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
3-Hexylthiophene 3-Hexylthiophene 1693-86-3 C10H16S
Methyl 3-amino-4-methylthiophene-2-carboxylate Methyl 3-amino-4-methylthiophene-2-carboxylate 85006-31-1 C7H9NO2S
3-Acetyl-2,5-dichlorothiophene 3-Acetyl-2,5-dichlorothiophene 36157-40-1 C6H4Cl2OS
Thiophene-3-ethanol Thiophene-3-ethanol 13781-67-4 C6H8OS
Thianaphthene Thianaphthene 95-15-8 C8H6S
5-CHLORO-3-METHYLBENZO[B]THIOPHENE 5-CHLORO-3-METHYLBENZO[B]THIOPHENE 19404-18-3 C9H7ClS
2-Chlorothiophene 2-Chlorothiophene 96-43-5 C4H3ClS
3-Methoxythiophene 3-Methoxythiophene 17573-92-1 C5H6OS
2,3-Dibromothiophene 2,3-Dibromothiophene 3140-93-0 C4H2Br2S
2,2'-BITHIOPHENE 2,2'-BITHIOPHENE 492-97-7 C8H6S2
2,5-Dibromothiophene 2,5-Dibromothiophene 3141-27-3 C4H2Br2S
2-Thiophenecarboxylic acid 2-Thiophenecarboxylic acid 527-72-0 C5H4O2S
3,4-Dibromothiophene 3,4-Dibromothiophene 3141-26-2 C4H2Br2S
2-Iodothiophene 2-Iodothiophene 3437-95-4 C4H3IS
5-Methyl-2-thiophenecarboxylic acid 5-Methyl-2-thiophenecarboxylic acid 1918-79-2 C6H6O2S
2-Amino-5-methyl-3-thiophenecarbonitrile 2-Amino-5-methyl-3-thiophenecarbonitrile 138564-58-6 C6H6N2S
5-Bromothiophenesulfonyl chloride 5-Bromothiophenesulfonyl chloride 55854-46-1 C4H2BrClO2S2
5-Chlorothiophene-2-sulfonamide 5-Chlorothiophene-2-sulfonamide 53595-66-7 C4H4ClNO2S2
2,5-Dichlorothiophene 2,5-Dichlorothiophene 3172-52-9 C4H2Cl2S
Tetrabromothiophene Tetrabromothiophene 3958-03-0 C4Br4S
4-Bromothiophene-2-carboxaldehyde 4-Bromothiophene-2-carboxaldehyde 18791-75-8 C5H3BrOS
3-Bromothiophene-2-carbaldehyde 3-Bromothiophene-2-carbaldehyde 930-96-1 C5H3BrOS
3-Acetylthiophene 3-Acetylthiophene 1468-83-3 C6H6OS
2-Thiopheneacetonitrile 2-Thiopheneacetonitrile 20893-30-5 C6H5NS
3-Thienylmethanol 3-Thienylmethanol 71637-34-8 C5H6OS
2-Bromo-5-methylthiophene 2-Bromo-5-methylthiophene 765-58-2 C5H5BrS
Thiophene-2-ethylamine Thiophene-2-ethylamine 30433-91-1 C6H9NS
3,4-Ethylenedioxythiophene 3,4-Ethylenedioxythiophene 126213-50-1 C6H6O2S
2,5-Dibromo-3-hexylthiophene 2,5-Dibromo-3-hexylthiophene 116971-11-0 C10H14Br2S
6-Chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide 6-Chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide 70415-50-8 C9H8ClNO5S2
3-Thiophenezoic acid 3-Thiophenezoic acid 88-13-1 C5H4O2S
2,5-DIBROMO-3-DECYLTHIOPHENE 2,5-DIBROMO-3-DECYLTHIOPHENE 158956-23-1 C14H22Br2S
5-Methylthiophene-2-carboxaldehyde 5-Methylthiophene-2-carboxaldehyde 13679-70-4 C6H6OS
5-Bromo-2-thiophenecarboxylic acid 5-Bromo-2-thiophenecarboxylic acid 7311-63-9 C5H3BrO2S
