Thiophenes

Thiophenes (thiofurans) are important sulfur-containing heterocyclic compounds that function as analogues of furans and pyrroles, and are widely used as building blocks in many agrochemicals and pharmaceuticals as well as materials science. Benzothiophene and dibenzothiophene contain the thiophene ring fused with one and two benzene rings, respectively. As a consequence of its aromaticity, thiophene does not exhibit the same properties seen for conventional thioethers. For example, the sulfur atom in a thiophene resists alkylation and oxidation. Thiophene can also serve as a bioisostere of the benzene ring, such as in the NSAID lornoxicam, the thiophene analog of piroxicam. The presence of a halogen allows these reagents to be used as substrates in various coupling reactions, including Suzuki-Miyaura cross-coupling reactions.

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New Reagents for Selective Metalation, Deprotonation, and Additions

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T5400 Tetrabromothiophene ReagentPlus®, 99% C4Br4S
131873 Tetrachlorothiophene 99% C4Cl4S
172758 2,3,5-Tribromothiophene 96% C4HBr3S
544280 2,5-Dichlorothiophene-3-sulfonyl chloride 97% C4HCl3O2S2
650285 4,5-Dichlorothiophene-2-sulfonyl chloride 97% C4HCl3O2S2
636223 5-Bromothiophene-2-sulfonyl chloride 97% C4H2BrClO2S2
329762 2-Bromo-5-chlorothiophene 98% C4H2BrClS
544531 2-Bromo-5-nitrothiophene 97% C4H2BrNO2S
D43905 2,3-Dibromothiophene 97% C4H2Br2S
759325 2,4-Dibromothiophene C4H2Br2S
108472 2,5-Dibromothiophene 95% C4H2Br2S
247154 3,4-Dibromothiophene 99% C4H2Br2S
544272 5-Chlorothiophene-2-sulfonyl chloride 96% C4H2Cl2O2S2
650293 2,3-Dichlorothiophene C4H2Cl2S
D75807 2,5-Dichlorothiophene 98% C4H2Cl2S
331570 2,5-Diiodothiophene 98% C4H2I2S
124168 2-Bromothiophene 98% C4H3BrS
106224 3-Bromothiophene 97% C4H3BrS
155667 2-Chlorothiophene 96% C4H3ClS
341061 3-Chlorothiophene 98% C4H3ClS
542768 2,5-Dichlorothiophene-3-sulfonamide 97% C4H3Cl2NO2S2
651893 4,5-Dichlorothiophene-2-sulfonamide C4H3Cl2NO2S2
196150 2-Iodothiophene 98% C4H3IS
215023 3-Iodothiophene ≥97% C4H3IS
542741 5-Bromothiophene-2-sulfonamide 97% C4H4BrNO2S2
542695 5-Chlorothiophene-2-sulfonamide 97% C4H4ClNO2S2
CBR01142 3-Chloro-2,3-dihydrothiophene 1,1-dioxide AldrichCPR C4H5ClO2S
CDS005108 1,1-dioxo-2,5-dihydro-1H-1lambda6-thiophene-3-sulfonyl chloride AldrichCPR C4H5ClO4S2
CBR00934 (1,1-Dioxido-2,3-dihydro-3-thienyl)amine hydrochloride AldrichCPR C4H8ClNO2S
CBR00743 3-(Hydroxyamino)tetrahydrothiophene 1,1-dioxide hydrochloride AldrichCPR C4H10ClNO3S
CDS013861 4-bromo-2-thiophenecarbonyl chloride AldrichCPR C5H2BrClOS
CDS003609 4-bromothiophene-2-carbonitrile AldrichCPR C5H2BrNS
731315 4-Bromothiophene-3-carbonitrile 97% C5H2BrNS
574430 5-Bromothiophene-2-carbonitrile 97% C5H2BrNS
