3-Bromo-2-phenylimidazo[1,2-a]pyridine

Base Information

• Chemical Name: 3-Bromo-2-phenylimidazo[1,2-a]pyridine
• CAS No.: 4044-95-5
• Molecular Formula: C13H9BrN2
• Molecular Weight: 273.132
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60355649
• Nikkaji Number: J3.629.678J
• Wikidata: Q82134667
• Mol file: 4044-95-5.mol

Synonyms:3-bromo-2-phenylimidazo[1,2-a]pyridine;4044-95-5;3-bromo-2-phenyl-imidazo[1,2-a]pyridine;MFCD00722629;Oprea1_480572;Oprea1_745171;SCHEMBL973109;IFLab1_006115;DTXSID60355649;HMS1429F21;AKOS001723521;CCG-122434;FT-0635109;A905352;F1563-0024

Chemical Property of 3-Bromo-2-phenylimidazo[1,2-a]pyridine

Chemical Property:

• Melting Point: 88-90 °C
• Refractive Index: 1.676
• PKA: 3.73±0.50(Predicted)
• PSA: 17.30000
• Density: 1.48 g/cm³
• LogP: 3.76380
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 271.99491
• Heavy Atom Count: 16
• Complexity: 240

Purity/Quality:

98%Min ^*data from raw suppliers

3-BROMO-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(N3C=CC=CC3=N2)Br

Technology Process of 3-Bromo-2-phenylimidazo[1,2-a]pyridine

There total 22 articles about 3-Bromo-2-phenylimidazo[1,2-a]pyridine 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: 98.0%

2-phenylimidazo[1,2-a]pyridine (4105-21-9) → 2-Phenyl-3-bromoimidazo<1,2-a>pyridine (4044-95-5)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 1.5h; regioselective reaction; Darkness;

DOI:10.1021/acs.jmedchem.0c02163

Reference yield: 92.0%

2-aminopyridine (504-29-0) + α-bromoacetophenone (70-11-1) → 2-Phenyl-3-bromoimidazo<1,2-a>pyridine (4044-95-5)

Guidance literature:

With tert.-butylhydroperoxide; In ethyl acetate; at 90 ℃; for 3h; Reagent/catalyst;

DOI:10.1039/c9ra06724h

Reference yield: 85.0%

2-phenyl-imidazo[1,2-a]pyridine; hydrobromide (3323-66-8) → 2-Phenyl-3-bromoimidazo<1,2-a>pyridine (4044-95-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; at 20 ℃; for 0.25h; Reagent/catalyst; Time; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0037-1611856

upstream raw materials:

3-nitroso-2-phenylimidazo<1,2-a>pyridine

2-phenylimidazo[1,2-a]pyridine

N-benzylidenepyridin-2-amine

Bromoform

Downstream raw materials:

3-nitro-2-(4'-nitrophenyl)imidazo[1,2-a]pyridine

3-bromo-2-(4'-nitrophenyl)imidazo[1,2-a]pyridine

2-phenyl-3-(pyridin-4-yl)imidazo[1,2-a]pyridine

2,3-diphenyl-1H-imidazo[1,2-a]pyridine

Refernces

• 1、 Rostrup, Frederik,Falk-Petersen, Christina B.,Harpsoe, Kasper,Buchleithner, Stine,Conforti, Irene,Jung, Sascha,Gloriam, David E.,Schirmeister, Tanja,Wellendorph, Petrine,Frolund, Bente. "Structural Determinants for the Mode of Action of Imidazopyridine DS2 at δ-Containing γ-Aminobutyric Acid Type A Receptors". . p. 4730 - 4743. Retrieved 2021/05/06.
• 2、 Balasubramanian, Sridhar,Kalari, Saradhi,Rode, Haridas B.. "Difluorinative-hydroxylation and C-3 functionalization (halogenation/SCN/NO) of imidazopyridine using Selectfluor as fluorine source or oxidant respectively". supporting information. . Retrieved 2021/04/15.