2-Thiopheneethanol 2-Thiopheneethanol 5402-55-1 C6H8OS
2-Chloro-3-methylthiophene 2-Chloro-3-methylthiophene 14345-97-2 C5H5ClS
3-Bromothiophene 3-Bromothiophene 872-31-1 C4H3BrS
2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene 2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene 1030825-20-7 C18H14BrFS
3,4-Dimethoxythiophene 3,4-Dimethoxythiophene 51792-34-8 C6H8O2S
2,5-DIBROMO-3-BUTYLTHIOPHENE 2,5-DIBROMO-3-BUTYLTHIOPHENE 116971-10-9 C8H10Br2S
5-Formyl-2-thiopheneboronic acid 5-Formyl-2-thiopheneboronic acid 4347-33-5 C5H5BO3S
3-Ethynylthiophene 3-Ethynylthiophene 67237-53-0 C6H4S
2,2':5',2''-TERTHIOPHENE 2,2':5',2''-TERTHIOPHENE 1081-34-1 C12H8S3
THIOPHENE-3,4-DICARBOXYLIC ACID THIOPHENE-3,4-DICARBOXYLIC ACID 4282-29-5 C6H4O4S
5-Bromothiophene-2-carbaldehyde 5-Bromothiophene-2-carbaldehyde 4701-17-1 C5H3BrOS
2-Bromo-3-methylthiophene 2-Bromo-3-methylthiophene 14282-76-9 C5H5BrS
2-Thiophenemethanol 2-Thiophenemethanol 636-72-6 C5H6OS
5-Bromothiophene-2-sulfonamide 5-Bromothiophene-2-sulfonamide 53595-65-6 C4H4BrNO2S2
3-Methyl-2-thiophenecarboxylic acid 3-Methyl-2-thiophenecarboxylic acid 23806-24-8 C6H6O2S
3-(Bromomethyl)-5-chlorobenzo[b]thiophene 3-(Bromomethyl)-5-chlorobenzo[b]thiophene 1198-51-2 C9H6BrClS
Thieno[3,2-b]thiophene Thieno[3,2-b]thiophene 251-41-2 C6H4S2
Tetrahydrothiophene Tetrahydrothiophene 110-01-0 C4H8S
2-Thiophenecarbonitrile 2-Thiophenecarbonitrile 1003-31-2 C5H3NS
2-bromo-3-hexylthiophene 2-bromo-3-hexylthiophene 69249-61-2 C10H15BrS
2-THENOYLACETONITRILE 2-THENOYLACETONITRILE 33898-90-7 C7H5NOS
Methyl 2,2-dithienylglycolate Methyl 2,2-dithienylglycolate 26447-85-8 C11H10O3S2
METHYL 3-AMINOTHIOPHENE-4-CARBOXYLATE HYDROCHLORIDE METHYL 3-AMINOTHIOPHENE-4-CARBOXYLATE HYDROCHLORIDE 39978-14-8 C6H8ClNO2S
	Dibenzothiophene-2-boronic acid Dibenzothiophene-2-boronic acid 668983-97-9 C12H9BO2S
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE 4506-71-2 C11H15NO2S
3,4-DIAMINOTHIOPHENE DIHYDROCHLORIDE 3,4-DIAMINOTHIOPHENE DIHYDROCHLORIDE 90069-81-1 C4H8Cl2N2S
3-Thiophenemalonic acid 3-Thiophenemalonic acid 21080-92-2 C7H6O4S
3-IODOTHIOPHENE 3-IODOTHIOPHENE 10486-61-0 C4H3IS
2,3,5-Tribromothiophene 2,3,5-Tribromothiophene 3141-24-0 C4HBr3S
3-DODECYLTHIOPHENE 3-DODECYLTHIOPHENE 104934-52-3 C16H28S
2-Ethynylthiophene 2-Ethynylthiophene 4298-52-6 C6H4S
3-Bromomethylthiophene 3-Bromomethylthiophene 34846-44-1 C5H5BrS
2,5-Dibromo-3-Dodecylthiophene 2,5-Dibromo-3-Dodecylthiophene 139100-06-4 C16H27BrS
