[2,2':6',2''-Terpyridine]-4'-carbaldehyde

Base Information

• Chemical Name: [2,2':6',2''-Terpyridine]-4'-carbaldehyde
• CAS No.: 108295-45-0
• Molecular Formula: C16H11 N3 O
• Molecular Weight: 261.283
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70460975
• Nikkaji Number: J706.866B
• Wikidata: Q82285178
• Mol file: 108295-45-0.mol

Synonyms:108295-45-0;[2,2':6',2''-terpyridine]-4'-carbaldehyde;2,6-dipyridin-2-ylpyridine-4-carbaldehyde;[2,2':6',2''-Terpyridine]-4'-carboxaldehyde;2,2':6',2''-TERPYRIDINE-4'-CARBALDEHYDE;2,2':6',2''-Terpyridin-4'-carbaldehyd;YSCK0589;SCHEMBL14193770;DTXSID70460975;MFCD06796962;AS-76575;CS-0110276;2,2':6',2''-terpyridin-4'-carboxaldehyde;2,2':6',2''-Terpyridine-4'-carboxaldehyde;D94857;J-400136;[1~2~,2~2~:2~6~,3~2~-Terpyridine]-2~4~-carbaldehyde

Chemical Property of [2,2':6',2''-Terpyridine]-4'-carbaldehyde

Chemical Property:

• Boiling Point: 468.2°Cat760mmHg
• PKA: 4.24±0.22(Predicted)
• Flash Point: 235.6°C
• PSA: 55.74000
• Density: 1.236g/cm³
• LogP: 3.01810
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 261.090211983
• Heavy Atom Count: 20
• Complexity: 297

Purity/Quality:

98%min ^*data from raw suppliers

[2,2':6',2''-Terpyridine]-4'-carbaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C2=CC(=CC(=N2)C3=CC=CC=N3)C=O

Technology Process of [2,2':6',2''-Terpyridine]-4'-carbaldehyde

There total 10 articles about [2,2':6',2''-Terpyridine]-4'-carbaldehyde 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: 82.0%

2-tri-n-butylstannylpyridine (17997-47-6) + 2,6-Dibromopyridine-4-carbaldehyde (316800-46-1) → 4′-formyl-2,2′:6′2″-terpyridine (108295-45-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Inert atmosphere;

DOI:10.1021/jacs.7b05458

Reference yield: 57.0%

4'-methyl-2,2':6',2''-terpyridine (72036-41-0) → 4′-formyl-2,2′:6′2″-terpyridine (108295-45-0)

Guidance literature:

With iodine; tert.-butyl lithium; trifluoroacetic acid; In dimethyl sulfoxide; at 110 ℃; for 12h;

DOI:10.1021/ja00092a020

Reference yield:

4'-{[(Trifluoromethyl)sulfonyl]oxy}-2,2':6',2''-terpyridine (134653-69-3) → 4′-formyl-2,2′:6′2″-terpyridine (108295-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / LiCl / dimethylformamide / 3 h / 130 °C

2: 57 percent / I₂, CF₃COOH, tert-BuLi / dimethylsulfoxide / 12 h / 110 °C

With iodine; tert.-butyl lithium; trifluoroacetic acid; lithium chloride; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00092a020

upstream raw materials:

4'-methyl-2,2':6',2''-terpyridine

2-tri-n-butylstannylpyridine

2,6-Dibromopyridine-4-carbaldehyde

2,6-dibromo-4-(hydroxymethyl)pyridine

Downstream raw materials:

2,2':6,2''-terpyridine

4'-phenyl-2,2':6',2-terpyridine

(3S,5S)-1-[(benzyloxy)carbonyl]-3-({[2,6-bis-(pyridin-2-yl)pyridin-4-yl]methyl}amino)-5-[(tert-butoxy)-carbonyl]pyrrolidine-3-carboxylic acid

7-benzyl 8-tert-butyl (5S,8S)-1-{[2,6-bis-(pyridin-2-yl)pyridin-4-yl]methyl}-2,4-dioxo-3-phenyl-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylate

Refernces

• 1、 Korom, Sa?a,Ballester, Pablo. "Attachment of a RuII Complex to a Self-Folding Hexaamide Deep Cavitand". supporting information. p. 12109 - 12112. Retrieved 2017/09/12.
• 2、 Flamigni, Lucia,Barigelletti, Francesco,Armaroli, Nicola,Collin, Jean-Paul,Sauvage, Jean-Pierre,Williams, J.A. Gareth. "Photoinduced processes in highly coupled multicomponent arrays based on a ruthenium(II)bis(terpyridine) complex and porphyrins". . p. 1744 - 1754. Retrieved 2007/10/03.