2,3,5-Tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dien-1-one

Base Information

• Chemical Name: 2,3,5-Tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dien-1-one
• CAS No.: 105590-22-5
• Molecular Formula: C₇H₄Br₃NO₄
• Molecular Weight: 405.825
• DSSTox Substance ID: DTXSID20544355
• Mol file: 105590-22-5.mol

Synonyms:105590-22-5;2,3,5-Tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dien-1-one;DTXSID20544355

Chemical Property of 2,3,5-Tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dien-1-one

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 404.76700
• Heavy Atom Count: 15
• Complexity: 422

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(=C(C(=O)C(=C1Br)Br)[N+](=O)[O-])Br)O

Technology Process of 2,3,5-Tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dien-1-one

There total 3 articles about 2,3,5-Tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dien-1-one 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: 27.0%

2,3,5-tribromo-4-methyl-6-nitrophenol (105590-20-3) → 2,3,5-tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dienone (105590-22-5) + 2,3,5-tribromo-4-methyl-4-nitrato-6-nitrocyclohexa-2,5-dienone

Guidance literature:

With nitric acid; at 50 ℃; for 0.0833333h;

DOI:10.1071/CH9860059

Reference yield:

2,3,5-tribromo-4-methyl-4,6-dinitrocyclohexa-2,5-dienone (105590-21-4) → 2,3,5-tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dienone (105590-22-5)

Guidance literature:

With acetic acid; at 45 - 55 ℃; for 0.5h;

DOI:10.1071/CH9860059

Reference yield:

2,3,5-tribromo-4-methyl-6-nitrophenol (105590-20-3) → 2,3,5-tribromo-4-hydroxy-4-methyl-6-nitrocyclohexa-2,5-dienone (105590-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: fuming HNO₃ / acetic acid / 0.33 h / 20 °C

2: 700 mg / AcOH / 0.5 h / 45 - 55 °C

With nitric acid; acetic acid; In acetic acid;

DOI:10.1071/CH9860059

upstream raw materials:

2,3,5-tribromo-4-methyl-6-nitrophenol

2,3,5-tribromo-4-methyl-4,6-dinitrocyclohexa-2,5-dienone

Downstream raw materials:

2,3-dibromo-5-methyl-6-nitro-1,4-hydroquinone