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Thiophene compounds

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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.

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:
3-Hexylthiophene
CAS:
1693-86-3
MF:
C10H16S
Structure:
Chemical Name:
Methyl 3-amino-4-methylthiophene-2-carboxylate
CAS:
85006-31-1
MF:
C7H9NO2S
Structure:
Chemical Name:
3-Acetyl-2,5-dichlorothiophene
CAS:
36157-40-1
MF:
C6H4Cl2OS
Structure:
Chemical Name:
Thiophene-3-ethanol
CAS:
13781-67-4
MF:
C6H8OS
Structure:
Chemical Name:
Thianaphthene
CAS:
95-15-8
MF:
C8H6S
Structure:
Chemical Name:
5-CHLORO-3-METHYLBENZO[B]THIOPHENE
CAS:
19404-18-3
MF:
C9H7ClS
Structure:
Chemical Name:
2-Chlorothiophene
CAS:
96-43-5
MF:
C4H3ClS
Structure:
Chemical Name:
3-Methoxythiophene
CAS:
17573-92-1
MF:
C5H6OS
Structure:
Chemical Name:
2,3-Dibromothiophene
CAS:
3140-93-0
MF:
C4H2Br2S
Structure:
Chemical Name:
2,2'-BITHIOPHENE
CAS:
492-97-7
MF:
C8H6S2
Structure:
Chemical Name:
2,5-Dibromothiophene
CAS:
3141-27-3
MF:
C4H2Br2S
Structure:
Chemical Name:
2-Thiophenecarboxylic acid
CAS:
527-72-0
MF:
C5H4O2S
Structure:
Chemical Name:
3,4-Dibromothiophene
CAS:
3141-26-2
MF:
C4H2Br2S
Structure:
Chemical Name:
2-Iodothiophene
CAS:
3437-95-4
MF:
C4H3IS
Structure:
Chemical Name:
5-Methyl-2-thiophenecarboxylic acid
CAS:
1918-79-2
MF:
C6H6O2S
Structure:
Chemical Name:
2-Amino-5-methyl-3-thiophenecarbonitrile
CAS:
138564-58-6
MF:
C6H6N2S
Structure:
Chemical Name:
5-Bromothiophenesulfonyl chloride
CAS:
55854-46-1
MF:
C4H2BrClO2S2
Structure:
Chemical Name:
5-Chlorothiophene-2-sulfonamide
CAS:
53595-66-7
MF:
C4H4ClNO2S2
Structure:
Chemical Name:
2,5-Dichlorothiophene
CAS:
3172-52-9
MF:
C4H2Cl2S
Structure:
Chemical Name:
Tetrabromothiophene
CAS:
3958-03-0
MF:
C4Br4S
Structure:
Chemical Name:
4-Bromothiophene-2-carboxaldehyde
CAS:
18791-75-8
MF:
C5H3BrOS
Structure:
Chemical Name:
3-Bromothiophene-2-carbaldehyde
CAS:
930-96-1
MF:
C5H3BrOS
Structure:
Chemical Name:
3-Acetylthiophene
CAS:
1468-83-3
MF:
C6H6OS
Structure:
Chemical Name:
2-Thiopheneacetonitrile
CAS:
20893-30-5
MF:
C6H5NS
Structure:
Chemical Name:
3-Thienylmethanol
CAS:
71637-34-8
MF:
C5H6OS
Structure:
Chemical Name:
2-Bromo-5-methylthiophene
CAS:
765-58-2
MF:
C5H5BrS
Structure:
Chemical Name:
Thiophene-2-ethylamine
CAS:
30433-91-1
MF:
C6H9NS
Structure:
Chemical Name:
3,4-Ethylenedioxythiophene
CAS:
126213-50-1
MF:
C6H6O2S
Structure:
Chemical Name:
2,5-Dibromo-3-hexylthiophene
CAS:
116971-11-0
MF:
C10H14Br2S
Structure:
Chemical Name:
6-Chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide
CAS:
70415-50-8
MF:
C9H8ClNO5S2
Structure:
Chemical Name:
3-Thiophenezoic acid
CAS:
88-13-1
MF:
C5H4O2S
Structure:
Chemical Name:
2,5-DIBROMO-3-DECYLTHIOPHENE
CAS:
158956-23-1
MF:
C14H22Br2S
Structure:
