyl]-;DTXSID90442718;SVVOLGNZRGLPIU-VIFPVBQESA-N;F13104;EN300-6478527;2-Chloro-5-((S)-1-methyl-pyrrolidin-2-yl)-pyridine;2-Chloro-5-[(2S)-1-methyl-2-pyrrolidinyl]pyridine

Chemical Property of (S)-6-Chloronicotine

Chemical Property:

• Boiling Point: 277.0±40.0 °C(Predicted)
• PKA: 7.63±0.70(Predicted)
• PSA: 16.13000
• Density: 1.162±0.06 g/cm3(Predicted)
• LogP: 2.43960
• Storage Temp.: -20°C Freezer
• Solubility.: DCM, Ethyl Acetate, Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 196.0767261
• Heavy Atom Count: 13
• Complexity: 174

Purity/Quality:

(S)-6-Chloronicotine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCCC1C2=CN=C(C=C2)Cl
• Isomeric SMILES: CN1CCC[C@H]1C2=CN=C(C=C2)Cl
• Uses: (S)-(-)-Nicotine (N412450) derivative.

Technology Process of (S)-6-Chloronicotine

There total 18 articles about (S)-6-Chloronicotine 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: 88.6%

(S)-6-hydroxy-D-nicotine (10516-09-3) → (S)-6-chloronicotine (112091-17-5)

Guidance literature:

With phosphorus pentachloride; In trichlorophosphate; at 40 - 92 ℃; for 1h;

DOI:10.3987/com-97-7827

Reference yield: 87.0%

nicotin (54-11-5) → (S)-6-chloronicotine (112091-17-5)

Guidance literature:

nicotin; With n-butyllithium; In 2-(N,N-dimethylamino)ethanol; hexane; at -20 ℃; for 2.5h; Inert atmosphere;

With hexachloroethane; at -78 - 1 ℃; Inert atmosphere;

DOI:10.1021/ol101887b

Reference yield: 87.0%

nicotin (54-11-5) → (S)-2-chloro-3-(1-methylpyrrolidin-2-yl)pyridine + (S)-6-chloronicotine (112091-17-5)

Guidance literature:

nicotin; With n-butyllithium; 2-(N,N-dimethylamino)ethanol; In hexane; at -20 ℃; for 1h;

With hexachloroethane; In hexane; at -78 ℃; for 1h;

DOI:10.1021/ol052196j

upstream raw materials:

methylamine

4-(6-chloropyridin-3-yl)-4-oxobutyraldehyde

6-Chloronicotinoyl chloride

6-chloro-N-methoxy-N-methylpyridine-3-carboxamide

Downstream raw materials:

(S)-6-chloro-5-iodonicotine

[5-((2S)-1-methylpyrrolidin-2-yl)-2-chloro(4-pyridyl)]diphenylmethan-1-ol

(1R)-[5-((2S)-1-methylpyrrolidin-2-yl)-2-chloro(4-pyridyl)](2,3,4,5,6-pentaflurophenyl)methan-1-ol

(1S)-[5-((2S)-1-methylpyrrolidin-2-yl)-2-chloro(4-pyridyl)](2,3,4,5,6-pentaflurophenyl)methan-1-ol