Thiophene compounds

Thiophenes compound is a five-membered heterocyclic compound containing only one sulfur atom with the basic structure being thiophene. Thiophene is presented in the shale oil and coal tar.

Thiophene is more active than benzene; it has photosensitivity with light shining causing carbon skeleton rearrangement; it can react with the metal; the sulfur in thiophene ring, under the action of the Ramey nickle, can be removed; substitution reaction can occur (mostly in the position 2); it can have ring open reaction upon being oxidized with different oxidizing agents being able to give different products; it can have nitration in the 2,5 position, generating nitro thiophene; it can be subject to halogenation, generating position 2 single halide, 2, 5-dihalide, 2, 3, 5-trihalides and tetrahalides; it can also have condensation reaction with benzene, generating benzothiophene.

Thiophene ring, due to that the unshared electron pair of the sulfur can form two carbon - carbon together into 6π electron system, with aromatic properties. Therefore, it can be subject to nitrification, sulfonation, halogenation and other electrophilic substitution reactions. The substituted positions include 2-position and 5-positions. It is much easier for thiophene to have electrophilic substitution reaction than benzene. E.g., thiophene, in the presence of mild condensation agent such as orthophosphoric acid can have Friedel-Crafts reaction with acyl group being introduced to the alpha- position.

In the presence of nitric acid, the thiophene can have reaction with iodide to generate 2-iodo-thiophene with a higher yield. Alternatively, you can also easily apply Mannich reaction to prepare 2-thienyl methylamine.
Friedel-Crafts

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 and other drugs. Thiophene, although may be chemically synthesized to make, but the cost is too high. Thiophene mainly exists in the light benzene obtained through pre-distillation of crude benzene. When the light benzene is subject to refinement through hydrogenation, the thiophene ring can be destroyed. When the light benzene undergoes pickling for refining, most of thiophene and unsaturated compounds can subject to polymerization into tar-like substance with only a small amount of sulfuric acid reacting with thiophene to generate easily extractable thiophene sulfonic acid, which greatly reduces the yield of thiophene.

When the light benzene undergoes pickling and refining, sulfuric acid can react with thiophene to generate thiophene-sulfonic acid to be dissolved in sulfuric acid. The waste sulfuric acid is clarified; the tarry substance was removed, followed by hydrolysis distillation. The distillate, after undergoing condensed cooling and separation, can give crude distilled oil containing thiophene and aromatic hydrocarbons. The crude distilled oil, after neutralization with alkaline to neutral or slightly alkaline, was further distilled in a distillation column with a theoretical plate number of 30 to 40, giving the product with thiophene content being higher than 90%. Upon distillation, the middle fraction was separated and concentrated to flow back into the crude oil distillate. After the distillation of all the thiophene, from the distillation residue, we can also obtain inter-xylene product with a purity being around 95%.

