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
• Article Data: 26

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

2,4-Diiodoaniline is an aromatic hydrocarbon derivative and is used as an intermediate in pharmaceutical synthesis. It is used to synthesis of 5-Iodo-2-phenyl-benzimidazole.

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

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

Downstream Products

• 861613-82-3 N-(2-iodo-4-iodophenyl)acetamide 
• 89280-76-2 2-bromo-4,6-diiodoaniline 
• 626-00-6 1,3-Diiodobenzene 
• 2012-29-5 2,4-diiodophenol 
• 57279-79-5 (2,4-diiodo-phenyl)-hydrazine 

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+.

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.

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.