14309-41-2

Basic information

• Product Name: octyl 4-aminobenzoate
• Synonyms: octyl 4-aminobenzoate;4-Aminobenzoic acid octyl ester
• CAS NO: 14309-41-2
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.3486
• Mol File: 14309-41-2.mol

Chemical Properties

• Boiling Point: 392.45°C (rough estimate)
• Flash Point: 226.3°C
• Appearance: /
• Density: 1.0065 (rough estimate)
• Vapor Pressure: 2.62E-06mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Water Solubility: 797.9ug/L(37 oC)
• CAS DataBase Reference: octyl 4-aminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: octyl 4-aminobenzoate(14309-41-2)
• EPA Substance Registry System: octyl 4-aminobenzoate(14309-41-2)

Safety Data

• Hazardous Substances Data: 14309-41-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H23NO2/c1-2-3-4-5-6-7-12-18-15(17)13-8-10-14(16)11-9-13/h8-11H,2-7,12,16H2,1H3

Upstream product

• 6500-50-1 n-octyl p-nitrobenzoate 
• 111-87-5 octanol 
• 122-04-3 4-nitro-benzoyl chloride 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 1250441-37-2 4-[4-hydroxy-3-(n-octyliminomethyl)phenylazo]benzoic acid octyl ester 
• 1250441-36-1 4-(3-formyl-4-hydroxyphenylazo)benzoic acid octyl ester 
• 1401709-86-1 C₁₅H₂₂INO₂ 
• 1415326-20-3 C₁₅H₂₁N₃O₂ 

Relevant articles and documents

Synthesis and cytotoxicity of some d-mannose click conjugates with aminobenzoic acid derivatives

Two sets of new conjugates obtained from d-mannose derivatives and o-, m-, and p-substituted benzoic acid esters interconnected through a triazole ring were synthesized by Cu(I) catalyzed azide-alkyne cycloaddition. All synthesized compounds were tested for their in vitro cytotoxic activity against seven cancer cell lines with/without multidrug resistance phenotype as well as non-tumor MRC-5 and BJ fibroblasts. Butyl ester of 4-aminobenzoic acid 6c showed the highest activity among all tested compounds, however, it was active only against K562 myeloid leukemia cells. N-Glycosyltriazole conjugates, both acetylated and nonacetylated at mannose moiety, were almost completely inactive. In contrast, some of the acetylated O-glycosyl conjugates showed cytotoxic activity which was cell line dependent and strongly affected by position of benzoic acid substitution as well as a length of its ester alkyl chain; the most potent compound was acetylated mannoside conjugated with octyl ester of m-substituted benzoic acid. However, deacetylation resulting in hydrophilicity increase of the glycosides almost completely abolished their cytotoxic potency.

Nickel(II) and palladium(II) complexes of azobenzene-containing ligands as dichroic dyes

A large series of complexes has been synthesized with two chelating, Schiff base azobenzene derivatives connected linearly by coordination to a central nickel(II) or palladium(II) ion. These compounds have the general formulas MII(OC6H3-2-CHNR-4-NdNC6H 4-4-CO2Et)2 [M = Ni; R = n-Bu (3c), n-C 6H13 (3d), n-C8H17 (3e), n-C 12H25 (3f), Ph (3g), OH (3h), C6H 4-4-CO2Et (3i). M = Pd; R = i-Pr (4a), t-Bu (4b), n-Bu (4c), n-C6H13 (4d), n-C8H17 (4e), n-C12H25 (4f), Ph (4g)], MII[OC 6H3-2-CHN(n-C8H17)-4-NdNC 6H4-4-CO2(n-C8H17)] 2 [M = Ni (9), Pd (10)], MII[OC6H 3-2-CHN(n-C8H17)-4-NdNC6H 4-4-C6H4-4-O(n-C7H 15)]2 [M = Ni (14), Pd (15)], and MII[OC 6H3-2-CHN(CMe2)-4-NdNC6H 4-4-CO2Et]2 [M = Ni (17), Pd (18); the CMe 2 groups are connected]. These compounds have been characterized by using various physical techniques including 1H NMR spectroscopy and matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. Single-crystal X-ray structures have been obtained for two pro-ligands and five complexes (3e, 4e, 14, 15, and 17). The latter always show a strictly square planar arrangement about the metal center, except for the NiII complex of a salen-like ligand (17). In solution, broadened 1H NMR signals indicate distortions from square planar geometry for the bis-chelate NiII complexes. Electronic absorption spectroscopy and ZINDO -S (Zerner's intermediate neglect of differential overlap) and TD-DFT (time-dependent density functional theory) calculations show that the lowest energy transition has metal-to-ligand charge-transfer character. The λmax of this band lies in the range of 409-434 nm in dichloromethane, and replacing NiII with PdII causes small blue-shifts. Dichroic ratios measured in various liquid crystal hosts show complexation-induced increases with NiII, but using PdII has a detrimental effect.

Smectogenic Salts Formed by Combination of Alkyl p-Aminobenzoates and p-Ethyl- or p-Chlorobenzenesulfonic Acid

Two series of smectogenic salts were obtained by combining alkyl p-aminobenzoates with p-ethyl- and p-chlorobenzenesulfonic acids, respectively.The shortest ester alkyl chain required to generate a smectic A phase is nonyl when the former sulfonic acid is employed but the chain may be as short as butyl when the latter is employed.The smectic A-isotropic transition temperature in the second series is significantly higher than that in the first series, indicating that the terminal substituent on the anion is as crucial as that in non-ionic mesogens in determining the mesophase stability. - Keywords: Smectic, alkyl p-aminobenzoates, benzenesulfonates