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Structure Chemical Name CAS MF
benzo[b]thiophen-4-ol benzo[b]thiophen-4-ol 361-02-4 C15H7Cl9F2
METHYL THIOPHENE-3-ACETATE METHYL THIOPHENE-3-ACETATE 58414-52-1 C7H8O2S
2,5-Diethylthiophene 2,5-Diethylthiophene 5069-23-8 C8H12S
2-BROMO-1-[5-(2-PYRIDINYL)-2-THIENYL]-1-ETHANONE 2-BROMO-1-[5-(2-PYRIDINYL)-2-THIENYL]-1-ETHANONE 306935-06-8 C11H8BrNOS
METHYL 4-CYANO-5-(METHYLTHIO)THIOPHENE-2-CARBOXYLATE METHYL 4-CYANO-5-(METHYLTHIO)THIOPHENE-2-CARBOXYLATE 175202-48-9 C8H7NO2S2
3-Hydroxybenzothiophene 3-Hydroxybenzothiophene 520-72-9 C8H6OS
methyl 2-amino-5-tert-butylthiophene-3-carboxylate methyl 2-amino-5-tert-butylthiophene-3-carboxylate 216574-71-9 C10H15NO2S
4-Iododibenzothiophene 4-Iododibenzothiophene 132034-89-0 C12H7IS
Benzo[b]thiophene, 4-fluoro- (9CI) Benzo[b]thiophene, 4-fluoro- (9CI) 310466-38-7 C8H5FS
3-THIOPHENECARBOXAMIDE  98 3-THIOPHENECARBOXAMIDE 98 51460-47-0 C5H5NOS
ETHYL 3-AMINO-4-CYANO-5-(METHYLTHIO)THIOPHENE-2-CARBOXYLATE ETHYL 3-AMINO-4-CYANO-5-(METHYLTHIO)THIOPHENE-2-CARBOXYLATE 116170-90-2 C9H10N2O2S2
THIOPHENE-3-THIOAMIDE THIOPHENE-3-THIOAMIDE 24044-76-6 C5H5NS2
METHYL 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLATE METHYL 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLATE 21211-07-4 C10H7ClO2S
4-METHYLDIBENZOTHIOPHENE 4-METHYLDIBENZOTHIOPHENE 7372-88-5 C13H10S
4-METHYLBENZOTHIOPHENE 4-METHYLBENZOTHIOPHENE 14315-11-8 C9H8S
3-CHLORO-6-METHYLBENZO(B)THIOPHENE-2-CA& 3-CHLORO-6-METHYLBENZO(B)THIOPHENE-2-CA& 34576-96-0 C10H7ClO2S
3-THIOPHENECARBOXYLIC ACID HYDRAZIDE 3-THIOPHENECARBOXYLIC ACID HYDRAZIDE 39001-23-5 C5H6N2OS
1-BENZOTHIOPHENE-2-SULFONYL CHLORIDE 1-BENZOTHIOPHENE-2-SULFONYL CHLORIDE 90001-64-2 C8H5ClO2S2
3-Methoxythiophene-2-carboxylic acid 3-Methoxythiophene-2-carboxylic acid 60166-83-8 C6H6O3S
4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID 4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID 19156-54-8 C9H10O2S
2-METHYLSULFONYLTHIOPHENE 2-METHYLSULFONYLTHIOPHENE 38695-60-2 C5H6O2S2
METHYL 3-CHLORO-6-METHYLBENZO(B)THIOPHE& METHYL 3-CHLORO-6-METHYLBENZO(B)THIOPHE& 59812-34-9 C11H9ClO2S
3-THIENYLZINC IODIDE 3-THIENYLZINC IODIDE 172035-85-7 C4H3ISZn
THIANAPHTHENE-2-CARBOXAMIDE THIANAPHTHENE-2-CARBOXAMIDE 6314-42-7 C9H7NOS
N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE 53370-51-7 C5H6N2OS
3-PHENOXYTHIOPHENE 3-PHENOXYTHIOPHENE 63285-84-7 C10H8OS
3-ACETYL-2-METHYL-5-PHENYLTHIOPHENE 3-ACETYL-2-METHYL-5-PHENYLTHIOPHENE 40932-63-6 C13H12OS
2,5-DIMETHYLTHIOPHENE-3-CARBOXYLIC ACID 2,5-DIMETHYLTHIOPHENE-3-CARBOXYLIC ACID 26421-32-9 C7H8O2S
THIOPHENE-3-CARBOXALDOXIME THIOPHENE-3-CARBOXALDOXIME 42466-50-2 C5H5NOS
