2312-15-4

Basic information

• Product Name: 4-Dodecyloxybenzoic acid
• Synonyms: Benzoic acid, p-(dodecyloxy)-;para-Dodecyloxybenzoic acid;RARECHEM AL BE 0564;P-(DODECYLOXY)BENZOIC ACID;TIMTEC-BB SBB008006;4-DODECYLOXYBENZOIC ACID;4-N-DODECYLOXYBENZOIC ACID;4-n-Dodecyclobenzoic acid, 98%
• CAS NO: 2312-15-4
• Molecular Formula: C₁₉H₃₀O₃
• Molecular Weight: 306.44
• EINECS: 219-004-0
• Product Categories: 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: 2312-15-4.mol

Chemical Properties

• Melting Point: 132-137 °C
• Boiling Point: 407.04°C (rough estimate)
• Flash Point: 144.143 °C
• Appearance: White to light yellow crystal powder
• Density: 1.0139 (rough estimate)
• Vapor Pressure: 3.55E-08mmHg at 25°C
• Refractive Index: 1.5490 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.48±0.10(Predicted)
• Water Solubility: Insoluble in water. Soluble in N,N-Dimethylformamide.
• BRN: 2215914
• CAS DataBase Reference: 4-Dodecyloxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Dodecyloxybenzoic acid(2312-15-4)
• EPA Substance Registry System: 4-Dodecyloxybenzoic acid(2312-15-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2312-15-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemical Synthesis:
4-Dodecyloxybenzoic acid is used as an organic chemical synthesis intermediate for the production of various compounds and materials. Its versatile structure allows it to be a key component in the creation of pharmaceuticals, agrochemicals, dyes, and other specialty chemicals. The dodecyloxy group provides a hydrophobic character, which can be advantageous in the design and synthesis of target molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Dodecyloxybenzoic acid is used as a building block for the development of new drugs. Its chemical properties make it suitable for the synthesis of compounds with potential therapeutic applications, such as anti-inflammatory, analgesic, and antipyretic agents. The dodecyloxy group can also enhance the lipophilicity of the resulting drug molecules, potentially improving their bioavailability and efficacy.
Used in Agrochemical Industry:
4-Dodecyloxybenzoic acid is also utilized in the agrochemical industry for the synthesis of various pesticides and plant growth regulators. Its hydrophobic nature can be beneficial in formulating agrochemicals with improved stability, solubility, and target specificity, leading to enhanced crop protection and yield.
Used in Dye Industry:
In the dye industry, 4-Dodecyloxybenzoic acid is employed as an intermediate for the production of dyes with specific color properties and applications. Its chemical structure can be modified to create dyes for various substrates, such as textiles, plastics, and inks, offering a wide range of color options and performance characteristics.
Used in Cosmetics Industry:
4-Dodecyloxybenzoic acid can be used in the cosmetics industry for the development of skincare and personal care products. Its hydrophobic properties can be leveraged to create formulations with improved skin penetration, moisturization, and delivery of active ingredients, resulting in enhanced product performance and efficacy.

InChI:InChI=1/C19H30O3/c1-2-3-4-5-6-7-8-9-10-11-16-22-18-14-12-17(13-15-18)19(20)21/h12-15H,2-11,16H2,1H3,(H,20,21)

Upstream product

• 154845-75-7 ethyl 4-(dodecyloxy)benzoate 
• 143-15-7 1-dodecylbromide 
• 16782-08-4 sel de potassium de l'acide p-hydroxybenzoique 
• 99-96-7 4-hydroxy-benzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 112-52-7 1-chlorododecane 
• 40654-49-7 methyl 4-(dodecyloxy)benzoate 
• 4292-19-7 1-Iodododecane 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 112-53-8 1-dodecyl alcohol 
• 29147-92-0 4-(dodecyloxy)benzonitrile 
• 123-08-0 4-hydroxy-benzaldehyde 
• 24083-19-0 4-n-dodecyloxybenzaldehyde 

Downstream Products

• 50909-50-7 4-dodecyloxybenzoyl chloride 
• 70165-66-1 p-Dodecyloxy-α-methylstyrol 
• 137422-30-1 4-Dodecyloxy-benzoic acid 4-(2-nonanoyloxy-ethyl)-phenyl ester 
• 106316-09-0 4-dodecyloxy-3-chlorobenzoic acid 
• 56800-36-3 4-formylphenyl 4-(dodecyloxy)benzoate 
• 868620-29-5 4-(2`hydroxy-4`-dodecylhydroxybenzoylhydroxy)benzaldehyde 
• 2387-23-7 1,3-Dicyclohexylurea 

Relevant articles and documents

Synthesis and liquid crystalline properties of new triazine-based π-conjugated macromolecules with chiral side groups

In this study, we reported the synthesis of a new tribranched macromolecule liquid crystal with triazine in the centre. The central triazine core is bonded via sequences of Sonigashira coupling to 3 triazine unites through acetylenic bridges. The triazines at the periphery are substituted with 2 chiral citronellyloxy side groups. The salt of the resulting star-shaped macromolecule, which was oily at room temperature, with 4-dodecyloxybenzoic acid at 1:1 ratio exhibited a Smectic C (SmC) mesophase. The liquid crystalline properties of organic salt were investigated using DSC (differential scanning calorimetry) and POM (polarizing optical microscopy).

