Isonicotinaldehyde, azine

Base Information

• Chemical Name: Isonicotinaldehyde, azine
• CAS No.: 6957-22-8
• Molecular Formula: C12H10 N4
• Molecular Weight: 210.238
• Hs Code.: 2933990090
• European Community (EC) Number: 230-145-7
• ChEMBL ID: CHEMBL3208921
• Mol file: 6957-22-8.mol

Synonyms:Isonicotinaldehyde, azine;6957-22-8;197644-96-5;4-Pyridinecarboxaldehyde,2-(4-pyridinylmethylene)hydrazone;(1E,2E)-1,2-Bis(pyridin-4-ylmethylene)hydrazine;1,2-Bis(pyridin-4-ylmethylene)hydrazine;Isonicotinaldehyde (4-pyridylmethylene)hydrazone;EINECS 230-145-7;(E)-1-pyridin-4-yl-N-[(E)-pyridin-4-ylmethylideneamino]methanimine;4-[(1E)-[(E)-2-[(pyridin-4-yl)methylidene]hydrazin-1-ylidene]methyl]pyridine;4-[(1E)-[(E)-2-(pyridin-4-ylmethylidene)hydrazin-1-ylidene]methyl]pyridine;4-Pyridinecarboxaldehyde, (4-pyridinylmethylene)hydrazone;4-{[2-(pyridin-4-ylmethylidene)hydrazin-1-ylidene]methyl}pyridine;MLS001241038;SCHEMBL9966011;CHEMBL3208921;XLLIUDMGQNPRJS-KAVGSWPWSA-N;NSC 66165;AKOS015994020;HF-0025;NCGC00247378-01;AS-81882;SMR000841156;CS-0170044;CS-0379172;Z204610866;1-pyridin-4-yl-N-(pyridin-4-ylmethylideneamino)methanimine;Isonicotinaldehyde [(E)-4-pyridinylmethylidene]hydrazone #

Chemical Property of Isonicotinaldehyde, azine

Chemical Property:

• Vapor Pressure: 3.97E-05mmHg at 25°C
• Melting Point: 178 °C
• Boiling Point: 362.7°C at 760 mmHg
• PKA: 4.68±0.50(Predicted)
• Flash Point: 173.1°C
• PSA: 50.50000
• Density: 1.12g/cm³
• LogP: 1.92960
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 210.090546336
• Heavy Atom Count: 16
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

4-[(1E)-[(E)-2-(Pyridin-4-ylmethylidene)hydrazin-1-ylidene]methyl]pyridine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC=C1C=NN=CC2=CC=NC=C2
• Isomeric SMILES: C1=CN=CC=C1/C=N/N=C/C2=CC=NC=C2

Technology Process of Isonicotinaldehyde, azine

There total 9 articles about Isonicotinaldehyde, azine 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: 92.0%

pyridine-4-carbaldehyde (872-85-5) → 4-pyridinealdazine (6957-22-8)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 0.333333h;

DOI:10.1039/c7dt03667a

Reference yield: 89.0%

Pyridine-4-carboxaldehyde hydrazone (51832-68-9) → (1E,2E)-1,2-bis(pyridin-4-ylmethylene)hydrazine (6957-22-8)

Guidance literature:

With hydrogenchloride; In ethanol; for 0.0833333h;

DOI:10.1021/je00031a035

Reference yield: 75.0%

pyridine-4-carbaldehyde (872-85-5) → (1E,2E)-1,2-bis(pyridin-4-ylmethylene)hydrazine (6957-22-8)

Guidance literature:

With hydrazine hydrate; In ethanol; for 0.333333h;

DOI:10.1039/b500698h

upstream raw materials:

pyridine-4-carbaldehyde

Pyridine-4-carboxaldehyde hydrazone

N′-(pyridin-4-yl-benzylidene)-4-methylbenzenesulfonohydrazide

N'-[1-Pyridin-4-yl-meth-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester

Refernces

A novel approach for highly regio- and stereoselective synthesis of (Z)-3-methyleneisoindoline-1-ones in aqueous micellar medium

10.1016/j.tetlet.2012.10.001

The study presents an environmentally benign and operationally simple method for the regio- and stereoselective synthesis of (Z)-3-methyleneisoindolinones in an aqueous micellar medium. The key chemicals involved include 2-iodo-N-phenyl-benzamides and terminal alkynes as starting materials. The reaction is catalyzed by Pd(CH3CN)Cl2 in the presence of 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene as a ligand, and cetyltrimethylammonium bromide (CTAB) as a surfactant to form micelles, which enhance the solubility and reaction efficiency. The use of DBU as a base is crucial for achieving high yields. This Cu-free domino Sonogashira reaction followed by 5-exo-dig cyclization under aerobic conditions allows for the synthesis of a library of (Z)-3-methyleneisoindolinones with high yields and short reaction times, highlighting the eco-friendly and efficient nature of the protocol.