15949-84-5

Usage

Uses

Used in Surfactant Production:
11-bromoundecanoyl chloride is used as a key intermediate in the production of surfactants for its ability to enhance the properties of these compounds, such as solubility and emulsification capabilities, which are crucial in various industrial applications.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 11-bromoundecanoyl chloride serves as a critical component in the synthesis of various drugs. Its reactivity and functional groups make it suitable for creating new pharmaceutical agents with specific therapeutic properties.
Used in Agrochemical Production:
11-bromoundecanoyl chloride is utilized as a building block in the creation of agrochemicals, contributing to the development of effective pesticides, herbicides, and other agricultural products that are designed to improve crop yields and protect plants from pests.
Used in Protein and Peptide Modification:
For biological and medical applications, 11-bromoundecanoyl chloride is employed in the modification of proteins and peptides. This modification can alter the biological activity, stability, or targeting of these biomolecules, which is essential in research and therapeutic development.
Overall, 11-bromoundecanoyl chloride's widespread applications in the chemical industry highlight its importance in the synthesis of a diverse range of products across different sectors.

InChI:InChI=1/C11H20BrClO/c12-10-8-6-4-2-1-3-5-7-9-11(13)14/h1-10H2

Upstream product

• 2834-05-1 11-bromoundecanoic acid 
• 112-38-9 10-undecenoic acid 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 5875-26-3 11-bromoundecanamide 
• 87305-70-2 11-bromo-1-phenyl-1-undecanone 
• 41033-91-4 11-bromo-undecanoic acid phenyl ester 
• 73674-15-4 6,7,8,9,10,11,12,13,14,15-decahydro-4-methyl-2,3-benzo-1-thia-4-azacyclopentadecen-5-one 
• 148323-66-4 (4R,5S)-3-(11-Bromo-undecanoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 6271-23-4 11-bromoundecanoic acid ethyl ester 
• 78082-13-0 11-Bromo-undecanoic acid (2-{2-[(11-bromo-undecanoyl)-methyl-amino]-phenyldisulfanyl}-phenyl)-methyl-amide 
• 79898-79-6 11-bromoundecan-p-vinylanilide 
• 129090-60-4 11-Bromo-undecanoic acid 2,3,4,5,6-pentakis-(11-bromo-undecanoyloxy)-cyclohexyl ester 
• 73780-28-6 4-(11-Bromo-undecanoylamino)-benzoic acid ethyl ester 
• 87054-19-1 2-benzenethiol 
• 3732-20-5 11-Brom-undecansaeure-(2,5-diallyloxy-anilid) 
• 3732-18-1 1,4-Bis-(11-brom-undecanoyl-amino)-2,5-diethoxy-benzol 

Relevant academic research and scientific papers

Optically induced linking of protein and nanoparticles to gold surfaces

Attachment of molecules and proteins to surfaces is of great interest for the development of a large variety of applications. We present herein a novel approach to efficiently couple a molecule of choice to biological building blocks. We synthesized and employed a new derivative of 5-bromo-7-nitroindoline to attach nucleophilic molecules and proteins to gold surfaces by photochemical activation. The reaction can be seen as a photoactivated alternative to the activated ester type chemistries that are commonly used to attach proteins or molecules to surfaces. We characterize the reaction by UV-vis and NMR spectroscopy, and as test of principle experiment, we show that we can attach proteins to surfaces and demonstrate that we can functionalize gold nanoparticles by this optically induced cross-linking reaction.

Selective detection of non-aromatic pesticides via cyclodextrin-promoted fluorescence modulation

Reported herein is the detection of aliphatic pesticides using cyclodextrin-promoted fluorescence modulation. The introduction of the pesticide leads to noticeable changes in the emission of a fluorophore held in close proximity by cyclodextrin, leading to a pesticide detection system that operates with 100% successful differentiation and low limits of detection.

Fabrication of Gradient and Patterned Organic Thin Films by Bipolar Electrolytic Micelle Disruption Using Redox-Active Surfactants

Bipolar electrochemistry could be regarded as a powerful approach for selective surface modification due to the beneficial feature that a wirelessly controllable potential distribution on bipolar electrodes (BPEs). Herein we report a bipolar electrolytic micelle disruption (BEMD) system for the preparation of shaped organic films. A U-shaped bipolar electrolytic system with a sigmoidal potential gradient on the BPE gave gradient-thin films including various interesting organic compounds, such as a polymerizable monomer, an organic pigment and aggregation induced emission (AIE) molecules. The gradient feature was characterized by UV–Vis absorption, thickness measurements and surface morphology analysis. Corresponding patterned films were also fabricated using a cylindrical bipolar electrolytic setup that enables site-selective application of the potential on the BPE. Such a facile BEMD approach will open a long-term perspective with respect to organic film preparation.

Formation of organic thin films by electrolysis of surfactants with the ferrocenyl moiety

The formation of organic thin films by controlled-potential electrolysis (oxidation) of an aqueous solution containing surfactants with a ferrocenyl moiety and an organic compound incorporated in micelles or in a dispersed organic pigment with use of the surfactants is examined. Opaque films of five azo dyes, vinylcarbazole, cetyl alcohol, dioctadecyldimethylammonium chloride, and 4,4′-didodecylviologen are formed through the former mechanism. Transparent films of phthalocyanine compounds (MPc (M = H2, Cu)), four halogen derivatives of CuPc, three perylene derivatives, and two quinones are formed through the latter mechanism. The scanning electron micrograph studies show that crystal size of the film increases with electrolysis time in the case of the former mechanism and is the same for the added particles in the case of the latter mechanism. The adsorption isotherm of the surfactant on the pigment particle surface shows that they form monolayers at saturation and their desorption starts at slightly above the critical micelle concentration (cmc). These results suggest that the films formed through the former and the latter mechanisms are prepared by disruption of micelles and desorption of surfactant from the pigment surface, respectively.