2,5-DIMETHYL-THIOPHENE-3-CARBALDEHYDE 2,5-DIMETHYL-THIOPHENE-3-CARBALDEHYDE 26421-44-3 C7H8OS
6-METHYLBENZOTHIOPHENE 6-METHYLBENZOTHIOPHENE 16587-47-6 C9H8S
3-CYCLOHEXYLTHIOPHENE 3-CYCLOHEXYLTHIOPHENE 120659-34-9 C10H14S
7-CHLORO-BENZO[B]THIOPHENE 7-CHLORO-BENZO[B]THIOPHENE 90407-14-0 C8H5ClS
5-Nitrobenzothiophene 5-Nitrobenzothiophene 4965-26-8 C8H5NO2S
2-Ethylaminothiophene 2-Ethylaminothiophene 203730-54-5 C6H9NS
thiophene-2,3-
dicarbonitrile thiophene-2,3- dicarbonitrile 18853-42-4 C6H2N2S
2-(CHLOROACETYL)THIOPHENE 2-(CHLOROACETYL)THIOPHENE 29683-77-0 C6H5ClOS
THIOPHENE-2-CARBOXYLIC ANHYDRIDE THIOPHENE-2-CARBOXYLIC ANHYDRIDE 25569-97-5 C10H6O3S2
METHYL-2-ISOTHIOCYANATOTHIOPHENE-3-CARBOXYLATE METHYL-2-ISOTHIOCYANATOTHIOPHENE-3-CARBOXYLATE 126637-07-8 C7H5NO2S2
METHYL 3-CHLORO-6-FLUOROBENZO(B)THIOPHE& METHYL 3-CHLORO-6-FLUOROBENZO(B)THIOPHE& 21211-20-1 C10H6ClFO2S
6-Methoxybenzo(b)thiophene 6-Methoxybenzo(b)thiophene 90560-10-4 C9H8OS
3-methylbenzothiophene 3-methylbenzothiophene C9H8S
2-Thiopheneacetaldehyde 2-Thiopheneacetaldehyde 15022-15-8 C6H6OS
THIOPHENE-2-SULFONYLACETONITRILE THIOPHENE-2-SULFONYLACETONITRILE 175137-62-9 C6H5NO2S2
2-Thienylglyoxal 2-Thienylglyoxal 51445-63-7 C6H4O2S
Benzo[b]thiophene-3-ethylaMine Benzo[b]thiophene-3-ethylaMine 14585-66-1 C10H11NS
3,4-Dihexylthiophene 3,4-Dihexylthiophene 122107-04-4 C16H28S
2-THIENYLLITHIUM 2-THIENYLLITHIUM 2786-07-4 C4H3LiS
2-METHYLDIBENZOTHIOPHENE 2-METHYLDIBENZOTHIOPHENE 20928-02-3 C13H10S
5-ISOXAZOL-3-YLTHIOPHENE-2-SULFONYL CHLORIDE 5-ISOXAZOL-3-YLTHIOPHENE-2-SULFONYL CHLORIDE 160233-27-2 C7H4ClNO3S2
METHYL 3 6-DICHLOROBENZO(B)THIOPHENE-2-& METHYL 3 6-DICHLOROBENZO(B)THIOPHENE-2-& 21211-18-7 C10H6Cl2O2S
4-BROMO-2-CHLOROTHIOPHENE 4-BROMO-2-CHLOROTHIOPHENE 32431-93-9 C4H2BrClS
2-(PHENYLTHIO)THIOPHENE 2-(PHENYLTHIO)THIOPHENE 16718-12-0 C10H8S2
4-Bromothiophene-2-carbonitrile 4-Bromothiophene-2-carbonitrile 18791-99-6 C5H2BrNS
3-nitrobenzothiophene 3-nitrobenzothiophene 17402-80-1 C8H5NO2S
BIS(2-THIENYL) KETOXIME BIS(2-THIENYL) KETOXIME 10558-44-8 C9H7NOS2
5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine 5,7-dichloro-2,3-dihydrothieno3,4-b1,4dioxine 225518-49-0 C6H4Cl2O2S
2-Thiophenecarboxylic acid, tetrahydro- 2-Thiophenecarboxylic acid, tetrahydro- 19418-11-2 C5H8O2S
Poly(3-octylthiophene-2,5-diyl) Poly(3-octylthiophene-2,5-diyl) 104934-51-2 C12H18R2S
2-Amino-5-isopropyl-thiophene-3-carboxylic acid ethyl ester ,97% 2-Amino-5-isopropyl-thiophene-3-carboxylic acid ethyl ester ,97% 65416-85-5 C10H15NO2S
benzo[b]thiophen-7-ol benzo[b]thiophen-7-ol 77898-35-2 C8H6OS
3-Isothiocyanatothiophene 3-Isothiocyanatothiophene 61528-50-5 C5H3NS2
Benzotrithiophene Benzotrithiophene 29150-63-8 C12H6S3
2,5-DICHLOROTHIOPHENE 2,5-DICHLOROTHIOPHENE 173777-89-4 C4H2Cl2S
