2493-84-7

Basic information

• Product Name: 4-N-OCTYLOXYBENZOIC ACID
• Synonyms: 4-OCTYLOXYBENZOIC ACID;4-N-OCTYLOXYBENZOIC ACID;LABOTEST-BB LT00114432;RARECHEM AL BO 0490;P-(OCTYLOXY)BENZOIC ACID;TIMTEC-BB SBB008044;4-n-Octyloxybenzoicacid,99%;PARA-N-OCTYLOXYBENZOICACID
• CAS NO: 2493-84-7
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Benzoic Acids (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Building block;Liquid Crystals;Organic Electronics and Photonics
• Mol File: 2493-84-7.mol

Chemical Properties

• Melting Point: 101-105 °C(lit.)
• Boiling Point: 353.47°C (rough estimate)
• Flash Point: 133.1 °C
• Appearance: White to light yellow crystal powder
• Density: 1.0589 (rough estimate)
• Vapor Pressure: 2.55E-06mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: almost transparency in hot Methanol
• PKA: 4.48±0.10(Predicted)
• CAS DataBase Reference: 4-N-OCTYLOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-OCTYLOXYBENZOIC ACID(2493-84-7)
• EPA Substance Registry System: 4-N-OCTYLOXYBENZOIC ACID(2493-84-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2493-84-7(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powder

General Description

White powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-N-OCTYLOXYBENZOIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 4-N-OCTYLOXYBENZOIC ACID to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Fire Hazard

Flash point data for 4-N-OCTYLOXYBENZOIC ACID are not available, however 4-N-OCTYLOXYBENZOIC ACID is probably combustible.

InChI:InChI=1/C15H22O3/c1-2-3-4-5-6-7-12-18-14-10-8-13(9-11-14)15(16)17/h8-11H,2-7,12H2,1H3,(H,16,17)

Upstream product

• 111-83-1 1-bromo-octane 
• 99-96-7 4-hydroxy-benzoic acid 
• 629-27-6 1-Iodooctane 
• 60-29-7 diethyl ether 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 24083-13-4 4-octyloxybenzaldehyde 
• 124-38-9 carbon dioxide 
• 96693-05-9 1-bromo-4-octyloxybenzene 
• 111-85-3 n-chlorooctane 
• 67-68-5 dimethyl sulfoxide 
• 111-87-5 octanol 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 72885-31-5 4-octyloxy-benzoic acid ethyl ester 

Downstream Products

• 129470-37-7 4-Octyloxy-benzoic acid 4-((R)-(S)-pentane-2-sulfinyl)-phenyl ester 
• 129470-36-6 4-Octyloxy-benzoic acid 4-((R)-(R)-pentane-2-sulfinyl)-phenyl ester 
• 103177-19-1 8-(p-octyloxybenzoyl)amino-2-(5-tetrazolyl)-4-oxo-4H-1-benzopyran 
• 137422-28-7 4-Octyloxy-benzoic acid 4-(2-nonanoyloxy-ethyl)-phenyl ester 
• 136260-12-3 C₄₉H₅₅N₃O₆ 
• 133675-94-2 4-Octyloxy-benzoic acid 4-((2S,4R)-4-butyl-5-oxo-tetrahydro-furan-2-ylmethoxy)-phenyl ester 
• 133675-93-1 4-Octyloxy-benzoic acid 4-((2S,4S)-4-butyl-5-oxo-tetrahydro-furan-2-ylmethoxy)-phenyl ester 
• 78352-93-9 C₅₂H₇₀O₈ 
• 92950-90-8 4-<(S)-2-methylbutoxy>phenyl 4-octyloxybenzoate 
• 103176-17-6 4-Octyloxy-N-[3-(1H-tetrazol-5-yl)-2,3-dihydro-benzo[1,4]dioxin-5-yl]-benzamide 
• 40782-53-4 4-octyloxybenzoic acid chloride 

Relevant articles and documents

The synthesis and dielectric properties of a new phenylbenzoate-based calamitic liquid crystal