Chemical Name:
5-Methylthiophene-2-carboxaldehyde
CAS:
13679-70-4
MF:
C6H6OS
Structure:
Chemical Name:
5-Bromo-2-thiophenecarboxylic acid
CAS:
7311-63-9
MF:
C5H3BrO2S
Structure:
Chemical Name:
2-Thiopheneethanol
CAS:
5402-55-1
MF:
C6H8OS
Structure:
Chemical Name:
2-Chloro-3-methylthiophene
CAS:
14345-97-2
MF:
C5H5ClS
Structure:
Chemical Name:
3-Bromothiophene
CAS:
872-31-1
MF:
C4H3BrS
Structure:
Chemical Name:
2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene
CAS:
1030825-20-7
MF:
C18H14BrFS
Structure:
Chemical Name:
3,4-Dimethoxythiophene
CAS:
51792-34-8
MF:
C6H8O2S
Structure:
Chemical Name:
5-Formyl-2-thiopheneboronic acid
CAS:
4347-33-5
MF:
C5H5BO3S
Structure:
Chemical Name:
2,2':5',2''-TERTHIOPHENE
CAS:
1081-34-1
MF:
C12H8S3
Structure:
Chemical Name:
5-Bromothiophene-2-carbaldehyde
CAS:
4701-17-1
MF:
C5H3BrOS
Structure:
Chemical Name:
2-Bromo-3-methylthiophene
CAS:
14282-76-9
MF:
C5H5BrS
Structure:
Chemical Name:
2,5-Dibromo-3-octylthiophene
CAS:
149703-84-4
MF:
C12H18Br2S
Structure:
Chemical Name:
1-(5-Methyl-2-thienyl)ethan-1-one
CAS:
13679-74-8
MF:
C7H8OS
Structure:
Chemical Name:
3-Methyl-2-thiophenecarboxaldehyde
CAS:
5834-16-2
MF:
C6H6OS
Structure:
Chemical Name:
2-Thiophenemethanol
CAS:
636-72-6
MF:
C5H6OS
Structure:
Chemical Name:
5-Bromothiophene-2-sulfonamide
CAS:
53595-65-6
MF:
C4H4BrNO2S2
Structure:
Chemical Name:
3-Methyl-2-thiophenecarboxylic acid
CAS:
23806-24-8
MF:
C6H6O2S
Structure:
Chemical Name:
3-(Bromomethyl)-5-chlorobenzo[b]thiophene
CAS:
1198-51-2
MF:
C9H6BrClS
Structure:
Chemical Name:
Thieno[3,2-b]thiophene
CAS:
251-41-2
MF:
C6H4S2
Structure:
Chemical Name:
Tetrahydrothiophene
CAS:
110-01-0
MF:
C4H8S
Structure:
Chemical Name:
2-Thiophenecarbonitrile
CAS:
1003-31-2
MF:
C5H3NS
Structure:
Chemical Name:
2-bromo-3-hexylthiophene
CAS:
69249-61-2
MF:
C10H15BrS
Structure:
Chemical Name:
2-THENOYLACETONITRILE
CAS:
33898-90-7
MF:
C7H5NOS
Structure:
Chemical Name:
Methyl 2,2-dithienylglycolate
CAS:
26447-85-8
MF:
C11H10O3S2
Structure:
Chemical Name:
METHYL 3-AMINOTHIOPHENE-4-CARBOXYLATE HYDROCHLORIDE
CAS:
39978-14-8
MF:
C6H8ClNO2S
Structure:
Chemical Name:
Dibenzothiophene-2-boronic acid
CAS:
668983-97-9
MF:
C12H9BO2S
Structure:
Chemical Name:
ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE
CAS:
4506-71-2
MF:
C11H15NO2S
Structure:
Chemical Name:
3,4-DIAMINOTHIOPHENE DIHYDROCHLORIDE
CAS:
90069-81-1
MF:
C4H7ClN2S
Structure:
Chemical Name:
3-Thiophenemalonic acid
CAS:
21080-92-2
MF:
C7H6O4S
Structure:
Chemical Name:
3-IODOTHIOPHENE
CAS:
10486-61-0
MF:
C4H3IS
Structure:
Chemical Name:
2,3,5-Tribromothiophene
CAS:
3141-24-0
MF:
C4HBr3S
Structure:
Chemical Name:
3-DODECYLTHIOPHENE
CAS:
104934-52-3
MF:
C16H28S
Structure:
Chemical Name:
2-Ethynylthiophene
CAS:
4298-52-6
MF:
C6H4S
Structure:
Chemical Name:
3-Bromomethylthiophene