Electrochromism of a bipolar reversible redox-active ferrocene-viologen linked ionic liquid

A ferrocene-viologen linked “bipolar” type redox-active ionic liquid ([FcC11VC1][TFSI]2) was synthesized as an electrochromic (EC) material that functions without any other additives: solvents, supporting electrolytes and sacrificial agents. The efficiency of a prototype symmetrical EC cell was 70 cm2 C?1 at 1.0 V. The EC process was stable even after over 10?000 potential cycles.

Synthesis of [1]benzothieno[3,2-b][1]benzothiophene pendant and norbornene random co-polymers via ring opening metathesis

2-Octyl-7-(11-(cis-5-norbornene-endo-2,3-dicarboxylicimide)undecane)[1] benzothienopheno[3,2-b] benzothienophene (1) was synthesised and co-polymerised with varying amounts of 1-decyl(cis-5-norbornene-endo-2,3-dicarboxylic) imide (2) or norbornene, using a ruthenium catalyst, to produce a series of random co-polymers.

Supramolecular assemblies formed by new L-lysine derivatives of viologens?

L-Lysine derivatives of viologens form supramolecular assemblies of fibers and ribbons in some aromatic solvents, and the charge separation reaction in these self-assembling systems proceeds with a similar efficiency to the MV2+ system.

Self-assembly of pyridinium-functionalized anthracenes: Molecular-skeleton-directed formation of microsheets and microtubes

Two amphiphilic regioisomers, 9-AP (1-[11-(9-anthracenylmethoxy)-11- oxoundecyl]pyridinium bromide), and 2-AP (1-[11-(2-anthracenyl methoxy)-11-oxoundecyl]pyridinium bromide), were synthesized and their assembly behaviors were studied. Due to the anisotropic features of the anthracene structure, different substituted positions on the anthracene ring lead 9-AP and 2-AP to adapt "shaver" and "spatula"-like molecular shapes, respectively, which consequently dictate the structure of their final assemblies. While "shaver"-shaped 9-AP assembled into microsheets, driven by π-π interactions, "spatula"-shaped 2-AP assembled into microtubular structures, promoted primarily by charge-transfer interactions. Self-assembly: Two anthracene-based amphiphilic regioisomers, 9-AP and 2-AP, were synthesized. Due to the anisotropy of the anthracene structure, different substitutions on anthracene rings led 9-AP and 2-AP to adapt different molecular structures and self-assembled morphologies (see figure). While "shaver"-shaped 9-AP assembled into microsheets through π-π interactions, "spatula"-shaped 2-AP transformed into microtubes due to charge-transfer interactions.

DNA-binding and photocleavage properties of cationic porphyrin-anthraquinone hybrids with different lengths of links

Four cationic porphyrin-anthraquinone (Por-AQ) hybrids differing in lengths of flexible alkyl linkage, 5-[4-(1-N-anthraquinonon-yl)-l-oxophenyl]-10,15,20-tris(N-methylpyridinium-4-yl)porphyrin triiodide, (l = acetyl, pentanoyl, octanoyl, undecanoyl, designed as [AQATMPyP]I3, [AQPTMPyP]I3, [AQOTMPyP]I3 and [AQUTMPyP]I3, respectively, see Fig. 1), were synthesized and their interactions with DNA were investigated. The results of spectroscopic, denaturation and viscosity measurements suggest that [AQATMPyP]I3 binds to DNA through non-intercalative mode while the other three hybrids with longer links bind via bis-intercalative mode. Ethidium bromide (EB) competition experiment was carried out to determine the binding constants (Kb) of these compounds for CT DNA, and [AQPTMPyP]I3 shows the largest Kb among these hybrids. The photocleavage mechanism and wavelength-dependent cleaving abilities of these hybrids to pBR322 plasmid DNA were also comparably investigated.

Development of pyrene-based fluorescent ether lipid as inhibitor of SK3 ion channels

We report the synthesis of three bioactive pyrene-based fluorescent analogues of Ohmline which is the most efficient and selective inhibitor of SK3 ion channel. The interaction of these Ohmline-pyrene (OP1-3) with liposomes of different composition reveals that only OP2 and OP3 are readily integrated into liposomes. Fluorescence measurements indicate that, depending on their concentration, OP2 and OP3 exist either as monomer or as a mixture of monomer and excimers within the liposome bilayer. Among the three Ohmline Pyrene compounds (OP1-3) only OP2 is able to reduce SK3 currents and is the first efficient fluorescent modulator of SK3 channel as revealed by patch clamp measurements (- 71.3 ± 13.3% at 10 μM) and by its inhibition of SK3-dependent cancer cell migration at (?32.5% ± 4.8% at 1 μM). We also report the first fluorescence study on living breast cancer cells (MDA-MB-231) showing that OP2 is rapidly integrated in bio-membranes followed by cell internalization.