6284-83-9

Usage

Uses

Used in Dye and Pigment Production:
1,3,5-trichloro-2,4-dinitrobenzene is utilized as a chemical intermediate for the production of dyes and pigments, contributing to the coloration and stability of these substances in different manufacturing processes.
Used in Pharmaceutical Synthesis:
1,3,5-trichloro-2,4-dinitrobenzene also serves as an intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of various organic compounds used in the medical industry.
Used in Organic Compound Synthesis:
1,3,5-trichloro-2,4-dinitrobenzene is employed in the synthesis of other organic compounds, highlighting its versatility in the realm of chemical production and research.

InChI:InChI=1/C6HCl3N2O4/c7-2-1-3(8)6(11(14)15)4(9)5(2)10(12)13/h1H

Upstream product

• 108-70-3 1,3,5-trichlorobenzene 
• 18708-70-8 2,4,6-trichloronitrobenzene 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 6324-50-1 1,3,5-trichloro-2-iodobenzene 

Downstream Products

• 858259-34-4 3-chloro-2,4-dinitro-1,5-dipiperidino-benzene 
• 50903-09-8 3,5-dichloro-2,4-dinitro-anisole 
• 18523-15-4 1,3,5-trimethoxy-2,4-dinitro-benzene 
• 860556-89-4 3-chloro-1,5-dimethoxy-2,4-dinitro-benzene 
• 244037-24-9 2,4,6-trichloro-3-nitroanisole 
• 861081-00-7 1-chloro-3,5-dimethoxy-2,4-dinitro-benzene 
• 129612-08-4 1,3,5-triethoxy-2,4-dinitro-benzene 
• 98137-93-0 1,3,5-Triazido-2,4-dinitro-benzol 
• 39994-58-6 2,4-dinitro-benzene-1,3,5-triyltriamine 
• 39994-56-4 5-chloro-4,6-dinitro-m-phenylenediamine 
• 860602-85-3 2,4-dinitro-1,3,5-triphenoxy-benzene 
• 56224-44-3 (3,5-Dichloro-2,6-dinitro-phenyl)-dipropyl-amine 
• 618-86-0 1-chloro-3,5-dinitrobenzene 
• 28073-03-2 1,2,3,5-tetrachloro-4,6-dinitrobenzene 

Relevant academic research and scientific papers

Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution

The phenylurea moiety is a ubiquitous synthon in supramolecular chemistry. Here we report that the introduction of chlorine or bromine atoms in the ortho positions to the urea unit is a simple and very efficient way to improve its intermolecular hydrogen bond (HB) donor character. This effect was demonstrated in solution both in the context of self-association of bis-ureas and hydrogen bonding of mono-ureas to strong HB acceptors. The Royal Society of Chemistry 2014.

A newly developed synthesis of 1,3,5-trichlorobenzene (sym. TCB) from aniline

1,3,5-Trichlorobenzene (sym. TCB) has been synthesised by diazotisation of 2,4,6-trichloroaniline (sym. TCA) (by converting aniline into anilinium chloride followed by its chlorination) in the presence of H2SO4/NaNO2 and H3PO2. The reaction parameters for the synthesis of both sym, TCA as well as sym. TCB have also been established in order to get better purity and higher yields, sym. TCA and sym. TCB have been characterized by elemental analysis, Fourier Transform Infra Red (FTIR) and NMR spectroscopy. Further, different reaction parameters for the nitration of sym. TCB to get 1,3,5- trichloro-2,4,6-trinitrobenzene (TCTNB) and its amination to get pure 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) have also been established. A comparison of properties of TATB obtained from imported sym. TCB and from laboratory prepared sym. TCB validates the product.

Electrophilic Aromatic Substitution. Part 33. Kinetics and Products of Aromatic Nitrations in Solutions of Dinitrogen Pentaoxide in Nitric Acid

The kinetics and/or products of reaction, in nitric acid containing 0-5 mol dm-3 of dinitrogen pentaoxide, of phenyltrimethylammonium perchlorate, 1,2-dichloro-4-nitrobenzene, 2,4-dinitrotoluene, 1,4-dichloro-2-nitrobenzene, 1,2,4-trichloro-5-nitrobenzene, 1,2,4,5-tetrachlorobenzene, pentachlorobenzene, 1,2,3-trichlorobenzene, 1,3,5-trichloro-2-nitrobenzene, 1,2-dichloro-3-nitrobenzene, 1,2,3,4-tetrachlorobenzene, and 1,3-dichloro-2-nitrobenzene, have been studied.For each substrate investigated kinetically, rate coefficients for nitration in solutions containing more than ca. 2 mol dm-3 dinitrogen pentaoxide increase more quickly than the concentration of nitronium ion.In the cases of 1,2,4,5-tetrachlorobenzene, 1,4-dichloro-2-nitrobenzene, and 1,2,4-trichloro-5-nitrobenzene, but not with the other substrates, there was evidence for the formation of, in addition to expected aromatic nitroproducts, unstable cyclohexadiene products.Those from 1,2,4-trichloro-5-nitrobenzene were identified as a diastereomeric pair of 3,5,6-trichloro-2,4-dinitrocyclohexa-2,5-dienyl nitrates.A mechanism for the formation of these products is proposed.

Electrophilic Aromatic Substitution. Part 32. The Nitration of 1,3,5-Trichloro-2-nitrobenzene, 1,3,5-Trichloro-2,6-dinitrobenzene, and 1,2,3,5-Tetrachloro-4,6-dinitrobenzene in Sulphuric Acid and in Oleum

The kinetics of nitration of 1,3,5-trichloro-2-nitrobenzene (TCNB) in sulphuric acid and in oleum at 25, 50, and 75 deg C, and of 1,3,5-trichloro-2,4-dinitrobenzene (TCDNB) in oleum at 150 deg C have been measured. 1,2,3,5-Tetrachloro-4,6-dinitrobenzene (TetCDNB) reacts with nitric acid in sulphuric acid and in oleum at 150 deg C; the rate profile for the reaction shows a nitration process to be occuring.From TCNB in sulphuric acid the yield of TCDNB was not quite quantitative and at 25 deg C in oleum a small amount of 1,2,3,5-tetrachloro-4-nitrobenzene was also formed.TCDNB gave a mixture of TCTNB (the major product) and TetCDNB in proportions which varied with acidity; lower acidities were more favourable to the formation of TetCDNB.The total amount of chlorine present in the TCDNB, TCTNB, and TetCDNB was equal to that present in the TCDNB at the start of the reaction.The nitration of TetCDNB in sulphuric acid at 150 deg C gave carbon dioxide and hydrogen chloride, and some sulphur dioxide and nitric oxide or nitrogen dioxide.In the nitration of TCDNB this compound produces the chlorinating agent and reacts with it to give TetCDNB.The chlorinating agent can chlorinate added 1,3-dinitrobenzene.The use of H(15)NO3 in the nitration TCDNB leads to (15)N-incorporation in it and in the TetCDNB produced.Separate nitration of TetCDNB causes only slight (15)N-incorporation into it.It is suggested that in addition to the main route of nitration leading to TCTNB, the nitration of TCDNB gives an ipso-Wheland intermediate by attack of nitronium ion at a nitrated position; this intermediate may either return to starting material or give a diene by nucleophilic capture.Decomposition of the diene gives hydrogen chloride or chloride anion which is oxidised by nitric acid to an electrophilic chlorinating agent.