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

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)

Upstream product

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

Downstream Products

• 1262864-99-2 2,6-dimethyl-6-(thiophen-2-yl)cyclohex-2-ene-1,4-dione 
• 1262865-01-9 2,6-dimethyl-6-(5-methylfuran-2-yl)cyclohex-2-ene-1,4-dione 
• 1262865-02-0 6-(4,5-dimethylfuran-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 
• 1262864-96-9 6-(3,5-dimethyl-1H-pyrrol-2-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 
• 1262865-03-1 6-(benzofuran-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 
• 1262864-90-3 2,6-dimethyl-6-(7-methyl-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 
• 1262864-94-7 6-(5-bromo-1H-indol-3-yl)-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 
• 1262865-12-2 6,6'-(1H-pyrrole-2,5-diyl)bis(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 

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.

Synthesis of benzo- And naphthoquinonyl boronic acids: Exploring the diels-alder reactivity

Substituted 2-quinonyl boronic acids have been synthesised from 1,4-dimethoxy aromatic derivatives in two steps: regiocontrolled boronation and oxidative demethylation. The study of their dienophilic behaviour evidenced that the boron substituent significantly increases the reactivity and triggers an efficient domino process in which the Diels-Alder reaction was followed by a protodeboronation or dehydroboronation, depending on the substitution on both the quinone and diene partners. The boronic acid acts as a temporary controller, opening a direct access to trans-fused meta-regiosomeric adducts when 3-methyl-substi-tuted 2-quinonyl boronic acids react with dienes with a substituent at C-1. A particularly valuable synthetic result was obtained in the reaction between 3,6-dimethyl-2-quinonyl boronic acid and piperylene under an oxygen atmosphere; trans-fused 8a-hydroxy-2,4a,8trimethyl tetrahydronaphthoquinone was formed directly, in excellent yield and in a highly diastereoselective manner.

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.