4,4'-Dimethyl-6,6'-diacetyl-2,2'-bipyridine

Base Information

• Chemical Name: 4,4'-Dimethyl-6,6'-diacetyl-2,2'-bipyridine
• CAS No.: 117873-75-3
• Molecular Formula: C₁₆H₁₆N₂O₄
• Molecular Weight: 300.314
• DSSTox Substance ID: DTXSID20702236
• Wikidata: Q82634088
• Mol file: 117873-75-3.mol

Synonyms:4,4'-DIMETHYL-6,6'-DIACETYL-2,2'-BIPYRIDINE;117873-75-3;DTXSID20702236;KFJXHGRSRFBXLS-UHFFFAOYSA-N;J-400506;1,1'-(4,4'-Dimethyl[2,2'-bipyridine]-6,6'-diyl)di(ethan-1-one)

Chemical Property of 4,4'-Dimethyl-6,6'-diacetyl-2,2'-bipyridine

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 268.121177757
• Heavy Atom Count: 20
• Complexity: 347

Purity/Quality:

4,4'-DIMETHYL-6,6'-DIACETYL-2,2'-BIPYRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=NC(=C1)C(=O)C)C2=NC(=CC(=C2)C)C(=O)C

Technology Process of 4,4'-Dimethyl-6,6'-diacetyl-2,2'-bipyridine

There total 6 articles about 4,4'-Dimethyl-6,6'-diacetyl-2,2'-bipyridine 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:

2,6-Dibromopyridine (626-05-1) → 6,6'-Diacetyl-4,4'-dimethoxy-2,2'-bipyridin (117873-75-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / 35percent H₂O₂ / trifluoroacetic acid / 3 h / 80 °C

2: 85 percent / oleum, HNO₃ / 2 h / 90 °C

3: 1.) acetyl bromide; 2.) PBr₃ / 1.) glacial acetic acid, 2 h, 80 deg C; 2.) CHCl₃, 1 h, RT; 2 d, reflux

4: 66 percent / methanol / 2.5 h / Heating

5: 1.) tBuOK, n-BuLi; 2.) CuCl₂ / 1.) ether, hexane; 2.) -90 deg C to -50 deg C

6: 1.) tBuOK, n-BuLi; 3.) 6N HCl / 1.) THF, hexane, -80 deg C to -75 deg C, 1 h; 2.) 2 h, -80 deg C to -30 deg C

With hydrogenchloride; n-butyllithium; Acetyl bromide; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; nitric acid; phosphorus tribromide; copper dichloride; In methanol; trifluoroacetic acid;

Reference yield:

2,4,6-tribromopyridine (2408-70-0) → 6,6'-Diacetyl-4,4'-dimethoxy-2,2'-bipyridin (117873-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / methanol / 2.5 h / Heating

2: 1.) tBuOK, n-BuLi; 2.) CuCl₂ / 1.) ether, hexane; 2.) -90 deg C to -50 deg C

3: 1.) tBuOK, n-BuLi; 3.) 6N HCl / 1.) THF, hexane, -80 deg C to -75 deg C, 1 h; 2.) 2 h, -80 deg C to -30 deg C

With hydrogenchloride; n-butyllithium; potassium tert-butylate; copper dichloride; In methanol;

Reference yield:

2,6-dibromopyridin N-oxide (25373-69-7) → 6,6'-Diacetyl-4,4'-dimethoxy-2,2'-bipyridin (117873-75-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / oleum, HNO₃ / 2 h / 90 °C

2: 1.) acetyl bromide; 2.) PBr₃ / 1.) glacial acetic acid, 2 h, 80 deg C; 2.) CHCl₃, 1 h, RT; 2 d, reflux

3: 66 percent / methanol / 2.5 h / Heating

4: 1.) tBuOK, n-BuLi; 2.) CuCl₂ / 1.) ether, hexane; 2.) -90 deg C to -50 deg C

5: 1.) tBuOK, n-BuLi; 3.) 6N HCl / 1.) THF, hexane, -80 deg C to -75 deg C, 1 h; 2.) 2 h, -80 deg C to -30 deg C

With hydrogenchloride; n-butyllithium; Acetyl bromide; sulfuric acid; potassium tert-butylate; nitric acid; phosphorus tribromide; copper dichloride; In methanol;

upstream raw materials:

N,N-dimethyl acetamide

6,6’-dibromo-4,4’-dimethoxy-2,2’-bipyridine

2,6-Dibromopyridine

2,4,6-tribromopyridine