4-(2-Pyridyl)benzaldehyde

Base Information

• Chemical Name: 4-(2-Pyridyl)benzaldehyde
• CAS No.: 127406-56-8
• Molecular Formula: C12H9NO
• Molecular Weight: 183.21
• Hs Code.: 29333990
• European Community (EC) Number: 627-948-3
• UNII: 65SW8X25MX
• DSSTox Substance ID: DTXSID90363914
• Nikkaji Number: J915.868E
• Wikidata: Q72504075
• ChEMBL ID: CHEMBL3542349
• Mol file: 127406-56-8.mol

Synonyms:4-pyridin-2-ylbenzaldehyde

Chemical Property of 4-(2-Pyridyl)benzaldehyde

Chemical Property:

• Appearance/Colour: acicular white solid
• Vapor Pressure: 8.62E-05mmHg at 25°C
• Melting Point: 51-53 ºC
• Refractive Index: 1.614
• Boiling Point: 340.4 ºC at 760 mmHg
• PKA: 3.97±0.25(Predicted)
• Flash Point: 167.6 ºC
• PSA: 29.96000
• Density: 1.147 g/cm³
• LogP: 2.56110
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in Chloroform
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 183.068413911
• Heavy Atom Count: 14
• Complexity: 185

Purity/Quality:

99% ^*data from raw suppliers

4-(2-Pyridinyl)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C2=CC=C(C=C2)C=O
• Uses: Reactive metabolite of atazanavir. Reactive metabolite of atazanavir. Atazanavir Impurity; Pyridinyl Benzaldehyde impurity

Technology Process of 4-(2-Pyridyl)benzaldehyde

There total 28 articles about 4-(2-Pyridyl)benzaldehyde 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: 100.0%

2-bromo-pyridine (109-04-6) + 4-formylphenylboronic acid, (87199-17-5) → 4-(2'-pyridyl)benzaldehyde (127406-56-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; for 8h; Reflux;

DOI:10.1002/ejoc.200701200

Reference yield: 100.0%

2-bromo-pyridine (109-04-6) + 1,1-dimethoxy-1-(4-bromophenyl)methane (24856-58-4) → 4-(2'-pyridyl)benzaldehyde (127406-56-8)

Guidance literature:

1,1-dimethoxy-1-(4-bromophenyl)methane; With iodine; magnesium; In tetrahydrofuran; at 30 - 35 ℃; for 2h;

2-bromo-pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc(II) chloride; In tetrahydrofuran; toluene; at 50 ℃; for 2.5h;

With hydrogenchloride; ammonia; water; more than 3 stages; Conversion of starting material;

Reference yield: 100.0%

2-chloropyridine (109-09-1) + 1,1-dimethoxy-1-(4-bromophenyl)methane (24856-58-4) → 4-(2'-pyridyl)benzaldehyde (127406-56-8)

Guidance literature:

1,1-dimethoxy-1-(4-bromophenyl)methane; With iodine; magnesium; In tetrahydrofuran; at 30 - 35 ℃; for 2.5h;

2-chloropyridine; With 1,4-di(diphenylphosphino)-butane; palladium diacetate; zinc(II) chloride; In tetrahydrofuran; at 70 ℃; for 3.5h; Conversion of starting material;

upstream raw materials:

2-(4-methylphenyl)pyridine

acetic anhydride

2-bromo-pyridine

4-bromo-benzaldehyde

Downstream raw materials:

2-(4-vinylphenyl)pyridine

4-(pyridin-2-yl)benzoic acid

2-(4-hydroxymethylphenyl)pyridine

2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester

Refernces

• 1、 Katari, Naresh K.,Prasad, Malavattu G.,Reddy, Pedavenkatagari N.,Vijayalakshmi, Chapala. "A scalable synthesis of biaryl unit of the HIV protease inhibitor atazanavir". . p. 68 - 72. Retrieved 2020.
• 2、 Zinser, Caroline M.,Nahra, Fady,Brill, Marcel,Meadows, Rebecca E.,Cordes, David B.,Slawin, Alexandra M. Z.,Nolan, Steven P.,Cazin, Catherine S. J.. "A simple synthetic entryway into palladium cross-coupling catalysis". . p. 7990 - 7993. Retrieved 2017.
• 3、 Cymerman-Craig,Loder. "-". . p. 100,101. Retrieved 1956.
• 4、 Chen, Qiaobin,Li, Chencheng,Wu, Jianglan,Zhao, Jiang. "Salicylaldehyde-based anion sensors featuring turn-on fluorescence, colorimetry, and the anti-counterfeiting application". . . Retrieved 2021.
• 5、 Muntaner, Jaime G.,Casarrubios, Luis,Sierra, Miguel A.. "Synthesis of new bioorganometallic Ir- and Rh-complexes having β-lactam containing ligands". . p. 286 - 297. Retrieved 2014.
• 6、 Jiang, Shimei,Li, Bao,Shang, Hongxing,Wang, Yufei. "Reversible luminescence "off-on" regulation based on tunable photodimerization: Via crystal-to-cocrystal transformation". supporting information. p. 734 - 741. Retrieved 2022/01/22.
• 7、 Bahadori, Maryam,Brykczyńska, Daria,Chatelain, Paul,Moran, Joseph,Muller, Cyprien,Rowley, Christopher N.,Sau, Abhijit. "Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides". supporting information. p. 25307 - 25312. Retrieved 2021/10/25.