Acetylene-bridged triazine π-conjugated structures: Synthesis and liquid crystalline properties

We report the synthesis and liquid crystalline properties of a new type of tribranched compound built up from triazine as the central core and electron-rich triazine rings as peripheral groups. An equimolar mixture of the star-shaped compound based on the 1,3,5-triazine core with 4-dodecyloxybenzoic acid produced an organic salt exhibiting a columnar mesophase with a dendritic growing texture at low temperatures. The liquid crystalline properties of the triazine-based compound and organic salt were investigated by differential scanning calorimetry and polarizing optical microscopy.

Ionic interaction of tri-armed structure based on benzene ring: synthesis and characterization

Abstract: Liquid crystalline is a state of matter which combines the properties of liquid and a crystalline solid. Ionic liquid crystals are a new class of materials which exhibit phase transition at low temperature. A new structure was synthesized based on a benzene ring carrying three armed, two arms of triazine ring and the third arm is phenoxy benzene. The presence of alkyl chain groups on the periphery reduced the mesophase transitions which are desirable for low-temperature applications of liquid crystals. The substitution was achieved efficiently by Sonogashira coupling. The tri-armed compound was synthesized successfully through cross-coupling. However, it was oily and no transition phase was observed. Therefore, to increase the liquid crystal possibility, the compound was mixed with 4-(dodecyloxy)benzoic acid (4-DBA) with 1:1 ratio to produce an organic salt through hydrogen bonding. The organic salt obtained by ionic interaction between the tri-armed compound and 4-DBA exhibited a phase transition at low temperature. However, ionic liquid crystals are important class of mesomorphic materials and have considered as sealants due to their very low vapour pressure which demonstrated a proficient electrolyte systems for their anisotropic phase such as high ionic conductivity and diffusion along with excellent thermal stability. All the intermediate compounds and final compounds were confirmed by spectroscopic techniques (1H NMR, 13C NMR, FT-IR, and HRMS). Graphic abstract: [Figure not available: see fulltext.].

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 characterization of novel 4-benzyloxyphenyl 4-[4-(n-dodecyloxy) benzoyloxy]benzoate liquid crystal

Liquid crystal (LC) compound 4-Benzyloxyphenyl 4-[4-(n-dodecyloxy)benzoyloxy]benzoate (BDBB) was prepared and characterized. Inverse gas chromatography (IGC) was to be a beneficial analysis method for the research of thermodynamic characteristics of the new LC. Acetate and alcohol isomers were used to examine LC selectivity via the IGC technique at temperatures between 333.2 K and 483.2 K. The retention diagrams of n-heptane, n-octane, n-nonane, n-decane, undecane, dodecane, tridecane, n-butyl acetate, isobutyl acetate, ethyl acetate, n-propylbenzene, isopropylbenzene, ethylbenzene, chlorobenzene, and toluene on BDBB were plotted with temperatures of 483.2-493.2 K. Flory-Huggins interaction parameter and weight fraction activity coefficient at infinite dilution were researched for BDBB.

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.

Naphthoyl hydrazine organic gel factor as well as preparation method and application thereof

The invention relates to a naphthoyl hydrazine organic gel factor and a preparation method and application thereof. Where n is-18; wherein n is-18. The alkoxy benzoic acid and the condensation agent are mixed into a mixed solution, naphthalene carbonylhydrazide is added and the condensation reaction is carried out, and the alkoxy benzoic acid and the condensation agent are subjected to condensation reaction and can be prepared by separation and purification. The organic gel factor is mixed with an organic solvent, is heated and dissolved in a sealed state, and after cooling, an organic gel with fluorine ion responsiveness can be obtained. Compared with the prior art, the preparation method has the advantages of simple preparation process, mild reaction conditions, good gel ability for various organic solvents such as methanol and ethanol, and the like. The fluorinion has a remarkable specific response to fluoride ions in a gel state, and shows a remarkable advantage in the aspect of fluorine ion detection.

New macromolecular structures based on benzene core, synthesis and characterization

A series of new compounds based on benzene ring as a central core substituted with aromatic compounds such as (benzene and pyridine) and three armed of 2-chloro-4,6-bis((3,7-dimethyloct-6-en-1-yl) oxy)-1,3,5-triazine, have been obtained by sequential nucleophilic substitution of chlorine atoms in cyanuric chloride. The substitution at the acetylenic periphery on the central benzene ring has been achieved efficiently by Sonogashira coupling. Equimolar mixtures of the six-armed compounds based on the benzene core with the complementary 4-dodecyloxybenzoic acid, which already possessed liquid crystal property, has resulted in an organic salt. The obtained organic salts have been investigated by polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). The synthesized compounds have been confirmed by spectroscopic methods (1H and13C NMR and mass spectromery).

Synthesis and Characterization of New 1,3,5 -Triazine Derivatives Based on Benzene Ring

Liquid crystal materials have a number of ordinary uniqueness such as mechanical or electro-optical properties. New triazines derivatives compound was obtained starting from 1,3,5-triazine and 1,3,5-trichlorobenzene. The synthesized compound consists of three-armed, one arm of phenol and two armed of 2,4-bis-(dode-cyloxy)-6- ethynyltriazine that built up via reaction of triazine with dodecan-1-ol. The substitution was achieved efficiently at appropriate temperature under the argon atmosphere by cross coupling. However, the two armed of 2,4- bis(dodecyloxy)ethynyltriazine on the periphery are considered for liquid crystal application. The target compound did not exhibit a transition phase in its pure state but, after ionic interaction with 4-DBA which already possess a phase transition, it showed a phase transition and liquid crystal properties. We study the liquid crystal properties of obtained organic salts after ionic interaction through hydrogen bonding via methods of OPM "optical polarizing microscope"and DSC "differential calorimetric scanning). After purification with column chromatography then confirmed their structures by analysis of spectroscopy (MS, NMR, and FT-IR).

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.