6324-50-1

Basic information

• Product Name: 2,4,6-Trichloroiodobenzene
• Synonyms: 1,3,5-TRICHLORO-2-IODOBENZENE;1-IODO-2,4,6-TRICHLOROBENZENE;2-Iodo-1,3,5-trichlorobenzene;2,4,6-Trichloro-1-iodobenzene;Benzene,1,3,5-trichloro-2-iodo-;BUTTPARK 50\07-79;2,4,6-TRICHLOROIODOBENZENE
• CAS NO: 6324-50-1
• Molecular Formula: C₆H₂Cl₃I
• Molecular Weight: 307.34
• Mol File: 6324-50-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 297.5°C at 760 mmHg
• Flash Point: 133.7°C
• Appearance: /
• Density: 2.085g/cm³
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: 1.651
• Sensitive: Light Sensitive
• BRN: 1868441
• CAS DataBase Reference: 2,4,6-Trichloroiodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trichloroiodobenzene(6324-50-1)
• EPA Substance Registry System: 2,4,6-Trichloroiodobenzene(6324-50-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 6324-50-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4,6-Trichloroiodobenzene is used as a reagent in organic synthesis for its high reactivity in cross-coupling reactions and nucleophilic substitution reactions. Its unique properties make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,4,6-Trichloroiodobenzene is used as an intermediate in the production of various drugs. Its reactivity and versatility contribute to the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Manufacturing:
2,4,6-Trichloroiodobenzene is utilized as an intermediate in the synthesis of agrochemicals, which are essential for crop protection and enhancement of agricultural productivity. Its role in this industry highlights its importance in developing effective and safe agrochemical products.
Used in Dye and Specialty Chemicals Production:
TCI is also employed in the manufacture of dyes and other specialty chemicals, where its unique chemical properties contribute to the creation of high-quality and specialized products for various applications.

InChI:InChI=1/C6H2Cl3I/c7-3-1-4(8)6(10)5(9)2-3/h1-2H

Upstream product

• 401631-89-8 C₁₀H₁₂Cl₃N₃ 
• 108-70-3 1,3,5-trichlorobenzene 
• 64-19-7 acetic acid 
• 634-93-5 2,4,6-trichloroaniline 
• 60-29-7 diethyl ether 
• 861530-02-1 1,3,5-trichloro-2-iodosyl-benzene 

Downstream Products

• 56558-17-9 2,3',4,4'6-pentachlorobiphenyl 
• 60145-21-3 2,2',4,5',6-pentachlorobiphenyl 
• 60233-25-2 2,2',3,4',6'-pentachlorobiphenyl 
• 50-43-1 2,4,6-trichlorobenzoic acid 
• 69807-93-8 4,4,5,5-tetramethyl-2-(2,4,6-trichlorophenyl)-1,3,2-dioxaborolane 
• 1290100-54-7 (E)-4-(2,4,6-trichlorophenyl)but-3-en-2-one 
• 157062-88-9 tris(2,4,6-trichlorophenyl)borane 
• 6575-05-9 2,4,6-Trichlorobenzonitrile 
• 32598-12-2 PCB 75 
• 60233-24-1 2,3',4,6-tetrachlorobiphenyl 
• 63980-00-7 ethyl-(2,4,6-trichloro-phenyl)-sulfide 
• 6284-83-9 1,3,5-trichloro-2,4-dinitrobenzene 
• 39485-83-1 2,2',4,4',6-pentachlorobiphenyl 
• 56558-18-0 2,3',4,5',6-pentachlorobiphenyl 

Relevant articles and documents

Late stage iodination of biologically active agents using a one-pot process from aryl amines

A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(ii) dichloride reduction and the use of the one-pot diazotisation-iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-d-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.

Synthesis of Isoxazolines and Isoxazoles Inspired by Fipronil

Phenylpyrazoles (or arylpyrazoles) are known to be extremely potent as noncompetitive inhibitors of the GABA-gated chloride channel on the GABA receptor. This project involves the synthesis of novel isoxazole and isoxazoline heterocycles that have similar

PYRAZOLECARBOXAMIDE DERIVATIVES AND THEIR USE AS MICROBIOCIDES

Compounds of Formula (I) wherein R1 is C1-C4alkyl or C1-C4 haloalkyl; R2 is C1-C4alkyl; R3 is hydrogen or halogen; R4 is hydrogen, C1-C4alkyl or C1-C4halogenalkyl; R5 is hydrogen, halogen, C1-C4alkyl or C1-C4halogenalkyl; R6 is hydrogen, halogen, C1-C4alkyl, C2-C6alkenyl or C3-C6alkinyl; R7 is hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C3-C6alkinyl, C3-C6cycloalkyl-C3-C6alkinyl, halophenoxy, halophenyi, C1-C6haloalkyl, C1-C6haloakoxy, C2-C6haloalkenyl, or C2-C6haloalkenyloxy; R8 is hydrogen, halogen, C1-C4alkyl, C2-C6alkenyl or C3-C6alkinyl; with the provisio that at least one of R6, R7 and R8 is different from hydrogen; n is 0 or 1, are suitable for use as microbriocides.

