2-Thiophenecarbonyl chloride CAS 5271-67-0
2-Thiophenecarbonyl chloride Basic information
| Product Name: | 2-Thiophenecarbonyl chloride |
| Synonyms: | AKOS 92490;AKOS BBS-00003924;ALPHA-THENOYL CHLORIDE;THIOPHENE-2-CARBOXYLIC ACID CHLORIDE;THIOPHENE-2-CARBONYL CHLORIDE;TIMTEC-BB SBB004099;2-Thiophenzoyl Chloride;2-thienylcarbonyl chloride |
| CAS: | 5271-67-0 |
| MF: | C5H3ClOS |
| MW: | 146.59 |
| EINECS: | 226-092-4 |
| Product Categories: | Building Blocks;C4 to C6;ACIDHALIDE;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes;Thiophene&Benzothiophene;Heterocyclic Compounds |
| Mol File: | 5271-67-0.mol |
2-Thiophenecarbonyl chloride Chemical Properties
| Boiling point | 206-208 °C (lit.) |
| density | 1.371 g/mL at 25 °C (lit.) |
| refractive index | n |
| Fp | 195 °F |
| storage temp. | 2-8°C |
| solubility | Chloroform |
| form | Liquid |
| color | Clear colorless to yellow-gray |
| Specific Gravity | 1.371 |
| Sensitive | Moisture Sensitive |
| BRN | 110145 |
| InChI | 1S/C5H3ClOS/c6-5(7)4-2-1-3-8-4/h1-3H |
| InChIKey | QIQITDHWZYEEPA-UHFFFAOYSA-N |
| SMILES | ClC(=O)c1cccs1 |
| CAS DataBase Reference | 5271-67-0(CAS DataBase Reference) |
| NIST Chemistry Reference | 2-Thiophenecarbonyl chloride(5271-67-0) |
| EPA Substance Registry System | 2-Thiophenecarbonyl chloride (5271-67-0) |
Safety Information
| Hazard Codes | C |
| Risk Statements | 34-37 |
| Safety Statements | 26-36/37/39-45 |
| RIDADR | UN 3265 8/PG 2 |
| WGK Germany | 3 |
| F | 8 |
| TSCA | TSCA listed |
| HazardClass | 8 |
| PackingGroup | II |
| HS Code | 29349990 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Eye Dam. 1 Met. Corr. 1 Skin Corr. 1B |
| Chemical Properties | CLEAR COLOURLESS TO YELLOW-GREY LIQUID |
| Uses | 2-Thiophenecarbonyl Chloride is used in the synthesis of substituted pyridines as selective and highly effective GPR119 agonists. It is also seen in the preparation of diuretics. |
| Uses | 2-Thiophenecarbonyl chloride was used in the synthesis of building blocks derived from ornithine by undergoing acylation/sulphonation of copper complex of orthinine. |
| General Description | The postfunctionalization reaction of 2-thiophenecarbonyl chloride with single walled carbon nanotubes (SWCNTs) was studied. |
| Synthesis | 88-15-3 5271-67-0 The general procedure for the synthesis of 2-thiophenecarbonyl chloride from 2-acetylthiophene was as follows: to a mixed solution containing 2-acetylthiophene (0.108 mL, 1.0 mmol), pyridine (0.016 mL, 0.20 mmol), and chlorobenzene (0.35 mL), disulfur dichloride (S2Cl2, 0.16 mL, 2.0 mmol) was slowly added at room temperature (S2Cl2, 0.16 mL, 2.0 mmol), while stirring continuously. After the reaction mixture was stirred for 1 hour and 45 minutes, sulfuryl chloride (SO2Cl2, 0.162 mL, 2.0 mmol) was added dropwise, followed by continued stirring for 0.5 hours at room temperature. Next, the reaction mixture was heated to 132 °C and stirred at this temperature for 14 hours. Upon completion of the reaction, the reaction mixture was diluted with deuterated chloroform (CDCl3, 2 mL) and the internal standard (tributyl phosphate, 1BU3PO4, 0.0552 mL, 0.20 mmol) was added for nuclear magnetic resonance (1H NMR) analysis. The analytical results showed that the yield of 2-thiophenecarbonyl chloride was 90%. |
| References | [1] Patent: WO2017/5606, 2017, A1. Location in patent: Page/Page column 31-32 [2] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10370 - 10374 [3] Patent: WO2016/150937, 2016, A1. Location in patent: Page/Page column 27 [4] Patent: WO2016/202757, 2016, A1. Location in patent: Page/Page column 30; 31 [5] Patent: TW2017/36360, 2017, A |
2-Thiophenecarbonyl chloride Preparation Products And Raw materials
| Raw materials | 2-Acetylthiophene-->2-Thiophenecarboxylic acid-->Thiophene(SIV) (9CI)-->Oxalyl chloride-->Sulfuryl chloride-->4-Iodobenzoyl chloride-->Disulfur dichloride-->Pyridine-->2-Iodothiophene-->Terephthaloyl chloride |
| Preparation Products | ETHYL 2-[(2-THIENYLCARBONYL)AMINO]ACETATE-->2-Thienyl isocyanate-->Thiophene-2-carboxylic acid fluoride-->2-N-BUTYRYLTHIOPHENE-->tioxazafen-->2-BENZOYLTHIOPHENE-->BIS(2-THIENYL) KETONE-->2-(TRIFLUOROACETYL)THIOPHENE-->6,7-DIMETHOXY-2-(2-THIENYL)-4H-3,1-BENZOXAZIN-4-ONE-->ethyl 2-(thiophene-2-carboxamido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate |
