76536-95-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Thienyl isocyanate is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its reactive nature and ability to form heterocyclic structures, which are often found in drug molecules.
Used in Agrochemical Industry:
3-Thienyl isocyanate is employed as a building block in the development of agrochemicals, such as pesticides and herbicides, where its reactive properties allow for the creation of novel and effective molecules.
Used in Material Science:
3-Thienyl isocyanate is used as a precursor in the development of new materials with applications in electronic devices and sensors, leveraging its ability to form heterocyclic compounds and participate in Diels-Alder reactions.
Used in Polymer and Surface Functionalization:
3-Thienyl isocyanate is used as a coupling agent for the functionalization of polymers and surfaces, enabling the design and modification of advanced materials with tailored properties for specific applications.

InChI:InChI=1/C5H3NOS/c7-4-6-5-1-2-8-3-5/h1-3H

Upstream product

• 41507-35-1 3-thiophene carboxylic acid chloride 
• 4648-54-8 trimethylsilylazide 
• 88-13-1 3-Thiophene carboxylic acid 

Downstream Products

• 935660-78-9 N-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-N'-thiophen-3-ylurea 
• 1173206-08-0 1-{4-[7-morpholin-4-yl-3-(2,2,2-trifluoroethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]phenyl}-3-(3-thienyl)urea 
• 480993-88-2 [4-(2,3,4,5-tetrahydro-1,3-dimethyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyl]methyl thiophen-3-ylcarbamate 
• 1165949-54-1 [4-(2,3,4,5-tetrahydro-2,4-dioxo-1,3-dipropyl-1H-pyrrolo[3,2-d]pyrimidin-6-yl)phenyl]methyl thiophen-3-ylcarbamate 
• 1241906-57-9 sodium [(2,3-difluorobenzyl) 5-acetamido-9-(4-chlorobenzamido)-3,5,9-trideoxy-7,8-O-isopropylidene-4-O-(3-thienylcarbamoyl)-D-glycero-α-D-galacto-2-nonulopyranosid]onate 
• 1386975-88-7 1-[3-(3,5-dichloro-benzylamino)propyl]-3-thiophen-3-yl-urea 
• 1452394-95-4 C₁₈H₂₁N₃O₃S 
• 1452394-50-1 C₁₇H₁₈N₄OS 
• 1452394-35-2 C₁₈H₂₁N₃O₂S 
• 1386975-89-8 1-[3-(3-chloro-5-methoxy-benzylamino)propyl]-3-(thiophen-3-yl)urea 
• 1381805-10-2 C₁₈H₁₃N₃O₂S₂ 
• 1334400-26-8 C₁₁H₁₁N₃OS 
• 1237785-67-9 C₂₀H₂₁N₇O₂S 

Relevant academic research and scientific papers

ISOINDOLINONE COMPOUNDS

Disclosed herein is a compound or pharmaceutically acceptable salts or stereoisomers thereof of of formula I wherein X1 is linear or branched C1-6 alkyl, C3-6 cycloalkyl, -C1-6 alkyl C3-6 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, C1-6 alkyl C6-10 aryl, C1-6 alkyl 5-10 membered heteroaryl, wherein X1 is unsubstituted or substituted with one or more of halogen, linear or branched C1-6 alkyl, linear or branched C1-6 heteroalkyl, CF3, CHF2, -O-CHF2, -O-(CH2)2-OMe, OCF3, C1-6 alkylamino, -CN, -N(H)C(O)-C1- 6alkyl, -OC(O)-C1-6alkyl, -OC(O)-C1-4alkylamino, -C(O)O-C1-6alkyl, -COOH, - CHO, -C1-6alkylC(O)OH, -C1-6alkylC(O)O-C1-6alkyl, NH2, C1-6 alkoxy or C1-6 alkylhydroxy; X2 is hydrogen, C6-10 aryl, 5-10 membered heteroaryl, -O-(5-10 membered heteroaryl), 4-8 membered heterocycloalkyl, C1-4 alkyl 4-8 membered heterocycloalkyl, -O-(4-8 membered heterocycloalkyl), -O-C1-4 alkyl-(4-8 membered heterocycloalkyl), -OC(O)-C1-4alkyl-4-8 membered heterocycloalkyl or C6 aryloxy, wherein X2 is unsubstituted or substituted with one or more of linear or branched C1-6 alkyl, NH2, NMe2 or 5-6 membered heterocycloalkyl; n is 0, 1 or 2.

2-Arylureidobenzoic Acids: Selective Noncompetitive Antagonists for the Homomeric Kainate Receptor Subtype GluR5

A series of 2-arylureidobenzoic acids (AUBAs) was prepared by a short and effective synthesis, and the pharmacological activity at glutamate receptors was evaluated in vitro and in vivo. The compounds showed noncompetitive antagonistic activity at the kainate receptor subtype GluR5. The most potent compounds showed more than 50-fold selectivity for GluR5 compared to GluR6 and the AMPA receptor subtypes GluR1-4. The structure-activity relationships for the AUBAs showed distinct structural requirements for the substituents on the two aromatic ring systems. Only para-substituents were tolerated on the benzoic acid moiety (ring A), whereas ring B tolerated a variety of substituents, but with a preference for lipophilic substituents. The most potent compounds had a 4-chloro substituent on ring A and 3-chlorobenzene (6b), 2-naphthalene (8h), or 2-indole (8k) as ring B and had IC50 values of 1.3, 1.2, and 1.2 μM, respectively, in a functional GluR5 assay. Compound 6c (IC50 = 4.8 μM at GluR5) showed activity in the in vivo ATPA rigidity test, indicating that 6c has better pharmacokinetic properties than 8h, which was inactive in this test. The AUBAs are the first example of a series of noncompetitive GluR5-selective antagonists and may prove to be important pharmacological tools and leads in the search for therapeutic glutamatergic agents.

Preparation and Cycloaddition of Thienyl Isocyanates with Trimethylsilyl Azide: One-pot Synthesis of Thienyltetrazolin-5-ones

Efforts to prepare thienyl isocyanates by thermal reactions of thenoyl chlorides with trimethylsilyl azide (TMSA) led preferentially to the formation of 1,4-disubstituted tetrazolin-5-ones, arising by interaction of the initially formed thienyl isocyanate with TMSA.In fact, 2-thenoyl chloride and benzothiophene-2-carbonyl chloride reacted with 1 equiv.TMSA in refluxing carbon tetrachloride to give 1-(2-thienyl or benzothienyl)-4-(2-thenoyl or benzothiophenecarbonyl)tetrazolin-5-one 4d, e, whereas 3-thenoyl chloride led to 1-(3-thienyl)-4-trimethylsilyltetrazolin-5-one adduct II which was converted, after hydrolytic desilylation, to 1-(3-thienyl)tetrazolin-5(4H)-one 4c.Similar reactions, carried out with more than two equiv. of TMSA, led in all cases to the formation of the corresponding 1-heteroaryltetrazolin-5-one 4a-c via the corresponding silylated tetrazolin-5-ones II, whereas at room temp. such reactions gave essentially thenoyl azides which, after elimination of the excess TMSA, were thermally converted to the corresponding thienyl isocyanates 3 in fairly good yields.