1130728-55-0

Basic information

• Product Name: 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid
• Synonyms: 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid
• CAS NO: 1130728-55-0
• Molecular Weight: 179.968
• Mol File: 1130728-55-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 96-98 °C
• Boiling Point: 340.5±52.0 °C(Predicted)
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid(1130728-55-0)
• EPA Substance Registry System: 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid(1130728-55-0)

Safety Data

• Hazardous Substances Data: 1130728-55-0(Hazardous Substances Data)

Usage

General Description

2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid is a chemical compound that belongs to the boronic acid family. It is a white to off-white crystalline powder that is soluble in organic solvents. 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid is commonly used in organic synthesis as a reagent for the Suzuki-Miyaura coupling reaction, which is a widely used method for the formation of carbon-carbon bonds. It is also utilized in the production of pharmaceuticals and agrochemicals, as well as in the synthesis of various fine chemicals. The presence of boronic acid functionality in this compound makes it a versatile building block for the construction of complex organic molecules.

Upstream product

• 1130728-51-6 (2,5-dimethyl-3,6-dimethoxylphenyl)boronic acid 
• 1130728-72-1 2-(3,6-dimethoxy-2,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 67975-91-1 2-chloro-4,4,5,5,-tetramethyl-1,3,2-dioxaboralane 

Downstream Products

• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 1262864-95-8 methyl 3-(1,3-dimethyl-2,5-dioxocyclohex-3-en-1-yl)-1H-indole-6-carboxylate 
• 1262864-92-5 6-((4-tert-butoxycarbonylamino)-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262864-91-4 6-(5-methoxy-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262865-12-2 6,6'-(1H-pyrrole-2,5-diyl)bis(2,6-dimethylcyclohex-2-ene-1,4-dione) 
• 1262864-97-0 2,6-dimethyl-6-(1H-pyrrol-2-yl)cyclohex-2-ene-1,4-dione 
• 1262864-94-7 6-(5-bromo-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262864-93-6 6-(5-fluoro-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262864-90-3 2,6-dimethyl-6-(7-methyl-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262864-89-0 2,6-dimethyl-6-(1-methyl-1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262865-03-1 6-(benzofuran-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262864-88-9 6-(1H-indol-3-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262864-96-9 6-(3,5-dimethyl-1H-pyrrol-2-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 
• 1262865-00-8 6-(5-chloro-4-methylthiophen-2-yl)-2,6-dimethylcyclohex-2-ene-1,4-dione 

Relevant articles and documents

Synthesis of functionalized alkyl substituted benzoquinones by Rh-catalyzed additions of boronic acids

A general synthetic route to γ-oxo alkyl or α-hydroxy benzyl 2-substituted benzoquinones has been developed through a one-pot Rh-catalyzed C-C bond formation/oxidative demethylation sequence from 2,5-dimethoxy aryl boronic acids and several electron deficient alkenes or aldehydes. The process allows rapid access to functionalized benzoquinones under very mild conditions and good yields. We disclose the first example of a Rh-catalyzed 1,4-addition reaction of benzoquinonyl boronic acid to methyl vinyl ketone and other conjugate acceptors, which allows the direct synthesis of 2-(γ-functionalized alkyl) substituted benzoquinones.

Control of the regio- and stereoselectivity in Diels-Alder reactions with quinone boronic acids

(Chemical Equation Presented) It all adds up: The dienophilic reactivity of 2-methyl-substituted quinones has been substantially increased by the introduction of a boronic acid substituent, which makes them equivalent to a highly reactive quinone. The Diels-Alder reactions of these quinones are followed by spontaneous and stereoselective protodeboronation to give the trans-fused adducts. The boron group is a temporal regiocontroller and leads to the uncommon meta adduct.