16331-46-7

Usage

Uses

Used in Chemical Synthesis:
4-Ethoxybenzoyl chloride is used as an intermediate in the chemical synthesis of various organic compounds. It plays a crucial role in the production of pharmaceuticals, agrochemicals, and other specialty chemicals due to its versatile reactivity and functional group compatibility.
Used in Liquid Crystals Industry:
In the liquid crystals industry, 4-Ethoxybenzoyl chloride is used as an intermediate for the production of liquid crystal materials. These materials are essential components in the manufacturing of liquid crystal displays (LCDs), which are widely used in televisions, computer monitors, and other electronic devices. The compound contributes to the development of advanced liquid crystal formulations with improved performance characteristics, such as faster response times and better temperature stability.
Used in Research Studies:
4-Ethoxybenzoyl chloride may also be used in chemical synthesis studies, where it can serve as a valuable building block for the development of new compounds with potential applications in various fields, including pharmaceuticals, materials science, and environmental chemistry. Researchers can explore its reactivity and functional group compatibility to design and synthesize novel molecules with specific properties and functions.

InChI:InChI=1/C9H9ClO2/c1-2-12-8-5-3-7(4-6-8)9(10)11/h3-6H,2H2,1H3

Upstream product

• 619-86-3 4-(ethoxy)benzoic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 23676-09-7 ethyl 4-ethoxybenzoate 
• 16782-08-4 sel de potassium de l'acide p-hydroxybenzoique 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 23676-08-6 methyl 4-ethoxybenzoate 

Downstream Products

• 16830-82-3 4-ethoxy-thiobenzoic acid S-(2-morpholino-ethyl ester); hydrochloride 
• 67049-64-3 4-ethoxy-benzoic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 124143-21-1 (+/-)-4-ethoxy-benzoic acid-[trans-2-(4-phenyl-piperazino)-cyclohexyl ester]; hydrochloride 
• 67049-62-1 4-ethoxy-benzoic acid-(3-diethylamino-2,2-dimethyl-propylester); hydrochloride 
• 92727-03-2 4-ethoxy-benzoic acid-(2-isobutylamino-ethyl ester); hydrochloride 
• 78330-00-4 4-ethoxy-benzoic acid-(3-diethylamino-propyl ester) 
• 103159-92-8 17β-(4-ethoxy-benzoyloxy)-androst-4-en-3-one 
• 94267-66-0 N₂-(4-ethoxybenzoyl)thiosemicarbazide 
• 131589-99-6 4-ethoxy-benzoic acid-(2-diethylamino-ethylamide) 
• 92197-98-3 4-ethoxy-benzoic acid-(2-ethylamino-ethyl ester); hydrochloride 
• 101718-23-4 4-ethoxy-benzoic acid-(2,4,6-trimethyl-anilide) 
• 28099-20-9 1,4-Bicyclo<2,2,2>oktylen-di-p-aethoxybenzoat 
• 52568-53-3 2-(4-ethoxy-phenyl)-6,7-dihydro-5H-cyclopenta[d][1,3]thiazine-4-thione 

Relevant academic research and scientific papers

Synthesis and Study of Novel Mesogenic Homologous Series: 4-(4′- n -alkoxy benzoyloxy)- n -propyl Cinnamates

A novel homologous series of liquid crystals viz. 4-(4′-n-alkoxy benzoyloxy) n-propyl cinnamates comprising of 11 homologues has been synthesized. It is a middle ordered melting type of series with exhibition of smectic and nematic mesophases. The first to fifth members of the series are non-mesomorphic. Mesomorphic behavior commences from the sixth homologue. The octyloxy (C8) and decyloxy (C10) homologues are polymesomorphic. The smectic-nematic and nematic-isotropic transition curves behave in a normal manner except for the hexadecyl derivative, which slightly deviates from normal behavior (N-I). An odd-even effect was not observed for the N-I or Sm-N transition curves. The texture of nematic phase is threaded or Schlieren and that of the smectic phase is focal conic fan shaped of the smectic-A type. Transition temperatures and textures of mesophases were observed through an optical polarizing microscope equipped with a heating stage. Thermal stability and mesomorphic characteristics are compared with a structurally related series. Analytical and spectral data support the structure of the molecules.

