Nornicotine-2-carboxylic Acid

Base Information

• Chemical Name: Nornicotine-2-carboxylic Acid
• CAS No.: 3562-11-6
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.217
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70602358
• Nikkaji Number: J391.270A
• Mol file: 3562-11-6.mol

Synonyms:Nornicotine-2-carboxylic Acid;3562-11-6;5-(pyridin-3-yl)pyrrolidine-2-carboxylic acid;5-pyridin-3-ylpyrrolidine-2-carboxylic acid;5-Pyridin-3-ylproline;Nornicotine-2-carboxylicAcid;SCHEMBL2460326;DTXSID70602358;AKOS022700246;AS-59657;CS-0269348;EN300-305011;Proline, 5-(3-pyridinyl)-;Proline, 5-(3-pyridyl)- (7CI,8CI);5-(3-Pyridinyl)proline;5-(3-Pyridyl)proline;Nornicotine-2-carboxylic acid

Chemical Property of Nornicotine-2-carboxylic Acid

Chemical Property:

• Vapor Pressure: 6.11E-07mmHg at 25°C
• Refractive Index: 1.566
• Boiling Point: 394.8°C at 760 mmHg
• PKA: 2.04±0.40(Predicted)
• Flash Point: 192.6°C
• PSA: 62.22000
• Density: 1.244g/cm³
• LogP: 1.28810
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 192.089877630
• Heavy Atom Count: 14
• Complexity: 220

Purity/Quality:

98%Min ^*data from raw suppliers

Nornicotine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC1C2=CN=CC=C2)C(=O)O
• Uses: Nornicotine-2-carboxylic acid is a Nicotine (N412420) derivative.

Technology Process of Nornicotine-2-carboxylic Acid

There total 6 articles about Nornicotine-2-carboxylic Acid 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: 67.0%

2',3'-dehydro-5'-carboxynornicotine (71136-44-2) → 5'-carboxynornicotine (3562-11-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 760 Torr;

DOI:10.1021/jo00391a066

Reference yield:

potassium nicotinate (16518-17-5) → 5'-carboxynornicotine (3562-11-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 52 percent / tetrahydrofuran / 20 h / Ambient temperature

2: 95 percent / 0.2 M aq. oxalic acid / 2 h / 90 °C

3: 1.) NH₃, 2.) NH₄Cl / 1.) MeOH, 4 deg C, 30 min, 2.) H₂O, MeOH, RT, 24 h

4: 69 percent / 10percent aq. KOH / 24 h / Heating

5: 67 percent / H₂ / 10percent Pd/C / aq. ethanol / 2 h / 760 Torr

With potassium hydroxide; ammonia; hydrogen; oxalic acid; ammonium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/jo00391a066

Reference yield:

5'-cyanomyosmine (109065-58-9) → 5'-carboxynornicotine (3562-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 10percent aq. KOH / 24 h / Heating

2: 67 percent / H₂ / 10percent Pd/C / aq. ethanol / 2 h / 760 Torr

With potassium hydroxide; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1021/jo00391a066

upstream raw materials:

2',3'-dehydro-5'-carboxynornicotine

potassium nicotinate

5'-cyanomyosmine

3-(1,3-dioxolan-2-yl)-1-(pyridin-3-yl)propan-1-one

Refernces