533-70-0

Basic information

• Product Name: 2,4-Diiodoaniline
• Synonyms: 2,4-DIIODOANILINE;2,4-Diiodobenzene;(2,4-diiodophenyl)amine
• CAS NO: 533-70-0
• Molecular Formula: C₆H₅I₂N
• Molecular Weight: 344.92
• Mol File: 533-70-0.mol

Chemical Properties

• Melting Point: 94-95°C
• Boiling Point: 346 °C at 760 mmHg
• Flash Point: 163 °C
• Appearance: /
• Density: 2.7480
• Vapor Pressure: 5.94E-05mmHg at 25°C
• Refractive Index: 1.767
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.74±0.10(Predicted)
• CAS DataBase Reference: 2,4-Diiodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Diiodoaniline(533-70-0)
• EPA Substance Registry System: 2,4-Diiodoaniline(533-70-0)

Safety Data

• Hazardous Substances Data: 533-70-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Diiodoaniline is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs and medicinal compounds. Its unique chemical structure allows it to be a key component in the development of new pharmaceuticals with potential therapeutic benefits.
Used in the Synthesis of 5-Iodo-2-Phenyl-Benzimidazole:
Specifically, 2,4-Diiodoaniline is utilized in the production of 5-Iodo-2-Phenyl-Benzimidazole, a compound with potential applications in the medical field. The synthesis of this compound leverages the reactivity and properties of 2,4-Diiodoaniline, highlighting its importance in the development of novel pharmaceutical agents.

Synthesis

2,4-Diiodoaniline is generally prepared by the reactions of aniline with iodine in the presence of oxidants, with ICl vapor.Step: Freshly distilled aniline (1mL, 11mmol) was dissolved in concentrated HCl (50 mL) and diluted with water to 0.5 L. Then KICl2 (5.2 g, 22 mmol) was added portionwise with vigorous stirring at ≈20 °C, this being followed by the gradual formation of a grayish precipitate. After completion of the reaction (3h), the precipitate was filtered off and recrystallized from benzene with addition of activated carbon. The yield of diiodoaniline was 2.14g (57%), m.p. 95 °C.1H NMR (CDCl3), δ: 3.74 (br.s, 2 H, NH2); 6.49 (d, 1 H, C(6)H, J = 8.2 Hz); 7.36 (dd, 1 H, C(5)H, J1 = 1.0 Hz; J2 = 8.2 Hz); 7.87 (d, 1 H, C(3)H, J = 1 Hz).

InChI:InChI=1/C6H5I2N/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

Upstream product

• 7790-99-0 Iodine monochloride 
• 64-19-7 acetic acid 
• 62-53-3 aniline 
• 615-43-0 2-iodophenylamine 
• 116529-48-7 2,6-diiodo-3-nitro-aniline 
• 540-37-4 p-aminoiodobenzene 
• 7553-56-2 iodine 
• 7647-01-0 hydrogenchloride 
• 6303-60-2 2,4-diiodo-1-nitro-benzene 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 57279-79-5 (2,4-diiodo-phenyl)-hydrazine 
• 2012-29-5 2,4-diiodophenol 
• 626-00-6 1,3-Diiodobenzene 
• 89280-76-2 2-bromo-4,6-diiodoaniline 
• 68867-20-9 6-iodo-2-methyl-1,3-benzothiazole 

Relevant articles and documents

Salicylaldimine-functionalized poly(m-phenyleneethynylene) as turn-on chemosensor for ferric ion

A new turn on fluorescent probe for ferric ion based on poly(m-phenyleneethynylene salicylaldimine) (PPE-IM) has been developed. The preparation of PPE-IM involves post-polymerization functionalization of the corresponding polymeric amine, PPE-AM, via the condensation with salicylaldehyde. The degree of polymerization of both PPE-IM and PPE-IM is 17 with polydispersity index of 1.5. In aqueous solution, the polymeric PPE-IM is highly stable unlike its small molecule analog which is gradually hydrolyzed. The weak fluorescence of initial PPE-IM (λem = 470) is greatly enhanced by 300 folds upon the addition of Fe3+. The 1H NMR reveals that the fluorescence enhancement is caused by Fe3+-induced hydrolysis of the imine group. The sensing system shows a detection limit of 0.14 μM of Fe3+.

AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS

The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS

The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).

Iodination of industrially important aromatic compounds with aqueous potassium triiodide

A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.

Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions

1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.

Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of N-Iodosuccinimide

An iron(III)-catalyzed method for the rapid and highly regioselective iodination of arenes has been developed. Use of the powerful Lewis acid, iron(III) triflimide, generated in situ from iron(III) chloride and a readily available triflimide-based ionic liquid allowed activation of N-iodosuccinimide (NIS) and efficient iodination under mild conditions of a wide range of substrates including biologically active compounds and molecular imaging agents.

Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol

An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.

Ionic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes

Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.