2,6-Pyridinedicarbonyl dichloride

Base Information

• Chemical Name: 2,6-Pyridinedicarbonyl dichloride
• CAS No.: 3739-94-4
• Molecular Formula: C7H3Cl2NO2
• Molecular Weight: 204.012
• Hs Code.: 29333990
• European Community (EC) Number: 223-125-4
• DSSTox Substance ID: DTXSID70958483
• Nikkaji Number: J187B
• Wikidata: Q72503890
• Mol file: 3739-94-4.mol

Synonyms:2,6-Pyridinedicarbonyl dichloride;3739-94-4;Pyridine-2,6-dicarbonyl dichloride;2,6-Pyridinedicarbonyl chloride;2,6-Pyridinedicarboxylic acid chloride;2,6-Pyridinedicarboxylicacidchloride;pyridine-2,6-dicarbonyl chloride;EINECS 223-125-4;Pyridine-2,6-dicarboxylic acid chloride;2,6-Pyridinedicarbony chloride;SCHEMBL321127;2,6-bis(chlorocarbonyl)pyridine;2,6-pyridine-dicarbonyl chloride;DTXSID70958483;MFCD00006289;AKOS015891493;2,6-Pyridinedicarbonyl dichloride, 97%;2,6-pyridine dicarboxylic acid dichloride;pyridine-2,6-dicarboxylic acid dichloride;1-(4,7,7-trimethylnorcaran-3-yl)ethanol;FT-0634996;E78148;A823625;W-111716

Chemical Property of 2,6-Pyridinedicarbonyl dichloride

Chemical Property:

• Appearance/Colour: white to brown crystalline powder, crystals
• Vapor Pressure: 0.00292mmHg at 25°C
• Melting Point: 56-58 °C(lit.)
• Refractive Index: 1.576
• Boiling Point: 284.74 °C at 760 mmHg
• PKA: -2.12±0.10(Predicted)
• Flash Point: 126.007 °C
• PSA: 47.03000
• Density: 1.506 g/cm³
• LogP: 1.83960
• Sensitive.: Moisture Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 202.9540837
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

2,6-Pyridinedicarbonyl dichloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=NC(=C1)C(=O)Cl)C(=O)Cl
• Uses: 2,6-Pyridinedicarboxylic acid chloride was used as the reagent during the synthesis of pyridine-based polyamido-polyester optically active macrocycles. It was used as starting reagent during the synthesis of pyridine-bridged 2,6-bis-carboxamide Schiff′s bases. It was used in the synthesis of N,N′-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide. 2,6-Pyridinedicarbonyl dichloride can be used as a starting material to synthesize: Pyridine-based polyamido-polyester optically active macrocycles by reacting with chiral diamine dihydrobromides. Pyridine-bridged 2,6-bis-carboxamide Schiff′s bases by treating with L-alanine or 2-methyl-alanine methyl esters. N,N′-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide by reacting with 1-pyrenemethylamine hydrochloride in the presence of a base.

Technology Process of 2,6-Pyridinedicarbonyl dichloride

There total 4 articles about 2,6-Pyridinedicarbonyl dichloride 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:

2,6-dimethylpyridine (108-48-5) → 2,6-Pyridinedicarbonyl dichloride (3739-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. KMnO₄

2: SOCl₂

With potassium permanganate; thionyl chloride;

DOI:10.1021/ja052129k

Reference yield:

6-(methoxycarbonyl)pyridine-2-carboxylic acid (7170-36-7) → 2,6-Pyridinedicarbonyl dichloride (3739-94-4)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 60 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1002/ejoc.200901479

Reference yield:

pyridine-2,6-dicarboxylic acid diamide (4663-97-2) → 2,6-Pyridinedicarbonyl dichloride (3739-94-4)

Guidance literature:

pyridine-2,6-dicarboxylic acid diamide; With thionyl chloride; In chloroform; at 0 ℃; for 5h; Reflux;

With phosphorus pentachloride; In chloroform; for 16h; Reflux;

DOI:10.1002/anie.201611067

upstream raw materials:

2,6-dimethylpyridine

6-(methoxycarbonyl)pyridine-2-carboxylic acid

pyridine-2,6-dicarboxylic acid diamide

Downstream raw materials:

2,6-bis(methoxycarbonyl)pyridine

diethyl-2,6-pyridinedicarbonyl ester

N²,N⁶-dibenzylpyridine-2,6-dicarboxamide

pyridine-2,6-dihydroxamic acid

Refernces

• 1、 Poh, Jian-Siang,Makai, Szabolcs,von Keutz, Timo,Tran, Duc N.,Battilocchio, Claudio,Pasau, Patrick,Ley, Steven V.. "Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines". supporting information. p. 1864 - 1868. Retrieved 2017/02/05.
• 2、 Macerata, Elena,Sansone, Francesco,Baldini, Laura,Ugozzoli, Franco,Brisach, Frederic,Haddaoui, Jaouad,Hubscher-Bruder, Veronique,Arnaud-Neu, Francoise,Mariani, Mario,Ungaro, Rocco,Casnati, Alessandro. "Calix[6]arene-picolinamide extractants for radioactive waste treatment: Effect of additional carboxy binding Sites in the pyridine 6-positions on complexation, extraction efficiency and An/Ln separation". experimental part. p. 2675 - 2686. Retrieved 2010/08/05.