16494-36-3

Basic information

• Product Name: 2-IODO-5-METHYLTHIOPHENE
• Synonyms: 2-IODO-5-METHYLTHIOPHENE;2-Methyl-5-iodothiophene;2-IODO-5-METHYLTHIOP;Thiophene, 2-iodo-5-Methyl-;2-Iodo-5-methylthiophene 97%
• CAS NO: 16494-36-3
• Molecular Formula: C₅H₅IS
• Molecular Weight: 224.06
• Product Categories: Thiophene&Benzothiophene;Thiophens;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks;Heterocycle-oher series
• Mol File: 16494-36-3.mol

Chemical Properties

• Boiling Point: 81-83°C 10mm
• Flash Point: 193°C
• Appearance: Yellow to dark red-orange/Liquid
• Density: 1.852 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.458mmHg at 25°C
• Refractive Index: n20/D 1.626(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-IODO-5-METHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODO-5-METHYLTHIOPHENE(16494-36-3)
• EPA Substance Registry System: 2-IODO-5-METHYLTHIOPHENE(16494-36-3)

Safety Data

• Statements: 22
• Safety Statements: 36/37/38
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16494-36-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Iodo-5-methylthiophene is used as a key intermediate in the synthesis of various organic compounds, particularly those involving thiophene rings. Its unique structure allows it to be a valuable building block for the creation of complex molecules with specific properties and functions.
2-Iodo-5-methylthiophene is used as a precursor for the preparation of:
Methylbis[2-(5-methyl)thienyl]boranedimethyl-terthienyl: 2-Iodo-5-methylthiophene is synthesized using 2-Iodo-5-methylthiophene as a starting material, and it may have potential applications in the development of new materials with unique electronic, optical, or magnetic properties.
5,5′-Dimethyl-2,2′-bithienyl: Another compound that can be prepared using 2-Iodo-5-methylthiophene, this molecule may find use in the design of novel organic materials, such as conducting polymers or organic semiconductors, which are important in the fields of electronics and optoelectronics.
Used in Pharmaceutical Industry:
2-Iodo-5-methylthiophene may also be utilized in the pharmaceutical industry as a starting material for the synthesis of new drugs or drug candidates. Its unique chemical structure could be exploited to develop molecules with specific biological activities, potentially leading to the discovery of new therapeutic agents.
Used in Material Science:
In the field of material science, 2-Iodo-5-methylthiophene could be employed in the development of novel materials with tailored properties. Its incorporation into polymers or other materials could result in new materials with improved electrical conductivity, optical properties, or other desirable characteristics.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 2427, 1969 DOI: 10.1017/S0009838800024678

InChI:InChI=1/C5H5IS/c1-4-2-3-5(6)7-4/h2-3H,1H3

Upstream product

• 554-14-3 2-Methylthiophene 
• 86134-27-2 trimethyl(5-methylthiophen-2-yl)stannane 
• 86134-26-1 2,5-bis-trimethylstannanyl-thiophene 
• 74-88-4 methyl iodide 
• 7553-56-2 iodine 
• 71-43-2 benzene 
• 123-76-2 levulinic acid 
• 1190072-80-0 bis(5-methyl-2-thienyl)iodonium trifluoroacetate 

Downstream Products

• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 16303-58-5 5,5'-dimethyl-2,2'-dithiophene 
• 125718-68-5 (Z)-2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-acrylic acid benzyl ester 
• 81294-10-2 2-ethynyl-5-methylthiophene 
• 72835-25-7 2-cyano-5-methylthiophene 
• 141858-79-9 (E)-1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)ethene 
• 125718-77-6 2-tert-Butoxycarbonylamino-3-(5-methyl-thiophen-2-yl)-propionic acid benzyl ester 
• 129770-69-0 5-(pyridin-4-yl) thiophene-2-carbaldehyde 
• 129770-73-6 N-<5-(4-pyridyl)-2-thenylidene>aniline 
• 106595-12-4 4-[2-bromo-3-ξ-(5-cyano-[2]thienyl)-allylidenamino]-benzoic acid 
• 13679-70-4 5-methylthiophene-2-carboxaldehyde 
• 19432-69-0 methyl 5-methylthiophene-2-carboxylate 
• 56921-01-8 5-methyl-4-nitro-thiophene-2-carboxylic acid methyl ester 
• 353269-67-7 2-Benzylidenmethyl-3-nitro-5-thiophen-carbonsaeure 

Relevant articles and documents

Highly tin-selective stille coupling: Synthesis of a polymer containing a stannole in the main chain

The incorporation of heavier Group 14 element heteroles into semiconducting polymers leads to unusual optoelectronic properties. However, polymers containing stannoles have not been accessible to date. We report a synthetic route to a well-defined, stannole-containing polymer, the first example of this class of π-conjugated polymers. This route was made possible by developing difunctionalized stannole monomers and highly tin-selective Stille coupling reactions that leave the tin in the stannole untouched. Compared to poly(3-n-hexylthiophene), the resulting polymer displays a remarkable bathochromic shift in its absorption. The budding potential of stannoles: A stannole monomer is prepared and employed in a highly tin-selective Stille coupling, giving a well-defined and non-annulated stannole-containing polymer, the first example from this class of π-conjugated polymers. Compared to polythiophenes, a strong bathochromic shift in the absorption spectrum was observed.

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.

Synthesis of thiophene/phenylene co-oligomers. III [1]. Thienyl-capped oligophenylenes

The author reports the synthesis of thienyl-capped oligophenylenes via improved synthetic schemes. These schemes are based on either the Grignard or Suzuki coupling reaction and enable the author to obtain the target compounds at appreciably high yields. Regarding several of these compounds, their synthesis and characterization are believed to be reported for the first time. The resulting materials have been fully characterized through the nmr and ir spectroscopy. The ir analysis is particularly useful in characterizing the materials of higher molecular weight, since those materials are difficult to dissolve in organic solvents.

Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

N-Arylation of various 2-acylated anilines with different electron-rich heteroaryl iodides (2- A nd 3-iodothiophenes, 2- A nd 3-iodobenzothiophenes?-, 2-iodobenzofuran) was achieved by using activated copper and potassium carbonate in dibutyl ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl or C3-free (benzo)furyl derivatives?-, affording original tri- A nd tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.

Photo-oxidative Cross-Dehydrogenative Coupling-Type Reaction of Thiophenes with α-Position of Carbonyls Using a Catalytic Amount of Molecular Iodine

A metal-free photo-oxidative intermolecular C-H/C-H coupling reaction of thiophenes is demonstrated with carbonyls using a catalytic amount of molecular iodine. In this system, molecular oxygen in the air acted as a terminal oxidant to regenerate molecular iodine. A mechanistic study was also performed.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)

The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.

Cascade iodination-fluorination synthesis of 2-fluorothiophene and 5-fluoro-2-thienyliodonium salts

The first synthesis of fluorine-containing 2-thienyliodonium salts was accomplished using cascade iodination-fluorination. According to this methodology, thiophene is first converted to bis(2-thienyl)iodonium hexafluorophosphate using an electrophilic iodination reaction. Upon heating with potassium fluoride, this salt undergoes regioselective fluorination producing 2-fluorothiophene. 2-Fluorothiophene is then iodinated again to yield fluorothienyliodonium salts.

Copper-catalyzed arene C-H bond cross-coupling

A highly regioselective, one-pot sequential iodination-copper-catalyzed cross-coupling of arene C-H bonds has been developed affording an efficient method for biaryl synthesis.

Mechanism of the lithium-iodine exchange in an iodothiophene

Solutions of 2-lithio-5-methylthiophene (4) were characterized using DNMR techniques and shown to be a mixture of monomer and dimer in THF-Et2O (3:2). The hypervalent iodine ate complex 5 (Ar2I-Li +), a presumed intermediate in the Li-I exchange with 2-iodo-5-methylthiophene, was observed by 13C and 7Li NMR spectroscopy at low temperatures (-130°C). At higher temperatures, the ate complex coalesced with 2-lithio-5-methylthiophene. A kinetic scheme was developed, which accounts for the exchange of the monomer 4M, dimer 4D, and 2-iodo-5-methylthiophene (6) with the ate complex 5. The rates of the various exchanges were obtained through a DNMR analysis of the variable temperature 13C and 7Li NMR spectra, and the thermodynamic and activation parameters were calculated. The monomer 4M and the ate complex 5 have similar reactivity as aryl donors in the Li-I exchange reaction, but 4M is at least 1000 times as reactive as the dimer 4D towards the iodide.