5-Nitrothiophene-2-carboxylic acid 5-Nitrothiophene-2-carboxylic acid 6317-37-9 C5H3NO4S
2-Acetylbenzo[b]thiophene 2-Acetylbenzo[b]thiophene 22720-75-8 C10H8OS
2-Ethylthiophene 2-Ethylthiophene 872-55-9 C6H8S
2-Methoxythiophene 2-Methoxythiophene 16839-97-7 C5H6OS
2-bromo-3-octylthiophene 2-bromo-3-octylthiophene 145543-83-5 C12H19BrS
2-Thiophenecarboxylic acid hydrazide 2-Thiophenecarboxylic acid hydrazide 2361-27-5 C5H6N2OS
2-Nitrothiophene 2-Nitrothiophene 609-40-5 C4H3NO2S
3-Thiophenecarbonitrile 3-Thiophenecarbonitrile 1641-09-4 C5H3NS
2-Bromothiophene 2-Bromothiophene 1003-09-4 C4H3BrS
3-CHLOROTHIOPHENE 3-CHLOROTHIOPHENE 17249-80-8 C4H3ClS
4-KETO-4,5,6,7-TETRAHYDROTHIANAPHTHENE 4-KETO-4,5,6,7-TETRAHYDROTHIANAPHTHENE 13414-95-4 C8H8OS
5-BROMOBENZO[B]THIOPHENE 5-BROMOBENZO[B]THIOPHENE 4923-87-9 C8H5BrS
Thiophene-2-sulfonamide Thiophene-2-sulfonamide 6339-87-3 C4H5NO2S2
3-Decylthiophene 3-Decylthiophene 65016-55-9 C14H24S
Ethyl 2-thiophenecarboxylate Ethyl 2-thiophenecarboxylate 2810-04-0 C7H8O2S
5,5'-Dibromo-2,2'-bithiophene 5,5'-Dibromo-2,2'-bithiophene 4805-22-5 C8H4Br2S2
BENZO[B]THIOPHENE-2-CARBOXALDEHYDE BENZO[B]THIOPHENE-2-CARBOXALDEHYDE 3541-37-5 C9H6OS
2-Thiophenemethylamine 2-Thiophenemethylamine 27757-85-3 C5H7NS
3-Octylthiophene 3-Octylthiophene 65016-62-8 C12H20S
3-Thienylmethylamine 3-Thienylmethylamine 27757-86-4 C5H7NS
2,5-DIBROMO-3,4-DINITROTHIOPHENE 2,5-DIBROMO-3,4-DINITROTHIOPHENE 52431-30-8 C4Br2N2O4S
5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE 5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE 42518-98-9 C5H2Cl2OS
3-Bromo-2-chlorothiophene 3-Bromo-2-chlorothiophene 40032-73-3 C4H2BrClS
4-Bromo-2-thiophenecarboxylic acid 4-Bromo-2-thiophenecarboxylic acid 16694-18-1 C5H3BrO2S
2,5-DIBROMOTHIENO[3,2-B]THIOPHENE 2,5-DIBROMOTHIENO[3,2-B]THIOPHENE 25121-87-3 C6H2Br2S2
3,6-DIBROMOTHIENO[3,2-B]THIOPHENE 3,6-DIBROMOTHIENO[3,2-B]THIOPHENE 392662-65-6 C6H2Br2S2
2-ACETYL-5-CHLOROTHIOPHENE 2-ACETYL-5-CHLOROTHIOPHENE 6310-09-4 C6H5ClOS
2,5-Dibromo-3-octylthiophene 2,5-Dibromo-3-octylthiophene 149703-84-4 C12H18Br2S
1-(5-Methyl-2-thienyl)ethan-1-one 1-(5-Methyl-2-thienyl)ethan-1-one 13679-74-8 C7H8OS
3-Methyl-2-thiophenecarboxaldehyde 3-Methyl-2-thiophenecarboxaldehyde 5834-16-2 C6H6OS
3-Butylthiophene 3-Butylthiophene 34722-01-5 C8H12S
3-Bromothiophene-2-carboxylic acid 3-Bromothiophene-2-carboxylic acid 7311-64-0 C5H3BrO2S
Thianaphthene-2-carboxylic acid Thianaphthene-2-carboxylic acid 6314-28-9 C9H6O2S
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