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2-Thiophenecarbonyl chloride

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CAS:5271-67-0
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2-Thiophenecarbonyl chloride manufacturers

  • 2-Thenoyl Chloride
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  • 2025-09-25
  • CAS:5271-67-0
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2-Thiophenecarbonyl chloride Basic information
Product Name:2-Thiophenecarbonyl chloride
Synonyms:AKOS 92490;AKOS BBS-00003924;ALPHA-THENOYL CHLORIDE;THIOPHENE-2-CARBOXYLIC ACID CHLORIDE;TIMTEC-BB SBB004099;2-Thiophenzoyl Chloride;2-thienylcarbonyl chloride;2-Thiophenecarboxylic acid chloride
CAS:5271-67-0
MF:C5H3ClOS
MW:146.59
EINECS:226-092-4
Product Categories:Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes;ACIDHALIDE;Thiophene&Benzothiophene;Heterocyclic Compounds
Mol File:5271-67-0.mol
2-Thiophenecarbonyl chloride Structure
2-Thiophenecarbonyl chloride Chemical Properties
Boiling point 206-208 °C (lit.)
density 1.371 g/mL at 25 °C (lit.)
refractive index n20/D 1.590(lit.)
Fp 195 °F
storage temp. 2-8°C
solubility Chloroform
form Liquid
color Clear colorless to yellow-gray
Specific Gravity1.371
Sensitive Moisture Sensitive
BRN 110145
InChI1S/C5H3ClOS/c6-5(7)4-2-1-3-8-4/h1-3H
InChIKeyQIQITDHWZYEEPA-UHFFFAOYSA-N
SMILESClC(=O)c1cccs1
CAS DataBase Reference5271-67-0(CAS DataBase Reference)
NIST Chemistry Reference2-Thiophenecarbonyl chloride(5271-67-0)
EPA Substance Registry System2-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
8
TSCA TSCA listed
HazardClass 8
PackingGroup II
HS Code 29349990
Storage Class8A - Combustible corrosive hazardous materials
Hazard ClassificationsEye Dam. 1
Met. Corr. 1
Skin Corr. 1B
MSDS Information
ProviderLanguage
Thiophene-2-carbonyl chloride English
SigmaAldrich English
ACROS English
ALFA English
2-Thiophenecarbonyl chloride Usage And Synthesis
Chemical PropertiesCLEAR COLOURLESS TO YELLOW-GREY LIQUID
Uses2-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.
Uses2-Thiophenecarbonyl chloride was used in the synthesis of building blocks derived from ornithine by undergoing acylation/sulphonation of copper complex of orthinine.
General DescriptionThe postfunctionalization reaction of 2-thiophenecarbonyl chloride with single walled carbon nanotubes (SWCNTs) was studied.
Synthesis
2-Acetylthiophene

88-15-3

2-Thiophenecarbonyl chloride

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
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