110-02-1 Usage
Uses
Used in Pharmaceutical Industry:
Thiophene is used as an important intermediate for the synthesis of various pharmaceuticals, including thiophene acetic pyridine and pyrantel. It is also used for the synthesis of new broad-spectrum cephalosporin antibiotics, making it a crucial component in the development of life-saving medications.
Used in Dye Industry:
Thiophene serves as a key building block in the synthesis of dyes, contributing to the creation of vibrant colors and hues in various applications.
Used in Resin Industry:
As a precursor for the production of resins, thiophene plays a vital role in the manufacturing of materials with diverse properties, such as Bakelite and other synthetic resins.
Used in Agrochemicals:
Thiophene is involved in the synthesis of agrochemicals, including sulfonylurea derivatives, which are new herbicides with ultra-efficient and low toxicity properties.
Used in Chemical Industry:
Thiophene is utilized as a solvent, similar to benzene, but suitable for a broader temperature range. It is also used in the manufacture of resins from thiophene-phenol mixtures and formaldehyde, as well as in organic syntheses.
Used in Chromatography Analysis:
Thiophene acts as a standard reference agent for chromatography analysis, ensuring accurate and reliable results in various chemical and biological studies.
Used in Organic Synthesis:
Thiophene is employed as a building block of various organic molecules and pharmaceuticals, providing functional properties and contributing to the development of innovative compounds.
Used in Manufacturing Color Films and Trick Photography:
Thiophene is utilized in the production of color films and trick photography, enhancing visual effects and expanding creative possibilities in the film industry.
Used in Extraction and Separation of Metals:
Thiophene serves as a complex reagent for the extraction and separation of uranium and other metals, playing a crucial role in the mining and metallurgical industries.
Heterocyclic compound
Thiophene is five-member heterocyclic compounds containing a sulfur atom and is presented at coal tar crude benzene at small amounts. It is a kind of colorless liquid having similar order as benzene aromatic with the boiling point being 84 °C. It is insoluble in water, and can be mixed with ethanol, ethyl ether, acetone, benzene, carbon tetrachloride, heptane, pyridine, and 1,4-dioxane. It is flammable, and has a high heat resistance without being decomposed when being heated to 850 °C. It is not polymerized under acidic conditions, nor does it be decomposed and be susceptible to oxidation. It also has moderate toxicity. The 5 atoms in thiophene ring belong to sp2 hybrid and located in the same plane. The occupied p-orbital of a pair of non-sharing electrons in the sulfur atom is parallel and overlapped with that of occupies the 4 carbon atoms which form 5 atoms/6 electrons closing conjugated system and thus having aromaticity. Thiophene is more prone to have electrophilic substitution reaction than benzene with electrophilic substitution mainly occurring in α-position (2-position or 5-position). An important derivative of thiophene is biotin which can have sulfonation reaction with concentrated sulfuric acid at room temperature with producing 2-thiophene acid which can be dissolved in sulfuric acid. Thereby, people often use this method to remove the thiophene in the crude benzene.
Thiophene can be used in the production of various kinds of dyes, perfumes, thermal shock resistant plastic, highly active solvent, stimulating hormone, insecticide, brightening agents, cosmetics and bio-activating substances and vitamins, anesthetics and antibiotics. It can also be used as the raw materials of preparing a broad spectrum anthelmintic pyrantel as well as antibacterial drugs cephalosporin I and II. Moreover, it can be used for further preparation of solvents such as sulfolane. Using chemical or electrochemical method can enable the synthesis of polythiophene, and having a conductivity of 2~10.6 × 103S/m after doping, and thus is a kind of conductive polymer materials of potential application.
Benzol Refining Products
Although thiophene is able to be chemically synthesized, the cost is too high. Thiophene is presented inside both shale oil and coal tar. The waste acid of crude benzol fraction resulted from the coal tar washed by concentrated sulfuric acid can be used as raw materials. It first undergoes hydrolysis in 110~150 °C, and then separated and purified to obtain thiophene. Thiophene is mainly presented in light benzene purified from the pre-rectification of crude benzene. When the light benzene was refined by adding hydrogen, thiophene is destroyed. When using light benzene acid for refining it, most of thiophene is polymerized with unsaturated compounds into tar-like substance with only a small amount of thiophene taking reaction with sulfuric acid for generating thiophene sulfonic acid which is easily extracted, thus greatly reducing the yield of thiophene.
When using light benzene acid for refining, thiophene is reacted together with sulfuric acid to generate thiophene-sulfonic acid which is dissolved in wasting sulfuric acid, clarify the sulfuric acid, remove the tarry substance, followed by hydrolysis distillation. The distilled condensed stuff was cooled and separated to obtain the thiophene-containing and benzenoid hydrocarbons-containing distilled crude oil. The crude distilled oil was neutralized by adding alkaline to be neutral or slightly basic with a distillation column (with theoretical plate number of 30 to 40) for distillation to obtain thiophene product (with thiophene content higher than 90%). During the rectification process, separate out the middle distilled fraction and reflux it back into the crude oil distillate. After distilling all the amount of thiophene, people can also distill out product of inter-xylene product (with content being higher than 95%) from the waste residue.
For this method of extraction of thiophene from waste sulfuric acid, thiophene extraction efficiency from crude benzene is low and demanding using hydrolysis distillation equipment with corrosion resistant materials. In order to increase the extraction efficiency of thiophene, many countries are studying new ways of thiophene extraction method from crude benzene, from which the relative successful method is extraction & rectification extraction method for thiophene (ER method). The approach is adding a suitable extraction agent to thiophene containing benzene in order to increase the relative volatility between benzene and thiophene in order to separate out the thiophene from rectification. In many kinds of extracting agents, α-pyrrolidone and N-methylpyrrolidone (NMP) have a strong dissolving ability to although this extraction agent is only with moderate selectivity. However, it has good chemical property and thermal stability, and is easy for recycling. The price is relatively cheap. All the above points make it be an appropriate extraction agent.
The above information is edited by the lookchem of Dai Xiongfeng.
Production methods
Thiophene is presented in the shale oil and coal tar. First use the waste acid of crude benzene washing as the raw material for hydrolysis at 110-150 °C. The gas coming from hydrolysis is put into the overhead condenser through hydrolysis distillation column. The condensed product has content of 15%-25% thiophene, 50%-60% xylene, and also benzene, toluene, methyl thiophene and some unknown substances. Per ton of waste acid can be extracted out for about 10 kg distillation product. After dehydration with solid sodium hydroxide and further refined purification by distillation, you can get thiophene product of 90%-95%. Chemical synthesis of thiophene can use butane and sulfur as raw materials; butane first undergoes dehydrogenation and then form a ring with sulfur to form thiophene. Laboratory prepare thiophene through the reaction between 1,4-dicarbonyl compound and phosphorus trisulfide.
Production Methods
Thiophene is present in coal tar and is recovered in the benzene distillation fraction (up to about 0.5% of the benzene present). Its removal from benzene is accomplished by mixing with concentrated sulfuric acid, soluble thiophene sulfonic acid being formed. Thiophene gives a characteristic blue coloration with isatin in concentrated sulfuric acid. The basic nomenclature of the thiophene ring system and its derivatives is indicated by the following: the sulfur atom is number 1, positions 2 and 5 are equivalent in the parent ring, as are the 3 and 4 positions.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Thiophene reacts violently with strong oxidizing agents and concentrated nitric acid causing fire and explosion hazards [Handling Chemicals Safely 1980. p. 899]. A mixture of Thiophene and N-nitrosoacetanilide exploded at 0°C [Ber., 1887, 30, 367].
Hazard
Flammable, dangerous fire risk.
Health Hazard
May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Safety Profile
Poison by ingestion and
intraperitoneal routes. Mildly toxic by
inhalation and subcutaneous routes. A very
dangerous fire hazard when exposed to heat
or flame. Explosive reaction with N-nitrosoacetanilide.
Violent or explosive
reaction with nitric acid. Incompatible with
oxidizing materials. To fight fire, use foam,
CO2, dry chemical. When heated to
decomposition it emits highly toxic fumes of
SOx.
Environmental fate
Photolytic. A rate constant 9.70 x 10-12 cm3/molecule?sec was reported for the reaction of
thiophene and OH radicals in the atmosphere at room temperature (Atkinson, 1985). Thiophene
also reacts with NO3 radicals in the atmosphere at rate constants ranging from 3.2 x 10-14
(Atkinson et al., 1985) to 3.93 x 10-14 cm3/molecule?sec (Atkinson, 1991).
Purification Methods
The simplest purification procedure is to dry thiophen with solid KOH, or reflux it with sodium, and fractionally distil it through a glass-helices-packed column. More extensive treatments include an initial wash with aqueous HCl, then water, drying with CaSO4 or KOH, and passage through columns of activated silica gel or alumina. Fawcett and Rasmussen [J Am Chem Soc 67 1705 1945] washed thiophene successively with 7M HCl, 4M NaOH, and distilled water, dried with CaCl2 and fractionally distilled it. *Benzene was removed by fractional crystallisation by partial freezing, and the thiophene was degassed and sealed in Pyrex flasks. [Also a method is described for recovering the thiophene from the *benzene-enriched portion.] [Beilstein 17 H 29, 17 I 17, 17 II 35, 17 III/IV 234, 17/1 V 297.]
Check Digit Verification of cas no
The CAS Registry Mumber 110-02-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 110-02:
(5*1)+(4*1)+(3*0)+(2*0)+(1*2)=11
11 % 10 = 1
So 110-02-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H4S/c1-2-4-5-3-1/h1-4H
110-02-1Relevant articles and documents
An Electron Spin Resonance Study of the Radical Cations of Pyrroles, Furans, and Thiophenes in Liquid Solution
Davies, Alwyn G.,Julia, Luis,Yazdi, Safieh N.
, p. 239 - 244 (2007/10/02)
Photolysis of alkylpyrroles in trifluoroacetic acid containing mercury(II) trifluoroacetate, alkylfurans in trifluoroacetic acid, or alkylthiophenes in sulphuric acid, induces oxidation to the corresponding radical cations.The e.s.r. spectra show that the electronic configuration is similar in all three species, the unpaired electron occupying the φA MO in which the heteroatom lies in a nodal plane.Photolysis of 2,6-dimethyl- and 2,6-diethyl-thiophene in trifluoroacetic acid containing mercury(II) trifluoroacetate, on the other hand, gave rise to spectra with a high g value (2.0062), showing hyperfine coupling to two non-equivalent pairs of alkyl groups in an unsymmetrical dimer.
ELECTRONIC EXCITATION OF ORGANOSULFUR RADICALS
Fabian, J.,Mayer, R.,Bleisch, S.,Zahradnik, R.
, p. 107 - 118 (2007/10/02)
Transition energies of neutral and ionic sulfur containing heterocyclic radicals have been calculated by the method of Longuet-Higgins and Pople and compared with experimental excitation energies obtained by UV/VIS absorption and photoelectron spectroscopy.In most cases the calculated transition energies satisfactorily match the ones found experimentally.A few compounds behave exceptionally.Discrepancies between the two sets of expermental values are attributed to different molecular geometries of the radical species.According to the calculations, the UV/VIS absorption spectra of recently synthesized sulfur and nitrogen containing radicals are compatible with the 1,2,3-dithiazolyl structure.
ESR Investigation of Radical Cations Formed from Aromatics and Heteroaromatics Adsorbed on Mo-Al2O3 Surfaces
Petrakis, L.,Meyer, P. L.,Jones, Gerald L.
, p. 1029 - 1038 (2007/10/02)
Molybdena-alumina is an important model catalyst system that has attracted considerable attention over the years.The behavior of adsorbed species on catalytic surfaces is also of interest because this may lead to a better understanding of the reaction mechanisms involved in the catalytic process.Using electron spin resonance, we have continued our systematic study of the molybdena-alumina system to which various aromatics and heteroaromatics have been added.We have investigated electron-transfer reactions with the molybdena-alumina surface and have also investigated the structural and dynamical aspects of the resulting adsorbed cations.Computer fitting of the cation ESR spectra has been carried out for a more precise determination of spectral parameters, and a comparison with solution spectral parameters has also been made.
