76536-95-3

Basic information

• Product Name: 3-Thienyl isocyanate
• Synonyms: 3-THIENYL ISOCYANATE;3-ISOCYANATOTHIOPHENE;Thiophene, 3-isocyanato- (9CI);3-THIENYL ISOCYANATE, 98+%;Thien-3-yl isocyanate
• CAS NO: 76536-95-3
• Molecular Formula: C₅H₃NOS
• Molecular Weight: 125.15
• Product Categories: ISOCYANATE;Isocyanates;Thiophenes & Benzothiophenes;Thiophenes & Benzothiophenes
• Mol File: 76536-95-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 36 °C
• Flash Point: 51.5°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 2.27mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: 3-Thienyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thienyl isocyanate(76536-95-3)
• EPA Substance Registry System: 3-Thienyl isocyanate(76536-95-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-3
• RIDADR: 2206
• Hazardous Substances Data: 76536-95-3(Hazardous Substances Data)

Usage

General Description

3-Thienyl isocyanate is a chemical compound with the formula C5H3NOS. It is a reactive and versatile building block in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and materials. 3-Thienyl isocyanate is a potent dienophile and undergoes Diels-Alder reactions with electron-rich dienes. It is also used as a reagent for the synthesis of heterocyclic compounds and has been studied for its potential as a precursor in the development of new materials with applications in electronic devices and sensors. Additionally, 3-Thienyl isocyanate can be employed as a coupling agent for the functionalization of polymers and surfaces, making it a valuable tool in the design and modification of advanced materials.

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

• 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 
• 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 
• 1386975-88-7 1-[3-(3,5-dichloro-benzylamino)propyl]-3-thiophen-3-yl-urea 
• 1381805-10-2 C₁₈H₁₃N₃O₂S₂ 
• 1334400-26-8 C₁₁H₁₁N₃OS 
• 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 
• 1237785-67-9 C₂₀H₂₁N₇O₂S 
• 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 
• 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 
• 935660-78-9 N-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-N'-thiophen-3-ylurea 

Relevant articles and documents

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.

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.