CAS:
34846-44-1
MF:
C5H5BrS
Structure:
Chemical Name:
2,5-Dibromo-3-Dodecylthiophene
CAS:
139100-06-4
MF:
C16H27BrS
Structure:
Chemical Name:
5-Nitrothiophene-2-carboxylic acid
CAS:
6317-37-9
MF:
C5H3NO4S
Structure:
Chemical Name:
2-Acetylbenzo[b]thiophene
CAS:
22720-75-8
MF:
C10H8OS
Structure:
Chemical Name:
2-Ethylthiophene
CAS:
872-55-9
MF:
C6H8S
Structure:
Chemical Name:
2-Methoxythiophene
CAS:
16839-97-7
MF:
C5H6OS
Structure:
Chemical Name:
2-bromo-3-octylthiophene
CAS:
145543-83-5
MF:
C12H19BrS
Structure:
Chemical Name:
2-Thiophenecarboxylic acid hydrazide
CAS:
2361-27-5
MF:
C5H6N2OS
Structure:
Chemical Name:
2-Nitrothiophene
CAS:
609-40-5
MF:
C4H3NO2S
Structure:
Chemical Name:
3-Thiophenecarbonitrile
CAS:
1641-09-4
MF:
C5H3NS
Structure:
Chemical Name:
2-Bromothiophene
CAS:
1003-09-4
MF:
C4H3BrS
Structure:
Chemical Name:
3-CHLOROTHIOPHENE
CAS:
17249-80-8
MF:
C4H3ClS
Structure:
Chemical Name:
4-KETO-4,5,6,7-TETRAHYDROTHIANAPHTHENE
CAS:
13414-95-4
MF:
C8H8OS
Structure:
Chemical Name:
5-BROMOBENZO[B]THIOPHENE
CAS:
4923-87-9
MF:
C8H5BrS
Structure:
Chemical Name:
Thiophene-2-sulfonamide
CAS:
6339-87-3
MF:
C4H5NO2S2
Structure:
Chemical Name:
3-Decylthiophene
CAS:
65016-55-9
MF:
C14H24S
Structure:
Chemical Name:
Ethyl 2-thiophenecarboxylate
CAS:
2810-04-0
MF:
C7H8O2S
Structure:
Chemical Name:
5,5'-Dibromo-2,2'-bithiophene
CAS:
4805-22-5
MF:
C8H4Br2S2
Structure:
Chemical Name:
BENZO[B]THIOPHENE-2-CARBOXALDEHYDE
CAS:
3541-37-5
MF:
C9H6OS
Structure:
Chemical Name:
2-Thiophenemethylamine
CAS:
27757-85-3
MF:
C5H7NS
Structure:
Chemical Name:
3-Octylthiophene
CAS:
65016-62-8
MF:
C12H20S
Structure:
Chemical Name:
3-Thienylmethylamine
CAS:
27757-86-4
MF:
C5H7NS
Structure:
Chemical Name:
2,5-DIBROMO-3,4-DINITROTHIOPHENE
CAS:
52431-30-8
MF:
C4Br2N2O4S
Structure:
Chemical Name:
5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE
CAS:
42518-98-9
MF:
C5H2Cl2OS
Structure:
Chemical Name:
3-Bromo-2-chlorothiophene
CAS:
40032-73-3
MF:
C4H2BrClS
Structure:
Chemical Name:
4-Bromo-2-thiophenecarboxylic acid
CAS:
16694-18-1
MF:
C5H3BrO2S
Structure:
Chemical Name:
2,5-DIBROMOTHIENO[3,2-B]THIOPHENE
CAS:
25121-87-3
MF:
C6H2Br2S2
Structure:
Chemical Name:
3,6-DIBROMOTHIENO[3,2-B]THIOPHENE
CAS:
392662-65-6
MF:
C6H2Br2S2
Structure:
Chemical Name:
2-ACETYL-5-CHLOROTHIOPHENE
CAS:
6310-09-4
MF:
C6H5ClOS
Structure:
Chemical Name:
2,5-DIBROMO-3-BUTYLTHIOPHENE
CAS:
116971-10-9
MF:
C8H10Br2S
Structure:
Chemical Name:
3-Ethynylthiophene
CAS:
67237-53-0
MF:
C6H4S
Structure:
Chemical Name:
Thiophene-3,4-dicarboxylic acid
CAS:
4282-29-5
MF:
C6H4O4S
Structure:
Chemical Name:
3-Butylthiophene
CAS:
34722-01-5
MF:
C8H12S
Structure:
Chemical Name:
3-Bromothiophene-2-carboxylic acid
CAS:
7311-64-0
MF:
C5H3BrO2S
Structure:
Chemical Name:
Thianaphthene-2-carboxylic acid
CAS:
6314-28-9
MF:
C9H6O2S