Synthesis and study of liquid crystal properties of novel homologous series: α-4-[-4′-n-alkoxy benzoyloxy] phenyl β-4″-nitro benzoyl ethylenes

The synthesis and mesomorphic properties of a novel homologous series entitled α-4-[-4′-n-Alkoxy benzoyloxy] phenyl β-4 ″-nitro benzoyl ethylenes are reported. All the 11 members of the series except the methoxy and ethoxy derivatives are mesogenic. The propyloxy to pentyloxy and the hexadecyloxy homologues are only enantiotropically nematogenic and the rest of the mesogenic homologues are enantiotropically smectogenic in addition to nematogenic in character. A phase diagram shows the phase behavior through transition curves is of a normal type. An odd-even effect is observed for the nematic-isotropic transition curve. Analytical and spectral data support the molecular structure of the materials. Transition temperatures and other liquid crystal (LC) properties including average thermal stabilities for smectic and nematic were determined by optical polarizing microscopy. Average thermal stability for smectic and nematic are 125.6°C and 154.6°C, respectively. Smectogenic and nematogenic phase ranges vary between 19°C to 35°C and 14°C to 50°C, respectively. The LC properties of the novel series are compared with two other structurally similar homologous series. The textures of the nematic phase are threaded or schlieren type and those of the smectic phase is of the type A or C.

Mesomorphism and Molecular Structure of Ester Homologous Series Containing Carboxy and Vinyl Carboxy Linking Groups

A novel homologous series 4-(4′-n-alkoxy benzoyloxy)-isopentyl cinnamates consisting of eleven homologs is reported. Mesomorphism commences from the hexyloxy homolog up to the hexadecyloxy homolog. The hexyloxy and hexadecyloxy derivatives are only enantiotropically nematogenic while, but the octyl, decyl, dodecyl, and tetradecyl homologs exhibit enantiotropic nematogenic and smectogenic mesophases. The rest of the homologs are nonmesogenic. The textures of nematic phase are threaded or Schlieren and that of the smectic mesophase is focal conic smectic A or C type. The transition curves of the phase diagram behave in a normal manner without the exhibition of an odd-even effect. Analytical and spectral data confirm the molecular structure of the homologs. Overall mesogenic phase temperature range varies from 11.0°C to 59.0°C. The average thermal stabilities of smectic and nematic are 122.25°C and 139.0°C, respectively. The series is predominantly nematogenic and partly smectogenic with a middle-ordered melting type and a considerable range of liquid crystallinity. Melting points and transition temperatures were determined using an optical polarizing microscope equipped with a heating stage. The mesomorphic properties are compared with structurally similar series.

Synthesis and Mesomorphic Phase Behavior of Laterally Substituted Novel Azoesters

A novel homologous series of 4(4′-n-alkoxy benzoyloxy)phenylazo 2′′-chloro-3′′-methyl benzenes was synthesized and studied for mesophase behavior dependence on molecular structure. The nematogenic mesophase is exhibited from the first to the last member and the smectogenic mesophase from the hexyloxy to the tetradecyloxy member of the series. The nematic mesophase is of a threaded or Schlieren type, and the smectic mesophase is of a focal conic fan of the type A or C. Mesomorphic properties of the present novel homologous series are compared with other structurally similar homologous series.

Synthesis and characterization of new nematic liquid crystalline compounds-based thiophene units

Four new liquid crystalline thiophene compounds (M1-M4) with a long flexible spacer were prepared. Their structures were characterized by Fourier transform infrared and proton nuclear magnetic resonance. The mesomorphism and thermal stability were investigated with differential scanning calorimetry, polarizing optical microscopy, and thermogravimetric analysis. The photo-physical properties were evaluated using ultraviolet/visible spectroscopy and photoluminescence. M1-M4 all showed thermotropic mesogenic properties with excellent thermal stability, and exhibited nematic threaded texture, droplet texture, and Schlieren texture on heating and cooling cycles. The effect of flexible spacer and terminal groups on mesomorphic and spectroscopic property is discussed. The experimental results demonstrated that the tendency toward melting temperature (Tm) decreased, while isotropic temperature (Ti) increased with increasing the flexible spacer length. In CHCl3 solution, these thiophene compounds displayed an intense broad absorption band peaking within 230-340 nm and a maximum fluorescent emission wavelength at 426-439 nm.

