Picolinamide

Base Information

• Chemical Name: Picolinamide
• CAS No.: 1452-77-3
• Deprecated CAS: 39194-75-7
• Molecular Formula: C6H6N2O
• Molecular Weight: 122.126
• Hs Code.: 29333990
• European Community (EC) Number: 215-921-5
• NSC Number: 524473
• UNII: I3550CCL59
• DSSTox Substance ID: DTXSID4061703
• Nikkaji Number: J27.993E
• Wikidata: Q27107933
• Metabolomics Workbench ID: 53364
• Mol file: 1452-77-3.mol

Synonyms:picolinamide

Chemical Property of Picolinamide

Chemical Property:

• Vapor Pressure: 2.95E-11mmHg at 25°C
• Melting Point: 110°C (dec.)(lit.)
• Refractive Index: 1.616
• Boiling Point: 334.4 °C at 760 mmHg
• PKA: pK1: 2.10(+1) (20°C)
• Flash Point: 156 °C
• PSA: 55.98000
• Density: 1.204 g/cm³
• LogP: 0.88080
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.048012819
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

98% ^*data from raw suppliers

Picolinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C(=O)N
• General Description: PYRIDINE-2-CARBOXAMIDE (also known as picolinamide) is a versatile ligand used in the synthesis of organometallic complexes, particularly in anticancer research, where it binds to rhodium, iridium, and ruthenium centers to form stable, cytotoxic species. It also serves as a key component in chiral Lewis base catalysts for enantioselective reactions, such as the hydrosilylation of α,β-unsaturated ketones, demonstrating its utility in both medicinal chemistry and asymmetric synthesis.

Technology Process of Picolinamide

There total 95 articles about Picolinamide 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: 84.0%

2-Cyanopyridine (100-70-9,1232006-36-8) + 1-dodecyl alcohol (112-53-8) → pyridine-2-carboxylic acid amide (1452-77-3) + dodecyl benzoate (2915-72-2)

Guidance literature:

With cerium(IV) oxide; water; at 160 ℃; for 36h; Inert atmosphere;

DOI:10.1021/acscatal.6b00272

Reference yield: 61.0%

2-hydroxyiminomethyl-pyridine (2110-14-7) → 2-Cyanopyridine (100-70-9,1232006-36-8) + pyridine-2-carboxylic acid amide (1452-77-3)

Guidance literature:

With cerium(IV) oxide; In o-xylene; at 160 ℃; for 6h; Dean-Stark; Inert atmosphere;

DOI:10.1021/acscatal.6b00272

Reference yield: 60.0%

2-Hydroxymethylpyridine (586-98-1) → 2-Cyanopyridine (100-70-9,1232006-36-8) + pyridine-2-carboxylic acid amide (1452-77-3)

Guidance literature:

With tert.-butylhydroperoxide; tetraethylammonium iodide; ammonium bicarbonate; In acetonitrile; at 70 ℃; for 22h;

DOI:10.1039/c3ob42037j

upstream raw materials:

2-bromo-pyridine

potassium cyanide

cyanomethyl 2-pyridinecarboxylate

pyridine-2-carbaldehyde

Downstream raw materials:

N-(hydroxymethyl)picolinamide

2-pyridinecarboxylic acid N-oxide

2-pyridinecarboxamide 1-oxide

α-picoline

Refernces

Rhodium, iridium, and ruthenium half-sandwich picolinamide complexes as anticancer agents

10.1021/ic401529u

This study investigated the potential of rhodium, iridium, and ruthenium half-sandwich complexes containing (N,N)-bound picolinamide ligands as anticancer agents. Picolinamide plays a crucial role as a ligand in the synthesis of rhodium, iridium, and ruthenium half-sandwich complexes. The picolinamide ligand binds to the metal center (N,N) to form a neutral 18-electron species. This study aimed to optimize the design and potency of these organometallic complexes by exploring the effects of different halide substituents on their anticancer activities. The presence, position, and number of halides significantly affected the IC50 values ??of the complexes. Notably, one ruthenium complex (compound 12) was more cytotoxic than cisplatin against HT-29 and MCF-7 cells under both normoxic and hypoxic conditions, making it a promising candidate for in vivo studies. The study also explored the inhibitory effects of the complexes on thioredoxin reductase 1 (Trx-R) and found that the iridium and rhodium complexes were potent inhibitors, while the ruthenium complex was not, suggesting a different mechanism of action. Future work will focus on further in vivo studies and evaluating the effects of the compounds on normal tissues.

Enantioselective conjugate hydrosilylation of α,β-unsaturated ketones

10.1039/c9ra01180c

The research focuses on the enantioselective conjugate hydrosilylation of β,β-disubstituted α,β-unsaturated ketones, utilizing chiral picolinamide–sulfonate Lewis base catalysts. The main objective was to synthesize various chiral ketones with a chiral center at the β-position, which are crucial intermediates for natural products and chiral drugs. The experiments involved screening different chiral Lewis base catalysts for the hydrosilylation of (E)-1,3-diphenylbut-2-en-1-one in acetonitrile at 0°C, and optimizing reaction conditions such as solvents and temperature to achieve the best yield and enantioselectivity. The reactants included α,β-unsaturated ketones, trichlorosilane, and the selected catalyst 2f. The analyses used to determine the success of the reactions and the enantiomeric excess (ee) of the products were chiral high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy.