4-Imidazo[1,2-a]pyridin-2-ylbenzaldehyde

Base Information

• Chemical Name: 4-Imidazo[1,2-a]pyridin-2-ylbenzaldehyde
• CAS No.: 118000-48-9
• Molecular Formula: C₁₄H₁₀N₂O
• Molecular Weight: 222.246
• DSSTox Substance ID: DTXSID90356260
• Wikidata: Q82135511
• Mol file: 118000-48-9.mol

Synonyms:118000-48-9;4-imidazo[1,2-a]pyridin-2-ylbenzaldehyde;4-(IMIDAZO[1,2-A]PYRIDIN-2-YL)BENZALDEHYDE;SCHEMBL1428413;DTXSID90356260;MFCD05863346;AQ-776/42801096

Chemical Property of 4-Imidazo[1,2-a]pyridin-2-ylbenzaldehyde

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.079312947
• Heavy Atom Count: 17
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

4-(Imidazo[1,2-a]pyridin-2-yl)benzaldehyde 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NC(=CN2C=C1)C3=CC=C(C=C3)C=O

Technology Process of 4-Imidazo[1,2-a]pyridin-2-ylbenzaldehyde

There total 8 articles about 4-Imidazo[1,2-a]pyridin-2-ylbenzaldehyde 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: 89.0%

4-(H-imidazo[1,2-a]pyridin-2-yl)benzonitrile (55843-91-9) → 4-imidazo[1,2-a]pyridin-2-ylbenzaldehyde (118000-48-9)

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; for 1h; Ambient temperature;

DOI:10.1002/jhet.5570250119

Reference yield:

2-aminopyridine (504-29-0) → 4-imidazo[1,2-a]pyridin-2-ylbenzaldehyde (118000-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 48percent HBr / 1.) acetone, reflux, 12 h, 2.) MeOH, reflux, 2 h

2: 72 percent / dimethylformamide / 48 h / Heating

3: 1.) DIBAL, 2.) 10percent H₂SO₄, MeOH / 1.) toluene, RT, 3 h, 2.) toluene, RT, 40 min, overnight

With methanol; sulfuric acid; hydrogen bromide; diisobutylaluminium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jm9803368

Reference yield:

2-bromo-1-(4-iodophenyl)ethanone (31827-94-8) → 4-imidazo[1,2-a]pyridin-2-ylbenzaldehyde (118000-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 48percent HBr / 1.) acetone, reflux, 12 h, 2.) MeOH, reflux, 2 h

2: 72 percent / dimethylformamide / 48 h / Heating

3: 1.) DIBAL, 2.) 10percent H₂SO₄, MeOH / 1.) toluene, RT, 3 h, 2.) toluene, RT, 40 min, overnight

With methanol; sulfuric acid; hydrogen bromide; diisobutylaluminium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jm9803368

upstream raw materials:

4-(H-imidazo[1,2-a]pyridin-2-yl)benzonitrile

2-(4-iodophenyl)imidazo[1,2-α]pyridine

N,N-dimethyl-formamide

2-aminopyridine

Downstream raw materials:

4-(3-bromoimidazo[1,2-a]pyridin-2-yl)benzaldehyde

4-(5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridin-2-yl)-benzaldehyde

4-(3-Nitro-imidazo[1,2-a]pyridin-2-yl)-benzaldehyde

2-{4-[(E)-2-(4,5-Dihydro-thiazol-2-yl)-vinyl]-phenyl}-imidazo[1,2-a]pyridine

Refernces

• 1、 Sundberg, Richard J.,Biswas, Sujay,Murthi, Krishna Kumar,Rowe, Donna,McCall, John W.,Dzimianski, Michael T.. "Bis-cationic heteroaromatics as macrofilaricides: Synthesis of Bis- amidine and bis-guanylhydrazone derivatives of substituted imidazol[1,2- a]pyridines". . p. 4317 - 4328. Retrieved 2007/10/03.