3674-07-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Bromoacetic acid lauryl ester serves as a crucial intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Cosmetics and Personal Care Products:
As a surfactant, emulsifier, and wetting agent, 2-bromoacetic acid lauryl ester is utilized in the production of cosmetics and personal care products to improve their texture, stability, and effectiveness.
Used in Detergent Industry:
In the detergent industry, 2-bromoacetic acid lauryl ester enhances the cleaning power and foaming properties of detergents, making it an essential component in various cleaning formulations.
Used in Healthcare and Pharmaceutical Industries:
Leveraging its antimicrobial properties, 2-bromoacetic acid lauryl ester finds applications in healthcare and pharmaceuticals for sanitizing and preserving products, ensuring their safety and efficacy.
It is important to handle 2-bromoacetic acid lauryl ester with care due to its potential toxicity and harmful effects if ingested, inhaled, or absorbed through the skin.

InChI:InChI=1/C14H27BrO2/c1-2-3-4-5-6-7-8-9-10-11-12-17-14(16)13-15/h2-13H2,1H3

Upstream product

• 112-53-8 1-dodecyl alcohol 
• 598-21-0 2-Bromoacetyl bromide 
• 39695-18-6 ((dodecyloxy)methyl)benzene 
• 105-36-2 ethyl bromoacetate 
• 79-08-3 bromoacetic acid 

Downstream Products

• 22510-51-6 {2-[(4-Ethoxy-phenylaminooxalyl)-amino]-phenoxy}-acetic acid dodecyl ester 
• 1847-58-1 sodium lauryl sulphoacetate 
• 1310496-21-9 Br^(1-)*C₂₇H₃₉N₂O₄⁽¹⁺⁾ 
• 1539293-04-3 C₃₀H₃₆O₆ 

Relevant academic research and scientific papers

Synthesis, Characterization, and Surface Activities of Polymeric Cationic Thiol Surfactants in Aqueous Medium

A series of cationic polyurethane surfactants [PQ8-18] were synthesized by the reaction of alkyl bromoacetate (namely: octyl-, decyl-, dodecyl-, tetradecyl-, hexadecyl-, and octadecyl bromoacetate) as quaternizing agents and modified polyurethane contains tertiary amine species. Modified polyurethane was prepared by the reaction of toluene diisocyanate (TDI) and triethanol amine monomercaptoacetate. The chemical structures of the prepared surfactants were confirmed using elemental analysis, Fourier transform infrared spectroscopy (FTIR), and Proton nuclear magnetic resonance (1H NMR) spectroscopy. The molecular weight measurements of the prepared polymers showed that the segments of each polymer contain average 10 units of the urethane-triethanol amine mercaptoacetate. The surface activities of the prepared surfactants including: surface tension (γ), effectiveness (πcmc), concentration at micelle formation (CMC), efficiency (Pc20), maximum concentration at the interface (Γmax), and the average area occupied by each surfactant molecule at the interface at equilibrium (Amin) of surfactants solutions were established at 25°C. The surface tension and the critical micelle concentration values of the prepared surfactants were gradually decreased by the gradual increase of their alkyl chain length. The prepared cationic surfactants showed efficient activity as inhibitors for dissolution of carbon steel in an acidic medium and also as a biocide against the growth of bacteria, fungi, and yeast.

Surface and thermodynamic studies of N-((octyl, dodecyl, and cetyl) oxycarbonylmethyl) pyridinium bromide

N-Octyloxycarbonylmethyl pyridinium bromide (C8), N-dodecyloxycarbonylmethyl pyridinium bromide (C12) and N-cetyloxycarbonylmethyl pyridinium bromide (C16) were prepared. Several studies were carried out with their aqueous solutions. Surface tensions, electrical conductivities, and biodegradabilities were evaluated. The antibacterial and antifungal activities of the cationic surfactants were studied. Surface properties, particularly critical micelle concentration (CMC), effectiveness (ΠCMC), efficiency (Pc20), maximum surface excess (Γmax), and minimum surface area (Amin) were investigated at different concentrations at 20, 35, and 50°C respectively. Free energies, enthalpies, entropies of micellization, and adsorption of the surfactants in the aqueous solution were studied.

