2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid

Base Information

• Chemical Name: 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid
• CAS No.: 1130728-55-0
• Molecular Formula: C₈H₉BO₄
• Molecular Weight: 179.968
• Mol file: 1130728-55-0.mol

Synonyms:2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid

Chemical Property of 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid

Chemical Property:

• Melting Point: 96-98 °C
• Boiling Point: 340.5±52.0 °C(Predicted)
• Density: 1.28±0.1 g/cm3(Predicted)

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid

There total 3 articles about 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid 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: 97.0%

(2,5-dimethyl-3,6-dimethoxylphenyl)boronic acid (1130728-51-6) → 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid (1130728-55-0)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0°C;

DOI:10.1002/anie.200803428

Reference yield:

2-(3,6-dimethoxy-2,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1130728-72-1) → 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid (1130728-55-0) + 3,5-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-2,5-diene-1,4-dione (1130728-74-3)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; for 0.5h;

DOI:10.1039/c7ob00979h

Reference yield:

(2,5-dimethyl-3,6-dimethoxylphenyl)boronic acid (1130728-51-6) + 2-chloro-4,4,5,5,-tetramethyl-1,3,2-dioxaboralane (67975-91-1) → 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid (1130728-55-0) + 3,5-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-2,5-diene-1,4-dione (1130728-74-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pentane / 12 h / 20 °C / Inert atmosphere

2: ammonium cerium (IV) nitrate / acetonitrile; water / 0.5 h

With ammonium cerium (IV) nitrate; In water; acetonitrile; pentane;

DOI:10.1039/c7ob00979h

upstream raw materials:

(2,5-dimethyl-3,6-dimethoxylphenyl)boronic acid

2-chloro-4,4,5,5,-tetramethyl-1,3,2-dioxaboralane

2-(3,6-dimethoxy-2,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

2,6-dimethyl-1,4-benzoquinone

methyl 3-(1,3-dimethyl-2,5-dioxocyclohex-3-en-1-yl)-1H-indole-6-carboxylate

6-((4-tert-butoxycarbonylamino)-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione

6-(5-methoxy-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione

Refernces

• 1、 Veguillas, Marcos,Redondo, Maria C.,Garcia, Isabel,Ribagorda, Maria,Carmen Carreno. "Synthesis of benzo- And naphthoquinonyl boronic acids: Exploring the diels-alder reactivity". experimental part. p. 3707 - 3719. Retrieved 2010/07/13.