2100-25-6

Basic information

• Product Name: 2,3,5,6-Tetramethyliodobenzene
• Synonyms: 2,3,5,6-TETRAMETHYLIODOBENZENE;3-IODODURENE;3-IODO-1,2,4,5-TETRAMETHYLBENZENE;1-iodo-2,3,5,6-tetramethylbenzene;3-Iodo-1,2,4,5-tetramethylbenzene,Pract.;1,2,4,5-TETRAMETHYL-3-IODOBENZENE;2,3,5,6-Tetramethyl-1-iodobenzene;2,3,5,6-Tetramethyliodobenzene,98%
• CAS NO: 2100-25-6
• Molecular Formula: C₁₀H₁₃I
• Molecular Weight: 260.11
• EINECS: 218-266-3
• Mol File: 2100-25-6.mol
• Article Data: 27

Chemical Properties

• Melting Point: 78-82 °C
• Boiling Point: 290 °C
• Flash Point: 122.007 °C
• Appearance: white fine crystalline powder
• Density: 1.4360 (rough estimate)
• Vapor Pressure: 0.00915mmHg at 25°C
• Refractive Index: 1.5718 (estimate)
• Sensitive: Light Sensitive
• BRN: 1862299
• CAS DataBase Reference: 2,3,5,6-Tetramethyliodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-Tetramethyliodobenzene(2100-25-6)
• EPA Substance Registry System: 2,3,5,6-Tetramethyliodobenzene(2100-25-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 2100-25-6(Hazardous Substances Data)

Usage

Chemical Properties

white fine crystalline powder

Uses

3-Iodo-1,2,4,5-tetramethylbenzene is an iodinated aromatic with antiinfective and antineoplastic properties.

InChI:InChI=1/C10H13I/c1-6-5-7(2)9(4)10(11)8(6)3/h5H,1-4H3

Upstream product

• 95-93-2 1,2,4,5-tetramethylbenzene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 91-20-3 naphthalene 
• 26976-92-1 1,2,4,5-tetramethyl-3,6-dihydrobenzene 

Downstream Products

• 83859-34-1 1,2,4,5-Tetramethyl-3-p-tolylselanyl-benzene 
• 112520-86-2 Benzenesulfonyl-(2,3,5,6-tetramethyl-phenyl)-acetonitrile 
• 85599-25-3 (2,3,5,6-Tetramethyl-phenyl)-phosphonic acid diethyl ester 
• 32134-67-1 (2,3,5,6-tetramethylphenyl)-λ³-iodanediyl diacetate 
• 77925-27-0 1,2,4,5-Tetramethyl-3-phenylselanyl-benzene 
• 2762-20-1 1-chloro-2,3,5,6-tetramethylbenzene 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 3360-65-4 1-(trifluoromethyl)-2,3,5,6-tetramethylbenzene 
• 54672-06-9 C₂₀H₂₆O 
• 85299-12-3 Thiobenzoic acid S-(2,3,5,6-tetramethyl-phenyl) ester 
• 64936-49-8 2,3,5,6-tetramethylphenyl selenocyanate 
• 85599-23-1 Diphenyl 2,3,5,6-tetramethylbenzenephosphonate 
• 83859-36-3 3-(4-Chloro-phenylselanyl)-1,2,4,5-tetramethyl-benzene 
• 102248-78-2 3-(2,2,2-trifluoroethoxy)-1,2,4,5-tetramethylbenzene 

Relevant articles and documents

Rapid aerobic iodination of arenes mediated by hypervalent iodine in fluorinated solvents

Arenes are rapidly converted to the corresponding iodides by aerobic oxidative iodination at room temperature by treatment with iodine and catalytic quantities of nitrous acid in a fluorinated solvent. Dichloroiodic acid is proposed as the actual iodination reagent.

A Mild and Convenient Procedure for Conversion of Aromatic Compounds into Their Iodides Using Ammonium Hexanitratocerate(IV)

Polymethylbenzenes, polymethoxybenzenes, and naphthalene are iodinated with tetrabutylammonium iodide, alkali metal iodides, or molecular iodine in the presence of ammonium hexanitrocerate(IV).Ammonium hexanitrocerate(IV) behaves as a catalyst in the latter system, whereas it is a reagent in the former two.

Regioselective iodination of activated arenes using phenyl trimethylammonium dichloroiodate in ionic liquid under microwave irradiation

The regioselective iodination of activated arenes has been achieved in the presence of phenyltrimethylammonium dichloroiodate and ionic liquid. The reaction has been carried out by both conventional heating as well as by microwave irradiation. Copyright Taylor & Francis, Inc.

Potassium 4-iodylbenzenesulfonate: Preparation, structure, and application as a reagent for oxidative iodination of arenes

A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60°C for 2 h, followed by filtration of the precipitate. A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by oxidation of 4-iodobenzenesulfonic acid with Oxone in water. This new reagent promises many practical applications as a thermally stable, water-soluble and recyclable hypervalent iodine oxidant, particularly useful for oxidative iodination of aromatic substrates.