Mesomorphic properties of chiral nematic star-shaped liquid crystals containing melitose as cores

Three star-shaped compounds (SSCs, c1-c3), are synthesized by using melitose as the chiral core and monacid (b1, b2 and b3) as side arms, respectively. The side arms (b1, b2 and b3), in which terminal chains are different, are introduced into the hydroxyl groups of melitose by esterification, respectively. The chemical structures of c1-c3 are confirmed by FT-IR and 1H NMR. The roles played by the chiral core and the side arms in the mesomorphic properties of the SSCs are studied. b1 is not a liquid crystal (LC), while b2 and b3 are nematic LCs. c1 is not a LC, while c2 and c3 are star-shaped LCs (SSLCs) and exhibit fingerprint texture of chiral nematic. c1, c2 and c3 are all levo-SSCs, which are different from their parent cores. The absolute value of their specific rotation increases with the increase of the terminal chain length of the side arms. The melting temperature of SSCs decreases with the increase of the terminal chain length of the side arms. For c2-c3, their mesomorphic region increases with the increase of the terminal chain length of the side arms. The results suggest that the LC properties of the side arms play an important role in inducing LC properties of the SSCs and the chiral core induces the chiral nematic of SSLCs, which contain the nematic LCs as the side arms.

Mesomorphism dependence on molecular rigidity

A novel ester homologous series of thermotropic liquid crystal (LC) has been studied with a view to understanding and establishing the relation between LC property and the molecular structure. The series consists of 11 members, the CCand Cmembers of the series are nonliquid crystals. LC properties commence from the Chomolog and continue up to the Chomolog as enantiotropic nematic and smectic in addition to nematic. Transition temperatures of the homologs were determined by an optical polarizing microscope equipped with a heating stage. Textures of nematic phase are threaded or Schlieren and that of smectic is focal conic of the type-A. Analytical and spectral data confirm the structures of homologs. Thermal stability for nematic is 93 °C and 136°C, respectively. The N-I and Sm-N transition curves of phase diagram do not exhibit odd-even effect. The N-I transition curve partly behaves in an abnormal manner. The Cr-I and Sm-N transition curves behave in normal manner. The LC behavior of the present series is compared with structurally similar known homologous series.

Ni-Catalyzed Direct Carboxylation of Aryl C?H Bonds in Benzamides with CO2

The direct carboxylation of inert aryl C?H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni-catalyzed direct carboxylation of aryl C?H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)?Ni(II)?Ni(I) catalytic cycle may be involved in this reaction. (Figure presented.).

Rh(iii)-Catalyzed three-component cascade annulation to produce theN-oxopropyl chain of isoquinolone derivatives

Developing powerful methods to introduce versatile functional groups at theN-substituents of isoquinolone scaffolds is still a great challenge. Herein, we report a novel three-component cascade annulation reaction to efficiently construct theN-oxopropyl chain of isoquinolone derivativesviarhodium(iii)-catalyzed C-H activation/cyclization/nucleophilic attack, with oxazoles used both as the directing group and potential functionalized reagents.

Design and synthesis of N-(3-sulfamoylphenyl)amides as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

The protozoan parasite Trypanosoma brucei (T. brucei) causes human African trypanosomiasis (HAT), which is a fatal and neglected disease in the tropic areas, and new treatments are urgently needed. Leucyl-tRNA synthetase (LeuRS) is an attractive target for the development of antimicrobial agents. In this work, starting from the hit compound thiourea ZCL539, we designed and synthesized a series of amides as effective T. brucei LeuRS (TbLeuRS) synthetic site inhibitors. The most potent compounds 74 and 91 showed IC50 of 0.24 and 0.25 μM, which were about 700-fold more potent than the starting hit compound. The structure-activity relationship was also discussed. These compounds provided a new scaffold and lead compounds for further development of antitrypanosomal agents.