626-44-8 Usage
Description
1,3,5-Triiodobenzene is an organic compound with the chemical formula C6H3I3. It is a halogenated derivative of benzene, where three of the hydrogen atoms are replaced by iodine atoms. 1,3,5-TRIIODOBENZENE is known for its unique chemical and physical properties, which make it suitable for various applications in different industries.
Uses
1. Used in Chemical Synthesis:
1,3,5-Triiodobenzene is used as a key building block in the synthesis of conjugated microporous polymers through cationic cyclization polymerization. These polymers have potential applications in gas storage, separation, and catalysis due to their porous structure and tunable chemical properties.
2. Used in Optical Materials:
1,3,5-Triiodobenzene is also utilized in the development of optical materials. Its unique electronic and optical properties make it a valuable component in the creation of materials with specific light absorption, emission, or transmission characteristics. These materials can be used in various applications, such as optical sensors, displays, and photovoltaic devices.
Synthesis
1,3,5-Triiodobenzene was synthesized by reacting 2,4,6-triiodoaniline with NaNO2 in the presence of copper(I) oxide.Experimental procedure: Finely ground NaNO2 (1.95 g,
0.028 mol) was slowly added with stirring to sulfuric acid
(3.5 mL). Then a solution of 2,4,6-triiodoaniline(2.90 g,
6.16 mmol) in glacial AcOH (130 mL) was added dropwise with
stirring and cooling at such a rate that the temperature of the
reaction mixture was kept below 20 °C. Following addition of
the amine, the reaction mixture was stirred at ≈20 °C for about
30 min. The resulting solution of the diazonium salt was added
dropwise to a suspension of copper(I) oxide (2.52 g) in dry ethanol (70 mL) with vigorous stirring over 15 min. The reaction
mixture was brought to boiling and stirred for 30 min until
elimination of nitrogen ceased. Then the mixture was cooled,
kept for one day, poured into ice water (300 mL), and extracted
with benzene (3×50 mL). The benzene extracts were dried with
anhydrous Na2SO4 and the solvent was distilled off in vacuo.
The residue was repeatedly recrystallized from benzene. The
yield was 2.01 g (84%), m.p. 182 °C (cf. lit. data11: m.p. 183 °C).
1H NMR (CDCl3), δ: 8.02 (s, 3 H, CH). 13C NMR (CDCl3),
δ: 79; 128.
Check Digit Verification of cas no
The CAS Registry Mumber 626-44-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 6 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 626-44:
(5*6)+(4*2)+(3*6)+(2*4)+(1*4)=68
68 % 10 = 8
So 626-44-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H3I3/c7-4-1-5(8)3-6(9)2-4/h1-3H
626-44-8Relevant articles and documents
Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions
Desaintjean, Alexandre,Danton, Fanny,Knochel, Paul
supporting information, p. 4461 - 4476 (2021/08/13)
A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents are prepared in toluene within 10 to 120 minutes between 78 C and 25 C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as triazene or nitro, are tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arene and alkene derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.
Size-controlled synthesis of conjugated polymer nanoparticles in confined nanoreactors
Deng, Sheng,Zhi, Jian,Zhang, Xianmei,Wu, Qingqing,Ding, Yun,Hu, Aiguo
supporting information, p. 14144 - 14148 (2015/02/19)
Soluble conjugated polymeric nanoparticles are synthesized by Suzuki-type polycondensation of two monomers (Ax + By, x>2, y≥2) in the channel of ordered mesoporous silica-supported carbon nano-membranes (nanoreactors). These synthesized soluble conjugated microporous polymers (SCMPs) exhibit uniform particle-size distributions and well-controlled particle sizes. The control of particle size stems from the fact that the polycondensations exclusively take place inside the mesochannels of the nano-reactors. Photo-luminescence studies show that polymeric nanoparticles with tetraphenylethene and pyrene substructures are highly fluorescent. The combination of both physical stability and process-ability offered by the soluble polymeric nanoparticles makes them particularly attractive in light emitting and other optoelectronic applications.
Facile aromatic finkelstein iodination (AFI) reaction in 1,3-dimethyl-2-imidazolidinone (DMI)
Yamashita, Ken-Ichi,Tsuboi, Michihiro,Asano, Motoko S.,Sugiura, Ken-Ichi
experimental part, p. 170 - 175 (2011/11/29)
In this communication, we report the superior role of 1,3-dimethyl-2- imidazolidinone (DMI) as a solvent for aromatic Finkelstein iodination (AFI), the conversion of aryl bromides to aryl iodides. DMI accelerates the reaction rate and affords product(s) that could not be prepared using previous methods. Our findings for AFI avoid the use of toxic solvents such as N,N-dimethylformamide and hexamethylphosphoramide. Taylor & Francis Group, LLC.