di-2-Pyridyl ketone

Base Information

• Chemical Name: di-2-Pyridyl ketone
• CAS No.: 19437-26-4
• Molecular Formula: C11H8N2O
• Molecular Weight: 184.197
• Hs Code.: 29339900
• European Community (EC) Number: 243-067-3
• NSC Number: 174057
• DSSTox Substance ID: DTXSID20173068
• Nikkaji Number: J149.899A
• Wikidata: Q72446851
• Mol file: 19437-26-4.mol

Synonyms:2,2'-dipyridyl ketone;2,2'-dipyridylketone

Chemical Property of di-2-Pyridyl ketone

Chemical Property:

• Appearance/Colour: beige to brown crystalline powder
• Vapor Pressure: 7.01E-05mmHg at 25°C
• Melting Point: 52-55 °C(lit.)
• Refractive Index: 1.593
• Boiling Point: 343.5 °C at 760 mmHg
• PKA: 2.30±0.10(Predicted)
• Flash Point: 165.7 °C
• PSA: 42.85000
• Density: 1.196 g/cm³
• LogP: 1.70760
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Low solubility in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.063662883
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

Di(2-pyridyl) ketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C(=O)C2=CC=CC=N2
• Uses: di-2-Pyridyl ketone has been used in the preparation of unusual {Ni(II)(3)Ln(III)(?-OR)(6)}(3+) complexes with a "star" topology. Its monoanionic form has been used in the synthesis of triangular Ni(2)M (M = lanthanide, Y) complexes. The Schiff base ligands derived from di-2-pyridyl ketone exhibit ant proliferative activity in SK-N-MC neuroepithelioma (cancer) cells. di-2-Pyridyl ketone has been used in the preparation of unusual {Ni(II)(3)Ln(III)(μ-OR)(6)}(3+) complexes with a "star" topology. Its monoanionic form has been used in the synthesis of triangular Ni(2)M (M = lanthanide, Y) complexes.

Technology Process of di-2-Pyridyl ketone

There total 29 articles about di-2-Pyridyl ketone 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: 69.0%

1,2-di(pyridin-2-yl)ethanone (59576-32-8) → 2,2'-dipyridyl ketone (19437-26-4)

Guidance literature:

With potassium phosphate; oxygen; copper diacetate; p-toluidine; sodium sulfate; In dimethyl sulfoxide; at 140 ℃; for 12h; Sealed tube;

DOI:10.1002/anie.201308785

Reference yield: 67.0%

2-pyridyllithium (17624-36-1) + ethyl N-methoxy-N-methylcarbamate (6919-62-6) → 2,2'-dipyridyl ketone (19437-26-4)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4039(00)99576-5

Reference yield: 66.0%

2-iodopyridine (5029-67-4) + 2-Picolinic acid (98-98-6) → 2,2'-dipyridyl ketone (19437-26-4)

Guidance literature:

2-Picolinic acid; With isopropylmagnesium bromide; In tetrahydrofuran; 2-methyltetrahydrofuran; at 20 ℃; Inert atmosphere; Cooling with ice;

2-iodopyridine; In tetrahydrofuran; 2-methyltetrahydrofuran; for 2h; Inert atmosphere;

With TurboGrignard; In tetrahydrofuran; 2-methyltetrahydrofuran; at 5 ℃; for 22h; Inert atmosphere;

DOI:10.1021/acs.joc.6b00194

upstream raw materials:

2-pyridyllithium

2-Cyanopyridine

ethyl-2-picolinate

bis(2-pyridyl)methane

Downstream raw materials:

bis(pyridin-2-yl)methanol

Bis[di(2-pyridyl)methyl]amine

(Di-pyridin-2-yl-methyl)-(di-pyridin-2-yl-methylene)-amine

di-2-pyridyl ketone oxime

Refernces

• 1、 Trovato et al.. "-". . p. 351,352,354. Retrieved 1976.
• 2、 Rao, G. Venkateswara,Swamy, B. Narayana,Kumar, P. Hareesh,Reddy, G. Chandrasekara. "Preferential reactivity of pyridylmagnesiumchloride with n,n-dialkyl arylamides over carbonitriles: Synthesis of 2-(Aroyl) pyridines". . p. 1835 - 1846. Retrieved 2009.
• 3、 Demkiw, Krystyna,Araki, Hirofumi,Elliott, Eric L.,Franklin, Christopher L.,Fukuzumi, Yoonjoo,Hicks, Frederick,Hosoi, Kazushi,Hukui, Tadashi,Ishimaru, Yoichiro,O'Brien, Erin,Omori, Yoshimasa,Mineno, Masahiro,Mizufune, Hideya,Sawada, Naotaka,Sawai, Yasuhiro,Zhu, Lei. "A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides". . p. 3447 - 3456. Retrieved 2016/05/19.