Structure and biological behaviors of some metallo cationic surfactants

In this study, different cationic surfactants were prepared by esterification with bromoacetic acid of different fatty alcohols, i.e., dodecyl, tetradecyl and hexadecyl species. The products were then reacted with diphenyl amine, and the resulting tertiary amines were quaternized with benzyl chloride to produce a series of quaternary ammonium salts. The metallocationic surfactants were prepared by complexing the cationic surfactants with nickel and copper chlorides. Surface tension of these surfactants were investigated at different temperatures. The surface parameters including critical micelle concentration (CMC), maximum surface excess (Γ max), minimum surface area (A min), efficiency (PC20) and effectiveness (π CMC) were studied. The thermodynamic parameters such as the free energy of micellization (δ Gmic°) and adsorption (δ Gads°), enthalpy (δ H m°), (δ Hads°) and entropy (δ Sm), (δ Sads°) were calculated. FTIR spectra and 1H-NMR spectra were obtained to confirm the compound structures and purity. In addition, the antimicrobial activities were determined via the inhibition zone diameter of the prepared compounds, which were measured against six strains of a representative group of microorganisms. The results indicate that these metallocationic surfactants exhibit good surface properties and good biological activity on a broad spectrum of microorganisms.

Screening for potential antimicrobial activities of some cationic uracil biocides against wide-spreading bacterial strains

Eight novel uracil-based cationic surfactants containing Schiff base species were synthesized and characterized using elemental analysis, FTIR, 1H-NMR and 13C-NMR spectroscopy. The surface activities of the synthesized Schiff bases and their cationic derivatives were determined based on interfacial tension measurements and partition coefficient values in water/octanol system. The synthesized Schiff bases and their cationic derivatives were evaluated as novel biocides against different bacteria and fungi strains. The results showed that the biocidal activity of the synthesized Schiff bases was considerably increased by quaternization. The influence of the cationic surfactants as biocides was increased by increasing the hydrophobic chain length and the presence of the methoxy groups. The biocidal activity was also increased by increasing the partition coefficient inwater/octanol system.The structure and surface activity/ biocidal activity of the different compounds were discussed. AOCS 2010.

Synthesis and in vitro transdermal penetration enhancing activity of lactam N-acetic acid esters

A homologous series of N-acetic acid esters of 2-pyrrolidinone and 2- piperidinone has been prepared and evaluated for its ability to enhance the skin content and flux of hydrocortisone 21-acetate in hairless mouse skin in vitro. Enhancement ratios (ER) were determined for flux (J), 24-hour diffusion cell receptor cell concentrations (Q24), and 24-h full-thickness mouse skin steroid content (SC) and compared to control values (no enhancer present). In addition, in an attempt to abrogate toxicity, these dermal penetration enhancers were designed to have the potential for biodegradation by dermal esterases. 2-Oxopyrrolidine-α-acetic acid dodecyl ester (5) showed the highest enhancement ratios for J (ER 67.33) and Q24 (ER 180.66). 2- Oxopiperidine-α-acetic acid decyl ester (10) showed a high Q24 (ER 162.07) but a lower J (ER 12.67). 2-Oxopyrrolidine-α-acetic acid decyl ester (3) showed the highest enhancement ratio for SC (ER 8.7). The ER Q24 for 3, 5 and 10, as well as other lactam N-acetic acid esters in this work, were significantly higher than the ER found using Azone as enhancer.

Synthesis of ester based cationic pyridinium gemini surfactants and appraisal of their surface active properties

New pyridinium gemini surfactants have been synthesized by esterification of halogenated carboxylic acids with long chain fatty alcohols furnishing respective esters (dodecyl-2-chloroacetate, tetradecyl-2-chloroacetate, hexadecyl-2-chloroacetate, dodecyl-2-bromoacetate, tetradecyl-2-bromoacetate and hexadecyl-2-bromoacetate) followed by their subsequent treatment with 4,4′-trimethylene dipyridine resulting in the formation of title Gemini surfactants: 4,4′-(propane-1,3-diyl)bis1-{2-(dodecyloxy)-2-oxoethyl}; 4,4′-(propane-1,3-diyl)bis{1-(2-(tetradecyloxy)-2-oxoethyl}; 4,4′-(propane-1,3-diyl)bis{1-(2-(hexadecyloxy)-2-oxoethyl} dipyridinium chlorides; 4,4′-(propane-1,3-diyl)bis{1-(2-(dodecyloxy)-2-oxoethyl}; 4,4′-(propane-1,3-diyl)bis{1-(2-(tetradecyloxy)-2-oxoethyl} and 4,4′-(propane-1,3-diyl)bis{1-(2-(hexadecyloxy)-2-oxoethyl} dipyridinium bromides. Their identifications are based on IR, 1H-NMR, 13C-NMR, DEPT, COSY and Mass spectral studies. Their surface active properties were also evaluated on the basis of surface tension and conductivity measurements.

