28712-49-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5-iodothiophene is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique properties allow for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Chloro-5-iodothiophene serves as a crucial component in the production of agrochemicals. It contributes to the creation of effective pesticides and other agricultural products to enhance crop protection and yield.
Used in Materials Science for Electronic and Optoelectronic Applications:
2-Chloro-5-iodothiophene is utilized in the development of materials for electronic and optoelectronic applications. Its distinctive characteristics make it suitable for creating advanced materials used in electronic devices and optoelectronic systems.

Upstream product

• 96-43-5 2-thienyl chloride 
• 3437-95-4 2-Iodothiophene 
• 188290-36-0 thiophene 

Downstream Products

• 96-43-5 2-thienyl chloride 
• 73882-43-6 2-chloro-5-methoxythiophene 
• 81223-47-4 2-(5-chloro-2-thienylthio)-4-fluorobenzyl alcohol 
• 81223-45-2 2-(5-chloro-2-thienylthio)-4-fluorobenzoic acid 
• 1159524-75-0 C₁₁H₆Cl₂N₂O₃S 

Relevant academic research and scientific papers

METALLOENZYME INHIBITOR COMPOUNDS

The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

(Chiral) lithium-(magnesium-)zinc and lithium-cobalt combinations as dual reagents for aromatic deproto-metalation and aryl transfer to aldehydes

The deprotonating ability of mixed lithium-zinc or lithium-magnesium-zinc combinations containing amido and alkyl ligands in tetrahydrofuran were compared using anisole as substrate and iodine to quantitatively trap the formed arylmetal species. The results showed that the deprotonating ability is hampered if a Grignard reagent is employed to introduce the alkyl ligand, and is reduced when 2,2,6,6-tetramethylpiperidino ligands are replaced by less hindered/basic chiral amido or alkyls. Concerning the interception of the generated lithium-zinc aryl species by aldehydes, the presence of amido ligands leads to side reactions/lower yields, and no clear improvement was observed if lithium-magnesium-zinc aryl species are used. Racemic mixtures to very low enantioselectivities were noted when chiral amido ligands were incorporated in the composition of the bases. Still with enantioselective aryl transfer to aldehyde as purpose, the deprotonating ability of mixed lithium-cobalt combinations containing amido and alkyl ligands were compared using anisole as substrate and anisaldehyde to trap the formed arylmetal species. As before, the deprotonating ability is reduced when 2,2,6,6-tetramethylpiperidino ligands are replaced by less hindered/basic alkyls or chiral amido. The trapping step using aldehydes being in this case more efficient, even in the presence of amido ligands, the alcohols were obtained in higher yields. With recourse to a lower interception temperature, and using only bis[(R)-1-phenylethyl]amino as ligands, 32 and 22% yield, and 69 and 65% ee were obtained using, respectively, anisaldehyde and 3,4,5-trimethoxybenzaldehyde to intercept the metalated anisole.

Deprotonation of thiophenes using lithium magnesates

Thiophene was regioselectively deprotonated at C2 on treatment with 1/3 equiv of Bu3MgLi in THF at room temperature. The lithium arylmagnesate formed was either trapped with electrophiles or cross-coupled in a 'one-pot' procedure with aryl halides under palladium catalysis. 2-Chlorothiophene and 2-methoxythiophene were similarly deprotonated at C5 under the same reaction conditions. The enhancement of the reactivity of the base using TMEDA was evidenced using 1H NMR spectroscopy.

Reevaluation of benzyltrimethylammonium dichloroiodide, previously reported to be a selective iodinating agent

Benzyltrimethylammonium dichloroiodate, previously reported as an iodinating agent of thiophenes, appears to be a selective chlorinating agent of both thienyl and furyl derivatives containing a carbonyl group.

Bis-(trifluoroacetoxy)iodobenzene-iodine system: An efficient and selective reagent for iodination of thiophene derivatives

Bis-(trifluoroacetoxy)iodobenzene-iodine system is a good iodinating reagent of thiophene derivatives giving products with iodine atom in α-position on the thiophene ring.

Biphasic Electrophilic Halogenation of Activated Aromatics and Heteroaromatics with N-Halosuccinimides Catalyzed by Perchloric Acid

Catalytic amounts of 70percent perchloric acid (0.1 - 10, mostly 0.1 - 1, mol percent, based on substrate) initiate the regioselective halogenation of activated aromatics and heteroaromatics with N-halosuccinimide (NXS, X = Cl or Br) in two-phase solid-liquid systems (NXS/hexane or NXS/CCl4) at room temperature to give ring-halogenated products in high yields.For example, thiophene is transformed to 2-halo or 2,5-dihalo derivatives (yield 82-98percent) using 1 or 2 equiv of NXS, respectively.Unsymmetrical 2,5-dihalothiophenes are obtained in 70-82percent yield by reacting 2-halothiophenes with an appropriate NXS.The reaction of 3-bromothiophene with NBS affords 2,3-dibromothiophene in 93-99percent yield. 1,3-Dimethoxybenzene and 2,3-dimethylanisole are halogenated regiospecifically at the 4-position to give the corresponding products in 81-94percent yield.

Kinetics of Iodination of Thiophene and 2-Halothiophenes

The effect of substituents (Cl, Br and I) at the 2-position upon the rate of iodination with iodine monochloride in hydrochloric acid of thiophene at the 5-position, in 50percent aqueous acetic acid, had been studied at different temperatures.The rates and activation parameters for the 2-iodothiophene indicate an inductomeric mode of electron release by the iodine atom.