2(5 H)-THIOPHENONE 2(5 H)-THIOPHENONE 3354-32-3 C4H4OS
3-(2,5-DIBROMOTHIEN-3-YL)PROPANOIC ACID 3-(2,5-DIBROMOTHIEN-3-YL)PROPANOIC ACID 13191-40-7 C7H6Br2O2S
2-Methoxythiophene 2-Methoxythiophene 130410-20-7 C5H6OS
3-BROMOBENZOTHIOPHENE-2-CARBOXALDEHYDE 3-BROMOBENZOTHIOPHENE-2-CARBOXALDEHYDE 10135-00-9 C9H5BrOS
2-FLUOROTHIOPHENE 2-FLUOROTHIOPHENE 400-13-5 C4H3FS
3-BENZYLTHIOPHENE 3-BENZYLTHIOPHENE 27921-48-8 C11H10S
2-Isobutylthiophene 2-Isobutylthiophene 32741-05-2 C8H12S
2-HEXANOYLTHIOPHENE 2-HEXANOYLTHIOPHENE 26447-67-6 C10H14OS
3,4-Dibromothiophene-2,5-dicarboxaldehyde 3,4-Dibromothiophene-2,5-dicarboxaldehyde 25373-20-0 C6H2Br2O2S
2-(2,2-Dimethylpropyl)thiophene 2-(2,2-Dimethylpropyl)thiophene 4891-29-6 C9H14S
dibenzo[b,d]thiophen-3-aMine dibenzo[b,d]thiophen-3-aMine 25288-76-0 C12H9NS
4-Iodobenzothiophene 4-Iodobenzothiophene C8H5IS
3-(METHYLTHIO)THIOPHENE 3-(METHYLTHIO)THIOPHENE 20731-74-2 C5H6S2
2-IODO-BENZO[B]THIOPHENE 2-IODO-BENZO[B]THIOPHENE 36748-89-7 C8H5IS
2-Bromothiophene-3-carbonitrile 2-Bromothiophene-3-carbonitrile 56182-43-5 C5H2BrNS
2-Bromo-3-chlorothiophene 2-Bromo-3-chlorothiophene 77893-68-6 C4H2BrClS
Thiophene-3,4-diol Thiophene-3,4-diol 14282-59-8 C4H4O2S
2,3-DICHLOROTHIOPHENE 2,3-DICHLOROTHIOPHENE 17249-29-5 C4H2Cl2S
2-BROMO-3-IODOTHIOPHENE 2-BROMO-3-IODOTHIOPHENE 24287-92-1 C4H2BrIS
2-(N-HEPTANOYL)THIOPHENE 2-(N-HEPTANOYL)THIOPHENE 30711-40-1 C11H16OS
3-Aminomethylbenzo[b]thiophene 3-Aminomethylbenzo[b]thiophene 40615-04-1 C9H9NS
3-BROMOBENZOTHIOPHENE-2-CARBOXYLIC ACID& 3-BROMOBENZOTHIOPHENE-2-CARBOXYLIC ACID& 29174-66-1 C9H5BrO2S
2-Chloro-5-bromothiophene 2-Chloro-5-bromothiophene C4H2BrClS
2-Cyanotetrahydrothiophene 2-Cyanotetrahydrothiophene 112212-94-9 C5H7NS
6-chlorobenzo[b]thiophene 6-chlorobenzo[b]thiophene 66490-20-8 C8H5ClS
BENZO[B]THIOPHENE-3-CARBONITRILE BENZO[B]THIOPHENE-3-CARBONITRILE 24434-84-2 C9H5NS
LITHIUM 2-THIENYLCYANOCUPRATE  0.25M LITHIUM 2-THIENYLCYANOCUPRATE 0.25M 112426-02-5 C5H3CuLiNS
3-Ethylthiophene 3-Ethylthiophene 52006-63-0 C6H8S
3,4-Dibutylthiophene
3,4-Dibutylthiophene 85932-61-2 C12H20S
2-Iodobenzothiophene 2-Iodobenzothiophene C8H5IS
DIBENZOTHIOPHENE-D8 DIBENZOTHIOPHENE-D8 33262-29-2 C12H8S
2-Methylthieno[2,3-d]thiazole 2-Methylthieno[2,3-d]thiazole 61612-02-0 C6H5NS2
Methyl-3-(2-thienyl)=propionate Methyl-3-(2-thienyl)=propionate 16862-05-8 C8H10O2S
3,4-BIS(CHLOROMETHYL)-2,5-DIMETHYLTHIOPHENE 3,4-BIS(CHLOROMETHYL)-2,5-DIMETHYLTHIOPHENE 5368-70-7 C8H10Cl2S
5-Fluoro-2-thiophenecarbaldehyde 5-Fluoro-2-thiophenecarbaldehyde 29669-49-6 C5H3FOS
POLY(THIOPHENE-2,5-DIYL), BR TERMINATED POLY(THIOPHENE-2,5-DIYL), BR TERMINATED 25233-34-5 C4H4S
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