20039-93-4

Upstream product

• 106-44-5 p-cresol 
• 878-59-1 2,6-dibromo-4-methyl-4-nitro-2,5-cyclohexadien-1-one 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 

Downstream Products

• 61305-59-7 2,6-Dibrom-4-butyryloxy-4-methyl-cyclohexa-2,5-dienon 
• 61305-61-1 2,6-Dibrom-4-hexanoyloxy-4-methyl-cyclohexa-2,5-dienon 
• 61305-60-0 2,6-Dibrom-4-isobutyryloxy-4-methyl-cyclohexa-2,5-dienon 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 106-44-5 p-cresol 
• 1349842-59-6 2-bromo-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one 
• 1349842-81-4 tert-butyl (3,5-dibromo-1-methyl-4-oxocyclohexa-2,5-dien-1-yl) malonate 
• 21825-03-6 tetrabromobisphenol-F 
• 61305-89-3 3-Methyl-butyric acid 3,5-dibromo-1-methyl-4-oxo-cyclohexa-2,5-dienyl ester 
• 61305-58-6 2,6-Dibrom-4-methyl-4-propionyloxycyclohexa-2,5-dienon 
• 61305-54-2 4-acetoxy-2,6-dibromo-4-methyl-cyclohexa-2,5-dienone 

Relevant academic research and scientific papers

Reductive Aromatization of Quinols with B2pin2 as Deoxidizing Agent

We have demonstrated B2pin2 as superior deoxidizing agent for the reductive deoxygenation of quinol derivatives under basic conditions. A wide range of highly functionalized phenols were obtained in good yields including a complex drug molecule, which revealed the high functional group tolerance of this protocol.

Reactivity of hydroxy- and aquo(hydroxy)-λ3-iodane-crown ether complexes

We have designed a series of hydroxy(aryl)-λ3-iodane-[18] crown-6 complexes, prepared from the corresponding iodosylbenzene derivatives and superacids in the presence of [18]crown-6, and have investigated their reactivities in aqueous media. These activated iodosylbenzene monomers are all non-hygroscopic shelf-storable reagents, but they maintain high oxidizing ability in water. The complexes are effective for the oxidation of phenols, sulfides, olefins, silyl enol ethers, and alkyl(trifluoro)borates under mild conditions. Furthermore, hydroxy-λ3-iodane-[18]crown-6 complexes serve as efficient progenitors for the synthesis of diaryl-, vinyl-, and alkynyl-λ3-iodanes in water. Other less polar organic solvents, such as methanol, acetonitrile, and dichloromethane, are also usable in some cases. Aqua-friendly iodosylbenzene equivalents: Hydroxy- and aquo(hydroxy)-λ3-iodane-[18]crown-6 complexes (see graphic), readily prepared from commercial PhI(OAc)2 or PhIO, serve as excellent oxygen atom donors toward olefins, phenols, sulfides, and alkyl(trifluoro)borates. They also serve as progenitors for diaryl-, vinyl-, and alkynyl-λ3-iodane-[18]crown-6 complexes. These reactions can be carried out in aqueous media under mild reaction conditions.

A Simple and Efficient Procedure for the Preparation of p-Quinols by Hypervalent Iodine Oxidation of Phenols and Phenol Tripropylsilyl Ethers

Oxidation of para-substituted phenols with benzene (BTIB) in aqueous acetonitrile at 0 deg C gives p-quinols in moderate to good yields; higher yields are obtained when tripropylsilyl ethers of phenols are used.

The Nitration of Some Substituted 4-Methylphenols; X-Ray Crystal Structure of (Z)-3-Bromo-5-(bromonitromethylene)furan-2(5H)-one

The nitrations of 2-substituted 4-methyl-6-nitrophenols (1a), (1b) and (1c) give 6-substituted 3-methyl-2-nitro-1,4-benzoquinones (2a), (2b) and (2c).Similar reaction of 2,3-dibromo-4-methyl-6-nitrophenol (5) gives 2,3-dibromo-5-methyl-6-nitro-1,4-benzoquinone (7) and the 4-nitratocyclohexa-2,5-dienone (12).In contrast, 2,3,6-tribromo- (4a) and 2,6-dibromo- (4b) 4-methylphenols give 1,4-benzoquinones with loss of the methyl group.Lactone (18) was formed in the nitration of the 2,6-dibromophenol (4b) and its structure was determined by single-crystal X-ray analysis.