The dielectric investigation has a great importance in liquid crystal studies as a supportive method to DSC for a complete characterization of liquid crystals as well as in the electronic applications. In this study, the synthesis, mesomorphic characterization and dielectric properties of a new phenylbenzoate-based three-ring calamitic liquid crystal which composed of ester linking groups, (S)-3,7-dimethyloctyloxy chiral unit at one of terminals and n-octyloxy chain at the other end of the molecule, have been reported. The new calamitic liquid crystal 4-[4-((S)-3,7-dimethyloctyloxy)phenoxy)carbonyl]phenyl 4-(n-octyloxy)benzoate (DPCPB) has been characterized using 1H, 13C-NMR and MS-QTOF. The liquid crystalline behavior of the target compound has been investigated by differential scanning calorimetry and optical polarizing microscopy. DPCPB exhibits an enantiotropic non-tilted smectic mesophase in a wide temperature range. The real and imaginary dielectric constant, conductivity mechanism, impedance and dielectric relaxation mechanism of DPCPB have been investigated depending on frequency at different temperatures.

Benzoate liquid crystals with direct isotropic-smectic transition and antipathogenic activity

A smectogen liquid crystal based on benzoate units has been synthesized and structurally characterized by FTIR and 1H NMR spectroscopy. Besides, its structure and supramolecular arrangement in the crystalline state was demonstrated by single cr

Synthesis and characterization of biphenyl-based azo liquid crystals and its optical properties: effect of lateral and tail group

An azo ester-based biphenyl substituted rod-shaped azo-based material has been synthesized and well-characterized and further studied their mesogenic, optical, and thermal properties. All the synthesized derivatives displayed enantiotropical nematic and SmC phases with good temperature range of mesophase which is further influence by the variation of alkyl chain. The present synthesized derivatives having left terminally substituted phenyl ring by -OR inbuilt with ester azo group and right terminally dodecyloxy tail (-OC12H25) at the right terminal end. The mesomorphism is measured by using POM, DSC, and high-temperature XRD technique, and the photophysical behavior was measured by UV-Vis spectroscopy.

Synthesis and mesomorphic characterization of some novel steroidal mesogens: A structure–property correlation

The steroidal derivatives are found to be extremely good mesogens since their inception. Because of their inherent chirality, they have the potential to induce a wide variety of liquid crystalline phases, including frustrated phases depending upon the structure of the steroidal skeleton and the substituents attached. In this report, a series of novel monoalkoxy and dialkoxy benzoate derivatives of ergosterol and a few monoalkoxy derivatives of stigmasterol have been synthesized and their mesomorphic property has been investigated. The derivatives exhibited various mesophases including SmA, SmC*, N*, TGB and blue phases. Also, the gelation ability of some of these derivatives with various organic solvents has been examined. Furthermore, the mesomorphism of these derivatives has been compared with the analogous cholesteryl counterparts.

Synthesis and mesomorphic properties of bis ester derivatives of coumarin containing chalcone linkage

Bis ester derivatives of coumarin containing chalcone linkage with various terminal alkoxy groups were designed, synthesized and characterized. Compounds 11a-m were studied for their mesomorphic properties using polarizing optical microscope & differential scanning calorimetry and photophysical properties using UV-vis & fluorescence spectroscopy. In this particular homologous series, compounds having lower flexible alkoxy chains showed very good mesogenic property with nematic mesophase formation, while analogues with higher chains failed to show any liquid crystalline property. Compound 11a with methoxy group showed very good absorbance and fluorescence as compared to higher chain length analogues.

Synthesis, mesomorphic properties and biological evolution of calamitic-shaped chalcone-based LCs: effect of lateral and terminal group

The mesomorphic properties of linear shaped homologous series based on two linkage group have been designed and synthesized with different side chain substituents (-OR) on the one end of terminal side with presence of lateral nitro group and second terminal iodo substituted group. Novel series consists thirteen members (C1 to C8, C10, C12, C14, C16, C18). Compounds (C1 to C6) showed nonliquid crystalline properties while compound (C7 to C18) displayed smectic and nematogenic mesophase properties. The textures of smectic C and nematic phase are fan, schlieren and droplets type. All these compounds were characterized by spectroscopic techniques such as [FTIR] and 1H Nuclear magnetic resonance [NMR] spectroscopy. The mesomorphic properties of these compounds were observed by POM and further confirmed by DSC and XRD. Chalconyl ester based compounds (C3 to C12) shows good antibacterial as well as antifungal activity compared with corresponding standard drugs.