Betaine ester-shell functionalized hyperbranched polymers for potential antimicrobial usage: Guest loading capability, pH controlled release and adjustable compatibility

Betaine ester-shell functionalized hyperbranched polyethylenimines (BEHPEI) were synthesized by Menschutkin reaction between per-N-methylated polyethylenimine (MeHPEI) and alkyl bromoacetate. BEHPEI could play dual antimicrobial roles that were, the betaine ester-shell acted as contact-based antibacterial polycations and the drug-loaded BEHPEI could controllably release the drugs due to the cleavage of the betaine ester groups under weak alkaline condition. The BEHPEI exhibited high transport capacities that per gram of BEHPEI could encapsulate 0.24-2.67 g of dyes or drugs. The model drug release experiment employing methyl orange (MO) showed that the drug release of MO-loaded BEHPEI complex occurred slowly in weak alkaline solutions and the release rate was controlled by varying pH, while the complex kept very stable under weak acid condition (pH = 3.0-7.0). BEHPEI generated from long chain alkyl bromoacetate was compatible with organic resins implying the possible usage in antimicrobial fibers and coatings. Another BEHPEI obtained from short-chain alkyl bromoacetate was water soluble and maybe used in lotion formula. The hydrolysis of BEHPEI afforded zwitterionic shell.

Surface charge-convertible quaternary ammonium salt-based micelles for in vivo infection therapy

Quaternary ammonium salts (QASs) are excellent candidates for treating stubborn bacterial infections caused by biofilms due to their high sterilization efficiency and potential inhibition of the development of drug resistance. However, the inherent toxicity of QASs, including cytotoxicity, protein absorption and hemolysis, severely limits their applications in vivo. Herein, a charge-convertible quaternary ammonium salt-based micelle (QAS-SL@CM) was constructed by co-assembly of two amphiphiles with opposite charges and shell cross-linking strategy. The toxicity of the QAS-SL@CM could be greatly reduced towards human cells contrast to the corresponding QASs. By response to the acidic environment at infection sites, the surface charge of QAS-SL@CM could be immediately changed to positive and then target to negatively charged bacteria. Furthermore, β-thiopropionate bonds on QAS-SL@CM could also be disintegrated under acid environment to release QASs to kill bacteria. Importantly, the QAS-SL@CM showed significant therapeutic effect in mice subcutaneous abscesses models without interference with normal cells. Therefore, a surface adaptive micelle constructed by charge-convertible strategy has been developed to overcome the cytotoxicity of QASs, and could intelligently respond to the microenvironment of infected wound for in vivo infection therapy, which shows promising application in clinic.

ARYLAZO-HETEROARYL COMPOUNDS AND THEIR USE FOR LONG-TERM THERMAL ENERGY STORAGE

The present invention relates to a compound of Formula (I): wherein R1, R2, m, n, p, Q, X, Y, W, and "A" are as described herein. The present invention also relates to a process for preparation of a compound of Formula (I). Also disclosed is a thermal-storage device comprising one or more compounds of Formula (I) and a method of storing energy.

Preparation method of tetra-ester gemini quaternary ammonium salt leather sterilization mildew inhibitor

The invention discloses a preparation method of a tetra-ester gemini quaternary ammonium salt leather sterilization mildew inhibitor. The preparation method comprises the following steps: firstly, taking hydroxyl-terminated diol and chloroacetyl chloride as reactants, and synthesizing ester dichloride through nucleophilic substitution reaction; then carrying out nucleophilic substitution reaction on the ester group dichloride and diethylamine to synthesize ester group di-tert-amine; then using fatty alcohol and bromoacetyl bromide as reactants to synthesize bromoacetate through acylation reaction; and finally, carrying out quaternization reaction on the obtained bromoacetate and ester group di-tert-amine to obtain the tetra-ester gemini quaternary ammonium salt bactericidal mildew inhibitor, and respectively distributing ester groups on a spacer group and a hydrophobic chain of the gemini quaternary ammonium salt. The tetra-ester gemini quaternary ammonium salt leather sterilization mildew inhibitor prepared by the method has good antibacterial and mildew-proof performance, can be applied to the sterilization and mildew-proof field of leather, and has a good market application prospect.