1967-89-1

Usage

Synonym

DCMTB

Physical state

White crystalline solid

Solubility

Insoluble in water

Melting point

High

Industrial applications

Used as a biocide and fungicide in adhesives, plastics, and coatings production

Effectiveness

Inhibits growth of bacteria, fungi, and algae

Purpose

Provides long-term preservation and protection against microbial contamination in products

Additional properties

Investigated for potential insecticidal properties

Hazards

Harmful if ingested or inhaled, causes skin and eye irritation upon contact

Safety precautions

Proper handling and safety measures necessary when working with DCMTB

Upstream product

• 95-93-2 1,2,4,5-tetramethylbenzene 
• 31604-30-5 1,2,4,5-tetrabromo-3,6-dichlorobenzene 
• 77-78-1 dimethyl sulfate 
• 26976-92-1 1,2,4,5-tetramethyl-3,6-dihydrobenzene 

Downstream Products

• 499154-47-1 2,5-dichloro-3,6-dimethyl-benzene-1,4-dicarbaldehyde 
• 92291-79-7 3,6-Dichlor-benzol-1,2,4,5-tetracarbonsaeure-tetramethylester (Dichlor-pyromellitsaeure-tetramethylester) 
• 80120-38-3 ethyl (2,3,5,6-tetramethylphenyl)-2-oxoacetate 
• 7072-01-7 2,3,5,6-tetramethyl-1,4-benzenedicarboxaldehyde 
• 17432-37-0 2,3,5,6-tetramethylbenzaldehyde 
• 21021-54-5 dichloropyromellitic acid 

Relevant academic research and scientific papers

Chlorination of aromatics with trichloroisocyanuric acid (TCICA) in bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf]: An economical, green protocol for the synthesis of chloroarenes

A survey study on electrophilic chlorination of aromatics with trichloroisocyanuric acid (TCICA) in Bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf] is reported. The reactions are performed under very mild conditions (at ～50°C) and give good to excellent yields, depending on the substrates. Chemoselectivity for mono- v. dichlorination can be tuned by changing the arene-to-TCICA ratio and the reaction time. The survey study and competitive experiments suggest that triprotonated/protosolvated TCICA is a selective/moderately reactive transfer-chlorination electrophile. Density functional theory was used as guide to obtain further insight into the nature of the chlorination electrophile and the transfer-chlorination step. CSIRO 2007.

Chlorination of aromatic compounds with chlorous acid under non-aqueous conditions

The non-aqueous solution of chlorous acid is a versatile chlorinating agent for aromatic compounds, e.g. alkylbenzenes, anisoles, and acetanililides. It is also an effective chlorine-substitute for the conversion of aryl bromides into aryl chlorides under mild conditions. The stoichiometry of the chlorination reaction is ArH+3HOClO→ArCl+2ClO2+2H2O, and the mode of dissociation of chlorous acid in dichloromethanc is 3HOClO→HOCl+2ClO2+H2O.

Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports

Pulverization-activation method was employed to accelerate solid-state organic reactions. Crushing and grinding of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene and organic substrates in the absence of a solvent brought about smooth and rapid reactions to give halogenated and/or oxidized products in good yields. Various sulfides were smoothly converted to sulfonyl chlorides in one step in excellent yields. The surface of silica gel activated by pulverization serves as a reaction field on which reagent molecules can effectively encounter with each other.

Mild chlorination of aromatic compounds with tin(IV) chloride and lead tetraacetate

SnCl4/Pb(OAc)4 acts as a safe source of Cl2 for the chlorination of aromatic compounds. A variety of aromatic compounds are effectively chlorinated with SnCl4/Pb(OAc)4 under mild conditions. The mixture is a selective chlorinating agent, particularly with polyalkylbenzenes, polycyclic aromatic compounds and anisoles.

Amino-, Aminophenoxy- and Aminobenzoyl Derivatives of Durene

Various durene derivatives have been prepared including 4-hydroxy-, 4-aryloxy- and 4-aroyl- derivatives of 2,3,5,6-tetramethylaniline and bis(4-aminophenoxy)- and bis-(4-aminobenzoyl)durene.

Solid-State Organic Reactions Proceeding by Pulverization of Inorganic Solid-Supports. Reactions of Iodosobenzene with Unsaturated Hydrocarbons on Acid-Treated Silica Gel

Pulverization of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene, and alkenes or an alkyne in the absence of a solvent brings about smooth and rapid reaction to give halogenated or oxidized products in good yields.

Halogenation Using Quaternary Ammonium Polyhalides. XIX. Aromatic Chlorination of Arenes with Benzyltrimethylammonium Tetrachloroiodate

The reaction of arenes with a calculated amount of benzyltrimethylammonium tetrachloroiodate in acetic acid at room temperature or at 70 deg C gave nuclear chloro-substituted arenes in fairly good yields.

AN IMPROVED SYNTHESIS OF DIHALOPYROMELLITIC ACID

A practical molar scale synthesis of the commercially unavailable dichloro- and dibromopyromellitic acids are described in detail.

OXIDATIVE CHLORINATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS

Mixture of the chlorides and nitrates of alkali metals in aqueous trifluoroacetic acid can be used for the selective oxidative chlorination of benzene, halogenobenzenes, toluene, and p-toluic acid with preparative yields.By variation of the water content of the solvent and the nitrate-chloride ratio it is possible to suppress the nitration side reaction.In the presence of oxygen or air alkali-metal nitrites can also be used as oxidizing agents in this process.The chlorinating agent in these systems is molecular chlorine, as confirmed by a comparative study of the reactions of two groups of potential chlorinating agents (nitrosyl chloride and nitryl chloride) under these conditions.The reactions of naphthalene and polymethylbenzenes with nitrosyl chloride in trifluoroacetic acid, leading to the products from chlorination and dehydrooligomerization of the aromatic substrates, were also studied.