764515 2,5-Dibromothiophene-3-carboxaldehyde 97% C5H2Br2OS
707090 3,4-Dibromothiophene-2-carboxaldehyde 97% C5H2Br2OS
753351 3,5-Dibromothiophene-2-carboxylic acid 95% C5H2Br2O2S
665983 5-Chloro-2-thiophenecarbonitrile 97% C5H2ClNS
CDS013694 3-chlorothiophene-2-carbonyl chloride AldrichCPR C5H2Cl2OS
654795 2,5-Dichlorothiophene-3-carboxylic acid 97% C5H2Cl2O2S
CDS015492 2-bromothiophene-3-carbaldehyde AldrichCPR C5H3BrOS
283452 4-Bromo-2-thiophenecarboxaldehyde 90% C5H3BrOS
152625 5-Bromo-2-thiophenecarboxaldehyde 95% C5H3BrOS
638129 2-Bromo-3-thiophenecarboxylic acid 97% C5H3BrO2S
633011 3-Bromothiophene-2-carboxylic acid 97% C5H3BrO2S
732214 4-Bromo-3-thiophenecarboxylic acid 97% C5H3BrO2S
467944 5-Bromo-2-thiophenecarboxylic acid 97% C5H3BrO2S
CDS013228 5-bromothiophene-3-carboxylic acid AldrichCPR C5H3BrO2S
443239 5-Chloro-2-thiophenecarboxaldehyde 97% C5H3ClOS
586994 3-Chlorothiophene-2-carboxylic acid 97% C5H3ClO2S
633003 5-Chlorothiophene-2-carboxylic acid 97% C5H3ClO2S
CBR01287 4-Bromo-2-thiophenecarboxamide AldrichCPR C5H4BrNOS
732222 4-Bromothiophene-3-carboxamide 97% C5H4BrNOS
CBR00204 5-Bromo-2-thiophenecarboxamide AldrichCPR C5H4BrNOS
700282 2,3-Dibromo-4-methylthiophene 97% C5H4Br2S
716375 2,5-Dibromo-3-methylthiophene 97% C5H4Br2S
692069 2-Bromo-3-(bromomethyl)thiophene 96% C5H4Br2S
668362 2,5-Dichloro-3-methylthiophene 96% C5H4Cl2S
241822 2-Chloro-5-(chloromethyl)thiophene 97% C5H4Cl2S
CDS016046 (4-bromo-2-thienyl)methanol AldrichCPR C5H5BrOS
337021 2-Bromo-3-methylthiophene 95% C5H5BrS
515485 2-Bromo-5-methylthiophene 95% C5H5BrS
474991 3-Bromo-4-methylthiophene 95% C5H5BrS
648728 4-Bromo-2-methylthiophene 97% C5H5BrS
678619 5-Chlorothiophene-2-carboxylic acid hydrazide 97% C5H5ClN2OS
648760 2-Chloro-3-methylthiophene 97% C5H5ClS
460532 2-Iodo-5-methylthiophene 97% C5H5IS
729248 3-(Aminomethyl)-2-bromothiophene 95% C5H6BrNS
CDS007961 5-bromothiophen-2-ylmethylamine AldrichCPR C5H6BrNS
CDS013426 (5-chlorothien-2-yl)methylamine hydrochloride AldrichCPR C5H7Cl2NS
CBR01534 (2-Thienylmethyl)hydrazine hydrochloride AldrichCPR C5H9ClN2S
696722 3,4-Dibromothiophene-2,5-dicarboxaldehyde 97% C6H2Br2O2S
708283 5-Fluoro-2,3-thiophenedicarboxaldehyde 97% C6H3FO2S
CDS014953 2-bromo-1-(3-chloro-2-thienyl)-1-ethanone AldrichCPR C6H4BrClOS
CDS003755 2-bromo-1-(5-chloro-thiophen-2-yl)-ethanone AldrichCPR C6H4BrClOS
CDS008156 3-bromo-4-fluorothiophenol AldrichCPR C6H4BrFS
CDS003130 (4-Bromo-thiophen-2-yl)-acetonitrile AldrichCPR C6H4BrNS
CFSS0002 2-(2,2-dibromovinyl)thiophene AldrichCPR C6H4Br2S
439509 3-Acetyl-2,5-dichlorothiophene 98% C6H4Cl2OS
CDS011187 2,5-difluoro thiophenol AldrichCPR C6H4F2S
CDS003868 3,5-difluorothiophenol AldrichCPR C6H4F2S
595594 2-(2-Bromoacetyl)thiophene 97% C6H5BrOS
633054 2-Acetyl-3-bromothiophene 97% C6H5BrOS
329738 2-Acetyl-5-bromothiophene 99% C6H5BrOS
738336 3-(Bromoacetyl)thiophene 97% C6H5BrOS
776955 4-Bromo-3-methylthiophene-2-carboxaldehyde 97% C6H5BrOS
CDS005911 methyl 4-bromothiophene-2-carboxylate AldrichCPR C6H5BrO2S
247073 2-Acetyl-5-chlorothiophene 99% C6H5ClOS
CDS015144 5-chloro-4-methoxythiophene-3-carboxylic acid AldrichCPR C6H5ClO3S
579637 2-Acetyl-5-iodothiophene 97% C6H5IOS
758221 (Z)-(5-Bromo-2-thienyl)ethanone oxime 97% C6H6BrNOS
CBR01581 5-[(Methylamino)carbonyl]-3-thiophenesulfonyl chloride AldrichCPR C6H6ClNO3S2
738298 2-Bromo-3,5-dimethylthiophene contains sodium bicarbonate as stabilizer, 96% C6H7BrS
749567 4-Bromo-2,3-dimethylthiophene 97% C6H7BrS
CBR01785 3-(2-Bromoethyl)tetrahydrothiophene 1,1-dioxide AldrichCPR C6H11BrO2S
CDS004813 4-trifluoromethyl-2,3,5,6-tetrafluorothiophenol AldrichCPR C7HF7S
CBR01621 4-(5-Isoxazolyl)-2-thiophenesulfonyl chloride AldrichCPR C7H4ClNO3S2
728667 trans-3-(4-Bromothiophen-2-yl)acrylic acid 97% C7H5BrO2S
CDS007567 4-(trifluoromethyl)thiophenol AldrichCPR C7H5F3S
CBR01166 1-(5-Bromo-2-thienyl)propan-1-one AldrichCPR C7H7BrOS
CBR01251 1-[4-(Chloromethyl)-2-thienyl]ethanone AldrichCPR C7H7ClOS
CDS013276 ([(5-chlorothien-2-yl)methyl]sulfonyl)acetic acid AldrichCPR C7H7ClO4S2
CBR00942 (Methylamino)(2-thienyl)acetic acid hydrochloride AldrichCPR C7H10ClNO2S
CBR01263 N-Methyl-1-(2-thienyl)ethanamine hydrochloride AldrichCPR C7H12ClNS
CBR01050 2-(3-Methyl-2-thienyl)ethanamine hydrochloride hydrate AldrichCPR C7H14ClNOS
515493 5,5′-Dibromo-2,2′-bithiophene 99% C8H4Br2S2
522856 5-Bromo-2,2′-bithiophene 96% C8H5BrS2
CDS012377 4-(5-bromothien-2-yl)butanoic acid AldrichCPR C8H9BrO2S
CBR00838 4-Methyl-3-(2-thienyl)-1H-pyrazol-5-amine hydrochloride AldrichCPR C8H10ClN3S
CBR00906 1-(2-Thienyl)-1-butanamine hydrochloride AldrichCPR C8H14ClNS
777056 5′-Bromo-2,2′-bithiophene-5-carboxaldehyde 97% C9H5BrOS2
CDS014012 2,2′-bithiophene-5-carbonyl chloride AldrichCPR C9H5ClOS2
762644 3-(Boc-amino)-2-bromothiophene 97% C9H12BrNO2S
596663 2-(4-Bromophenyl)thiophene 97% C10H7BrS
759708 2-[(Boc-amino)methyl]-5-bromothiophene 96% C10H14BrNO2S
CBR00781 Piperidin-3-yl(2-thienyl)methanone hydrochloride AldrichCPR C10H14ClNOS
764140 2-Bromo-4-hexylthiophene 97% C10H15BrS
694258 5-Bromo-2-hexylthiophene 97% C10H15BrS
CDS011721 5-(4-chlorophenyl)thiophene-2-carbaldehyde AldrichCPR C11H7ClOS
CDS006076 5-(2-fluoro-phenyl)-thiophene-2-carbaldehyde AldrichCPR C11H7FOS
649406 2-Amino-3-(4-bromobenzoyl)thiophene 97% C11H8BrNOS
649430 5-(4-Bromophenyl)thiophene-2-carboxylic hydrazide 95% C11H9BrN2OS
699098 5,5′′-Dibromo-2,2′:5′,2′′-terthiophene 97% C12H6Br2S3
714550 2-Bromo-3-octylthiophene 95% C12H19BrS
649384 Ethyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate 97% C13H12ClNO2S
739375 5-Bromo-5′-hexyl-2,2′-bithiophene 98% C14H17BrS2
688312 2-Bromo-3-dodecylthiophene 95% C16H27BrS