λ-shaped to T-shaped azo diester mesogens having methyl (–CH3)/methoxy(–OCH3) terminal substituents with trisubstituted benzene

A two new homologous series of λ-shape to T-shape mesogenic azo diesters were synthesized, and their thermotropic properties were studied by differential scanning calorimetry and a hot-stage polarizing optical microscope. The difference between these two series is in the structure of terminal substituents methyl (–CH3) for series I and methoxy (–OCH3) for series II at one terminus. Structure variation from λ-shape to T-shape as we go from lower members to higher members is discussed. In the series I, methoxy to n-pentyloxy derivatives are non-mesogenic. n-hexyloxy derivative exhibits only monotropic nematic mesophase. n-heptyloxy to n-dodecyloxy derivatives exhibit monotropic smectic C mesophase. n-tetradecyloxy derivative exhibits enantiotropic SmA mesophase, whereas n-hexadecyloxy derivatives exhibit monotropic Smectic A mesophase. In series II, methoxy to n-hexyloxy derivatives are non-mesogenic. n-heptyloxy and n-octyloxy derivatives exhibit monotropic smectic C mesophase. Smectic A mesophase commences from the n-decyloxy derivative as a monotropic and persists up to the last member synthesized. The mesomorphic properties of the present series were compared with each other and with the structurally related mesogenic homologous series to evaluate the effect of methyl (–CH3)/methoxy (–OCH3) substituents as well as variation in the shape of the molecule by varying the alkoxy chain length of the bulky lateral substituent on mesomorphism.

Hydrogen bonding and the design of twist-bend nematogens

The phase properties of equimolar mixtures consisting of a hydrogen bond donor, a 4-alkoxybenzoic acid (nOBA), and one of two different stilbazole-based hydrogen bond acceptors, either 4-[(E)-2-(4-{[6-(4′-methoxy[1,1′-biphenyl]-4-yl)hexyl]oxy}phenyl)-ethenyl]-pyridine (1OB6OS) or 4-[(E)-4′-(6-{4-[(E)-2-(pyridin-4-yl)ethenyl]phenoxy}hexyl)-[1,1′-biphenyl]-4-carbonitrile (CB6OS) are reported. Neither hydrogen bond acceptor exhibits liquid crystal behaviour whereas the nOBA compounds show smectic and/or nematic behaviour depending on the length of the alkyloxy chain. For the complexes of an nOBA with n = 1–5, both conventional nematic and twist-bend nematic phases were observed, while for n ≥ 6 smectic phases emerged and the twist-bend nematic phase was extinguished. The CB6OS-nOBA mixtures may exhibit the heliconical smectic CTB phase. The local molecular arrangement in the two sets of mixtures are similar and changes on increasing n but this is not reflected in the nematic-isotropic transition temperatures. Birefringence studies of the mixtures are reported. In general the behaviour of the hydrogen-bonded mixtures is similar to that of their covalently bonded counterparts.

Coumarin substituted symmetric diaminopyridine molecules: Synthesis, mesomorphic characterizations and DFT studies

The 2, 6-diaminopyridine was symmetrically substituted with coumarins from a lateral side of the molecules. All the molecules characterized by standard spectroscopic methods such as infrared spectroscopy, and nuclear magnetic resonance spectroscopy techniques. Mesomorphic properties are evaluated by the differential scanning calorimetry and the polarized optical microscope. The measurements show that the lower members did not favour liquid crystal formation, while higher members are exhibiting liquid crystalline, namely Nematic mesophase. The DFT computations manifest the nature of liquid crystal geometrical aspects.

Synthesis and characterization of novel rod-like ester-based liquid crystalline homologous series: Effect of tert-butyl tail on mesomorphism

A new rod-like homologous series consisting twelve compounds with central ester linkage and terminal tert-butyl group, tert-butyl [4-(4’-n-alkoxybenzoyloxy)benzoates] has been synthesized and characterized through standard spectroscopic techniques like UV, FT-IR, 1HNMR, DSC, POM, and XRD. Methoxy and ethoxy derivatives are nonmesogenic. Nematic mesophase commences as enantiotropy from propyloxy derivative and persists up to the octadecyloxy derivatives. Smectic A mesophase commences as monotropy from propyloxy to the octadecyloxy derivatives. The mesomorphic properties of present series are compared with other structurally related series to evaluate the effect of terminal tert-butyl group on mesomorphism. Two derivatives are subjected to in?vitro antimicrobial activity.