2-Pyridinecarboxaldehyde

Base Information

• Chemical Name: 2-Pyridinecarboxaldehyde
• CAS No.: 1121-60-4
• Molecular Formula: C6H5NO
• Molecular Weight: 107.112
• Hs Code.: 29333999
• European Community (EC) Number: 214-333-6
• NSC Number: 8951
• UNII: KH86K8FHZ2
• DSSTox Substance ID: DTXSID1061522
• Nikkaji Number: J28.014C
• Wikipedia: Pyridine-2-carbaldehyde
• Wikidata: Q4596887
• Metabolomics Workbench ID: 66190
• ChEMBL ID: CHEMBL274794
• Mol file: 1121-60-4.mol

Synonyms:2-pyridinecarboxaldehyde;picolinaldehyde

Chemical Property of 2-Pyridinecarboxaldehyde

Chemical Property:

• Appearance/Colour: Yellow liquid
• Vapor Pressure: 0.906mmHg at 25°C
• Melting Point: -21--22 °C
• Refractive Index: n20/D 1.536(lit.)
• Boiling Point: 180.2 °C at 760 mmHg
• PKA: 3.8(at 20℃)
• Flash Point: 54.4 °C
• PSA: 29.96000
• Density: 1.135 g/cm³
• LogP: 0.89410
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: miscible
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 107.037113783
• Heavy Atom Count: 8
• Complexity: 82.6

Purity/Quality:

98% Min ^*data from raw suppliers

Picolinal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: Xn,Xi,N,T,F
• Statements: 10-22-36/37/38-51/53-46-43-34-23-52
• Safety Statements: 7-26-36-61-53-45-36/37/39-29-16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)C=O
• Uses: 2-Pyridinecarboxaldehyde has been used:To synthesize chitosan based bifunctionalized adsorbent.In the aldol addition reaction with pyruvate in the presence of 2-keto-3-deoxy-6-phosphogluconate aldolase (KDPG) catalyst to form (S)-4-hydroxy-2-keto-4-(2′-pyridyl)butyrate.In the condensation reaction with (S)-(?)-α-methylbenzylamine and (R)-(+)-α-methylbenzylamine to synthesize two chiral (S)-(?)- and (R)-(+)Schiff base compounds.It can also be combined with thiosemicarbazide to form 2-pyridinecarboxaldehyde thiosemicarbazone ligand (L) which can further complex with Ni(II) and Cu(II) salts (MX) to form [M(L)2X2] complexes.

Technology Process of 2-Pyridinecarboxaldehyde

There total 124 articles about 2-Pyridinecarboxaldehyde 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: 88.0%

3,6,6-Trimethyl-4-{[1-pyridin-2-yl-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester (117227-38-0) → pyridine-2-carbaldehyde (1121-60-4) + 2-Cyanopyridine (100-70-9,1232006-36-8)

Guidance literature:

With sodium methylate; In ethanol; for 3h; Product distribution; Heating;

Reference yield: 70.0%

2-Hydroxymethylpyridine (586-98-1) + diethylazodicarboxylate (1972-28-7,218603-74-8) → pyridine-2-carbaldehyde (1121-60-4) + diethyl hydrazodicarboxylate (4114-28-7)

Guidance literature:

With zinc dibromide; In toluene; for 2.5h; Reflux;

DOI:10.1016/j.tetlet.2009.01.080

Reference yield: 62.0%

pyridine-2-carboxylic acid amide (1452-77-3) → pyridine-2-carbaldehyde (1121-60-4) + 2-Hydroxymethylpyridine (586-98-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; for 0.583333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80441-5

upstream raw materials:

pyridine

N-methyl-N-phenylformamide

α-picoline

2-(Aminomethyl)pyridine

Downstream raw materials:

thieno[3,2-b]quinolizinylium; bromide

3-hydroxy-1,2-diphenyl-3-pyridin-2-yl-propan-1-one

2-pyridinaldazine

E-pyridine-2-carbaldehyde 2-pyridylhydrazone

Refernces

• 1、 Abramovitch et al.. "-". . p. 693. Retrieved 1974.
• 2、 Bunzen, Hana,Kolehmainen, Erkki. "In situ formation of steroidal supramolecular gels designed for drug release". . p. 3745 - 3759. Retrieved 2013.
• 3、 Mamaev,Gracheva. "-". . . Retrieved 1971.
• 4、 Leitis, L. Ya.,Skolmeistere, R. A.,Shimanskaya, M. V.. "MECHANISM OF THE CATALYTIC OXIDATION OF NITROGEN-CONTAINING METHYL-SUBSTITUTED HETEROCYCLES TO HETARYL ALDEHYDES". . p. 52 - 55. Retrieved 1987.
• 5、 Corriu, R. J. P.,Lanneau, G. F.,Perrot, M.. "THE ONE-POT CONVERSION OF CARBOXYLIC ACIDS TO ALDEHYDES VIA ACTIVATED SILYL CARBOXYLATES.". . p. 3941 - 3944. Retrieved 1987.
• 6、 Dai, Chenshu,Deng, Siqi,Zhu, Qiuhua,Tang, Xiaodong. "Synthesis of pyrrolo[1,2-: A] quinoxalines via copper or iron-catalyzed aerobic oxidative carboamination of sp3C-H bonds". . p. 44132 - 44135. Retrieved 2017.
• 7、 Fukuda, Naohiro,Kajiwara, Takeshi,Katou, Tomoaki,Majima, Keisuke,Ikemoto, Tomomi. "Convenient and eco-friendly method for the conversion of benzylic alcohols into aldehydes, ketones, and carboxylic acids using NaOCl without any additives in 1,2-dimethoxyethane". . p. 1438 - 1442. Retrieved 2013.
• 8、 McConnell, Anna J.,Haynes, Cally J. E.,Grommet, Angela B.,Aitchison, Catherine M.,Guilleme, Julia,Mikutis, Sigitas,Nitschke, Jonathan R.. "Orthogonal Stimuli Trigger Self-Assembly and Phase Transfer of FeII4L4 Cages and Cargoes". . p. 16952 - 16956. Retrieved 2018.
• 9、 Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan. "Selective oxidation of alkenes to carbonyls under mild conditions". supporting information. p. 5549 - 5555. Retrieved 2021/08/16.
• 10、 -. "Method for preparing aldehyde compounds by oxidative cleavage of carbon-carbon bonds of terminal alkene compounds". Paragraph 0073-0074; 0089-0090. . Retrieved 2021/06/06.