56961-05-8

Usage

Usage

Intermediate in the production of dyes, pigments, and pharmaceuticals

Physical state

Colorless to light yellow liquid at room temperature

Odor

Strong amine-like odor

Toxicity

Toxic

Health hazards

Skin and eye irritation, respiratory and digestive tract irritation upon inhalation or ingestion

Flammability

Flammable

Additional hazards

May release toxic fumes when heated

Safety precautions

Proper handling and storage necessary to prevent exposure and potential harm to human health and the environment

Upstream product

• 915144-99-9 4-bromo-2,6-dichloro-N,N-dimethylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 634-93-5 2,4,6-trichloroaniline 
• 62-53-3 aniline 
• 91573-20-5 N,N-diacetyl-2,6-dichloroaniline 
• 62715-81-5 2,4,6-trichloro-diacetanilide 
• 77-78-1 dimethyl sulfate 
• 608-31-1 2,6-Dichloroaniline 
• 35122-82-8 N,N-Dimethyl-2,4,6-trichloroaniline 

Downstream Products

• 72228-74-1 3,5-dichloro-4-(dimethylamino)benzoic acid 
• 915144-99-9 4-bromo-2,6-dichloro-N,N-dimethylaniline 

Relevant academic research and scientific papers

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Chemistry of polyhalogenated nitrobutadienes, part 11: Ipso-formylation of 2-chlorothiophenes under Vilsmeier-Haack conditions

The regioselective ipso-formylation of electron-rich, 3,4-push-pull- substituted 2-chlorothiophenes under Vilsmeier-Haack conditions was performed in good yields. The synthetic scope of this new reaction was explored using various halothiophenes, chloroanilines, and 1-methyl-3-chloroindole. In comparison with their structural C-H analogs the chlorinated thiophenes, anilines, and the indole proved to be less reactive toward electrophilic attack by chloromethyleniminium salts.

Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines

A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.