Imidazo[1,5-a]pyridine

Base Information

• Chemical Name: Imidazo[1,5-a]pyridine
• CAS No.: 274-47-5
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 2933599590
• European Community (EC) Number: 819-899-3
• NSC Number: 119858
• DSSTox Substance ID: DTXSID20297970
• Nikkaji Number: J150.426F
• Wikidata: Q72482496
• ChEMBL ID: CHEMBL4441336
• Mol file: 274-47-5.mol

Synonyms:imidazo(1,5-a)pyridine

Chemical Property of Imidazo[1,5-a]pyridine

Chemical Property:

• Melting Point: 52.0 to 57.0 °C
• Refractive Index: 1.628
• Boiling Point: 120-125 °C(Press: 3 Torr)
• PKA: 7.50±0.30(Predicted)
• PSA: 17.30000
• Density: 1.14 g/cm³
• LogP: 1.33430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

Imidazo[1,5-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=CN=CN2C=C1

Technology Process of Imidazo[1,5-a]pyridine

There total 8 articles about Imidazo[1,5-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: 77.0%

pyridine-2-carbaldehyde (1121-60-4) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → imidazo[1,5-a]pyridine (274-47-5)

Guidance literature:

With ammonium acetate; acetic acid; at 20 ℃; for 3h;

DOI:10.1039/c8ob02705f

Reference yield: 76.0%

2-(Aminomethyl)pyridine (3731-51-9) + formic acid (64-18-6) → imidazo[1,5-a]pyridine (274-47-5)

Guidance literature:

2-(Aminomethyl)pyridine; formic acid; at 100 ℃;

With trichlorophosphate; In toluene; at 120 ℃;

DOI:10.1039/d1ra05417a

Reference yield: 62.0%

2-(Aminomethyl)pyridine (3731-51-9) + nitromethane (75-52-5) → imidazo[1,5-a]pyridine (274-47-5)

Guidance literature:

With phosphoric acid; at 160 ℃; for 2h;

DOI:10.3762/BJOC.16.239

upstream raw materials:

N-((pyridin-2-yl)methyl)formamide

2-(Aminomethyl)pyridine

chloroform

pyridine-2-carbaldehyde

Downstream raw materials:

(2,6-Dichloro-phenyl)-imidazo[1,5-a]pyridin-1-yl-methanone

1-nitroimidazo<1,5-a>pyridine

1,3-Dinitro-imidazo[1,5-a]pyridine

Refernces

• 1、 Dinh, Long P.,Harris, Nekoda W.,Jacoby, Seth A.,Semsey, Rebecca Y.,Swann, William A.,Tran, Ryan Q.,Williamson, Savannah N.,Yet, Larry. "Synthesis of 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions". . p. 28347 - 28351. Retrieved 2021/09/15.
• 2、 Singh, Dharmender,Sharma, Shubham,Kumar, Mukesh,Kaur, Inderpreet,Shankar, Ravi,Pandey, Satyendra Kumar,Singh, Virender. "An AcOH-mediated metal free approach towards the synthesis of bis-carbolines and imidazopyridoindole derivatives and assessment of their photophysical properties". supporting information. p. 835 - 844. Retrieved 2019/02/01.