17361-89-6

Basic information

• Product Name: 5-PHENYL-2-THIOPHENECARBONYL CHLORIDE
• Synonyms: 5-Phenylthiophene-2-carbonyl chloride;2-(Chlorocarbonyl)-5-phenylthiophene, 2-(Chloroformyl)-5-phenylthiophene;5-PHENYL-2-THIOPHENECARBONYL CHLORIDE;BUTTPARK 98\04-17
• CAS NO: 17361-89-6
• Molecular Formula: C₁₁H₇ClOS
• Molecular Weight: 222.69
• Mol File: 17361-89-6.mol

Chemical Properties

• Boiling Point: 347.9 °C at 760 mmHg
• Flash Point: 164.2 °C
• Appearance: /
• Density: 1.305 g/cm³
• Vapor Pressure: 5.23E-05mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 5-PHENYL-2-THIOPHENECARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYL-2-THIOPHENECARBONYL CHLORIDE(17361-89-6)
• EPA Substance Registry System: 5-PHENYL-2-THIOPHENECARBONYL CHLORIDE(17361-89-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3261
• Hazardous Substances Data: 17361-89-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-PHENYL-2-THIOPHENECARBONYL CHLORIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its high reactivity allows for the formation of new chemical entities with potential therapeutic properties, contributing to the development of novel drugs for treating various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 5-PHENYL-2-THIOPHENECARBONYL CHLORIDE serves as a crucial building block for the creation of new agrochemicals. Its versatility in organic synthesis enables the production of innovative compounds with applications in crop protection, pest control, and other agricultural areas, enhancing crop yields and ensuring food security.
Used in Organic Synthesis:
5-PHENYL-2-THIOPHENECARBONYL CHLORIDE is utilized as a versatile reagent in organic synthesis processes. Its ability to undergo nucleophilic substitution reactions makes it an essential component in the preparation of a wide range of organic compounds, including fine chemicals, specialty chemicals, and other complex organic molecules.
Used in Research and Development:
In research and development settings, 5-PHENYL-2-THIOPHENECARBONYL CHLORIDE is employed as a valuable tool for exploring new chemical reactions and mechanisms. Its unique structure and reactivity provide opportunities for scientists to investigate novel synthetic pathways and develop innovative methodologies in organic chemistry.
Used in Chemical Education:
5-PHENYL-2-THIOPHENECARBONYL CHLORIDE can also be used as a teaching aid in chemical education. Its reactivity and involvement in various organic synthesis processes make it an excellent example for illustrating key concepts and techniques in organic chemistry, helping students to better understand the principles and applications of this field.

InChI:InChI=1/C11H7ClOS/c12-11(13)10-7-6-9(14-10)8-4-2-1-3-5-8/h1-7H

Upstream product

• 69202-28-4 2-(3-Oxo-prop-1-enyl-1-phenyl-1-thio)-acetanilid 
• 13781-37-8 2-iodo-5-phenylthiophene 
• 98-80-6 phenylboronic acid 
• 19163-21-4 5-phenylthiophene-2-carboxaldehyde 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 19163-24-7 5-phenyl-2-thiophenecarboxylic acid 

Downstream Products

• 333792-84-0 N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-5-phenyl-thiophene-2-carboxamide 
• 1025771-21-4 N-(2-chloro-5-((((1R)-1-phenylethyl)amino)methyl)-phenyl)-5-phenyl-2-thiophenecarboxamide 
• 190076-85-8 5-Phenyl-thiophene-2-carboxylic acid tert-butylamide 
• 62404-18-6 4-(5-phenyl-thiophene-2-carbonyl)-morpholine 
• 62404-17-5 N-(5-phenyl-2-thenoyl)piperidine 

Relevant articles and documents

Pine Rosin as a Valuable Natural Resource in the Synthesis of Fungicide Candidates for Controlling Fusarium oxysporum on Cucumber

To improve the effect of pine rosin in plant fungicides, four series of dehydroabietyl-1,3,4-thiadiazole derivatives from the natural product rosin were synthesized. Based on the evaluation of the in vitro antifungal activity against Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium oxysporum, and Magnaporthe oryzae, rosin-based 1,3,4-thiadiazole compounds containing thiophene heterocycles were screened. Notably, compound 3e [dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide] exhibited excellent antifungal property against F. oxysporum with an EC50 of 0.618 mg/L, which was lower than that of the positive control carbendazim (0.649 mg/L). The in vivo antifungal activity results showed that 3e exerted a protective effect on cucumber plants. Physiological and biochemical studies showed that the primary mechanism of action of compound 3e on F. oxysporum was it changed the mycelial morphology, increased the cell membrane permeability, and inhibited the synthesis of ergosterol in the mycelia. Furthermore, the quantitative structure-activity relationship studies revealed that the frontier orbital energy in the molecule had a key role in the antifungal activity through the conjugation and electrostatic interaction between compound 3e and the receptors of the target. Thus, the present study highlighted the application of rosin-based fungicidal candidates and exploited efficient plant pesticides for sustainable crop production.

Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection

In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on Valsa mali, Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium oxysporum. In vitro and in vivo antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on B. cinerea. In particular, compound 5b (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against B. cinerea with an EC50 of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound 5b on B. cinerea changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.

Amide compounds

The present invention is a compound and pharmaceutical composition comprising a compound of formula (I): wherein R1is a 4-(lower) alkyl-imidazol-1-yl or a 4,5-di(lower) alkyl-imidazol-1-yl group, R2is a hydrogen atom or a lower alkyl

Substituted hexahydrobenzo[f]thieno[c]quinolines as dopamine D1- selective agonists: Synthesis and biological evaluation in vitro and in vivo

A series of substituted 9,10- dihydroxyhexahydrobenzo[f]thieno[c]quinolines (TB[f]Q), varying with respect to the position of the thiophene relative to the benzo[f]quinoline core and the nature and position of the substituent on the thiophene, were prepared and evaluated for their affinity and selectivity for the dopamine D1-like receptor. The thieno[3,2-c]B[f]Q regioisomers bearing a small alkyl (C1-C3) substituent at the 2 position were potent (K(i) 50) D1 agonists with close to full agonist activity (IA > 85%). The compounds were resolved and found to exhibit a high level of enantiospecificity in their interaction with the D1 receptor. Selected compounds were tested in vivo in the 6-OHDA rodent model of Parkinson's disease and for their liability to produce seizure-like activities in mice. (5aR)-trans-2-Propyl-4,5,5a,6,7,11b-hexahydro-3-thia-5-azacyclopent-1- ena[c]phenanthrene-9,10-diol (5) emerged as the compound with the best overall in vivo profile in terms of potency (ED50 = 0.04 μmol/kg) and safety.