PYRAZOLECARBOXAMIDE DERIVATIVES AND THEIR USE AS MICROBIOCIDES

Compounds of Formula (I) wherein R1 is C1-C4alkyl or C1 -C4 haloalkyl; R2 is C1-C4alkyl; R3 is hydrogen or halogen; R4 is hydrogen, C1-C4alkyl or C1-C4halogenalkyl; R5 is hydrogen, halogen, C1-C4alkyl or C1-C4halogenalkyl; R6 is hydrogen, halogen, C1-C4alkyl, C2-C6alkenyl or C3-C6alkinyl; R7 is hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C3-C6alkinyl, C3-C6cycloalkyl- C3-C6alkinyl, halophenoxy, halophenyi, C1-C6haloalkyl,C1-C6haloakoxy, C2- C6haloalkenyl, or C2-C6haloalkenyloxy; R8 is hydrogen, halogen, C1-C4alkyl, C2-C6alkenyl or C3-C6alkinyl; with the provisio that at least one of R6, R7 and R8 is different from hydrogen; n is 0 or 1, are suitable for use as microbriocides.

Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates

The diazotization of aryl amines at room temperature in paste form with NaNO2, p-TsOH and a small amount of water, followed by treatment with KI provides a new, simple, and effective route for the preparation of various aryl iodides. The water-paste and strong acid-free reaction conditions are environmentally friendly and compatible with acid-sensitive functional groups.

Sulfonic acid based cation-exchange resin: A novel proton source for one-pot diazotization-iodination of aromatic amines in water

A convenient and simple one-pot method for the preparation of iodoarenes at room temperature has been developed, by sequential diazotization-iodination of aromatic amines with NaNO2/KI in the presence of a sulfonic acid based cation-exchange resin in water. This inexpensive, noncorrosive and eco-friendly synthetic route is general in nature and allows for the preparation of iodoarenes with an electron-donating or -withdrawing group in various positions from the corresponding amines in 50-98% yields. Georg Thieme Verlag Stuttgart.

A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines

We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield. Georg Thieme Verlag Stuttgart.

1-Aryl-3,3-dialkyltriazenes: A convenient synthesis from dry arenediazonium o-benzenedisulfonimides - A high yield break down to the starting dry salts and efficient conversions to aryl iodides, bromides and chlorides

This research comprises three parts. The first part regards the synthesis of 1-aryl-3,3-dialkyltriazenes 3 by reaction of dry arenediazonium o-benzenedisulfonimides 1, also coming from weakly basic aromatic amines with dimethylamine or diethylamine in aqueous solution at 0-5 °C. Yields were usually greater than 90% and there was the possibility of recovering the o-benzenedisulfonimide (5), which could be reused to prepare the salts 1. In the second part it was demonstrated that there is the possibility of reconverting the triazenes 3 into the starting stable dry salts 1 by using 5 as acid. The reactions were carried out in glacial acetic acid at 50-55 °C and normally afforded salts 1 in yields of around 90-99%. The third part concerns the setting up of two procedures for the conversion of 3 to aryl iodides 9, bromides 10 and chlorides 11. Procedure A used the corresponding aqueous hydrogen halides in acetonitrile at r.t. or 60 °C, sometimes in the presence of aqueous HBF4, sometimes Cu powder (25 examples, yields 65%-88%). Procedure B usually used anhydrous methanesulfonic acid and tetraalkylammonium halides in anhydrous acetonitrile at temperatures varying from r.t. to 80 °C, sometimes in the presence of Cu (16 examples, yields 65-88%).

Extensive halogen scrambling and buttressing effects encountered upon treatment of oligobromoarenes with bases

As a rule, tri-, tetra- and pentahaloarenes readily undergo ortho-lithiation when treated with amide-type bases. However, halogen migration occurs whenever the substrate contains three or more contiguous halogen atoms, provided that at least one of them is bromine or iodine. Dismutation and reduction processes often take place concomitantly. In this manner, a variety of organometallic intermediates may be formed, the driving force always being a decrease in basicity. When no such energy gain can be achieved, a sterically crowded substrate may just turn out to be inert; this was found to be the case with 1,5-dibromo-3-fluoro-2-(trimethylsilyl)benzene, 1,5-dibromo-3-fluoro-2,4-bis(trimethylsilyl)benzene, and 1,5-dibromo-3-fluoro-2,4-diiodobenzene. Buttressing effects are apparently strong enough to prevent expedient deprotonation of those substrates.

Nucleophilic Displacement in Polyhalogenoaromatic Compounds. Part 11. Kinetics of Protiodeiodination of Iodoarenes in Dimethyl Sulphoxide-Methanol

The rates of methoxide-ion induced protiodeiodination of a number of polychloroiodobenzenes and their derivatives have been measured in dimethyl sulphoxide-methanol (9:1 v/v; 323.2 K).The true reagent under these conditions appears to be the dimethyl sulphoxide anion, and the rates of reaction in some cases appear to approach that expected of a diffusion controlled process.This corresponds to a major decrease in the efficacy of further activating substituents in the aromatic system, altough deactivating groups such as p-OMe still show large effects.Chlorine promotes protiodeiodination in the order of efficiency o-Cl > m-Cl > p-Cl; the trifluoromethyl group activates displacement in the order o-CF3 > p-CF3 > m-CF3, although with much less difference between isomeric sites. o-Nitro-groups promote protiodeiodination whereas the p-nitro-group encourages methoxydeiodination.No evidence of methoxydeiodination was found in attack of the polychloroiodobenzenes, although the rates of methoxydechlorination of the corresponding polychlorobenzenes suggest that in some cases this might occur.Evidence rejecting the possible SRN1 mechanism and supporting nucleophilic attack by a carbanionic species upon iodine is presented.