28712-49-4

Basic information

• Product Name: 2-Chloro-5-iodothiophene
• Synonyms: 2-Chloro-5-iodothiophene
• CAS NO: 28712-49-4
• Molecular Formula: C₄H₂ClIS
• Molecular Weight: 244.48115
• Mol File: 28712-49-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-Chloro-5-iodothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-5-iodothiophene(28712-49-4)
• EPA Substance Registry System: 2-Chloro-5-iodothiophene(28712-49-4)

Safety Data

• Hazardous Substances Data: 28712-49-4(Hazardous Substances Data)

Usage

General Description

2-Chloro-5-iodothiophene is a chemical compound with the molecular formula C4H2ClIS. It is a heterocyclic organic compound with a thiophene ring that has chlorine and iodine atoms attached to it. 2-Chloro-5-iodothiophene is used in various organic synthesis processes, such as in the production of pharmaceuticals and agrochemicals. It is also used in the development of materials for electronic and optoelectronic applications, due to its unique properties. 2-Chloro-5-iodothiophene is a valuable building block for the synthesis of complex organic molecules and is an important chemical intermediate in the manufacturing of various products in the pharmaceutical, agricultural, and materials science industries.

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 articles and documents

(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.

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.