Imidazo[1,5-a]pyridine-3(2H)-thione

Base Information

• Chemical Name: Imidazo[1,5-a]pyridine-3(2H)-thione
• CAS No.: 76259-00-2
• Molecular Formula: C7H6 N2 S
• Molecular Weight: 150.2
• Mol file: 76259-00-2.mol

Synonyms:2,3-Dihydroimidazo[1,5a]pyridine-3-thione;Imidazo[1,5-a]pyridine-3-thiol

Chemical Property of Imidazo[1,5-a]pyridine-3(2H)-thione

Chemical Property:

• Vapor Pressure: 0.0011mmHg at 25°C
• Melting Point: 169 °C(Solv: ethanol (64-17-5))
• Boiling Point: 300.7°C at 760 mmHg
• PKA: 9.57±0.20(Predicted)
• Flash Point: 135.6°C
• Density: 1.41g/cm³

Purity/Quality:

99% ^*data from raw suppliers

2H,3H-imidazo[1,5-a]pyridine-3-thione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Imidazo[1,5-a]pyridine-3(2H)-thione

There total 2 articles about Imidazo[1,5-a]pyridine-3(2H)-thione 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: 81.0%

2-(Aminomethyl)pyridine (3731-51-9) + phenyl isothiocyanate (103-72-0) → imidazo[1,5-a]pyridine-3-thiol (76259-00-2)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 145 ℃; for 3h; Cooling with ice;

Reference yield: 60.0%

N-phenyl-N'-(pyridin-2-ylmethyl)thiourea (75160-54-2) → dihydro-2,3 imidazo<1,5-a>pyridinethione-3 (76259-00-2)

Guidance literature:

In toluene; for 24h; Heating;

Reference yield: 95.0%

dihydro-2,3 imidazo<1,5-a>pyridinethione-3 (76259-00-2) + benzaldehyde (100-52-7) + methylamine (74-89-5) → 1-Methyl-5-phenyl-4-pyridin-2-yl-imidazolidine-2-thione (345218-31-7)

Guidance literature:

toluene-4-sulfonic acid; In ethanol; Heating; Cis:trans ratio 2:1;

DOI:10.1016/S0040-4039(01)81990-0

upstream raw materials:

2-(Aminomethyl)pyridine

phenyl isothiocyanate

N-phenyl-N'-(pyridin-2-ylmethyl)thiourea

Downstream raw materials:

(nitro-4 benzyl)thio-3 imidazo<1,5-a>pyridine

[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester

1-Methyl-5-phenyl-4-pyridin-2-yl-imidazolidine-2-thione

1-(4-Methoxy-phenyl)-5,5-dimethyl-4-pyridin-2-yl-imidazolidine-2-thione

Refernces

• 1、 Mihorianu, Monica,Franz, M Heiko,Jones, Peter G,Freytag, Matthias,Kelter, Gerhard,Fiebig, Heinz-Herbert,Tamm, Matthias,Neda, Ion. "N-Heterocyclic carbenes derived from imidazo-[1,5-a]pyridines related to natural products: synthesis, structure and potential biological activity of some corresponding gold(I) and silver(I) complexes". . p. 581 - 589. Retrieved 2016/07/16.
• 2、 Bourdais, Jacques,Rajniakova, Olga,Povazanec, Frantisek. "Azines polycycliques. (IV). Synthese de derives sulfures en -3 de l'imidazolpyridine". . p. 1351 - 1353. Retrieved 2007/10/02.