6271-23-4

Usage

Uses

Used in Organic Synthesis:
11-Bromoundecanoic acid ethyl ester is used as a reagent in organic synthesis for the production of pharmaceuticals and other fine chemicals. Its unique chemical structure allows for the creation of a variety of compounds, making it a valuable component in the synthesis process.
Used in Antifungal Applications:
Due to its fungicidal activity, 11-Bromoundecanoic acid ethyl ester is used as a potential antifungal agent. It can be employed in the development of antifungal products to combat fungal infections and protect various materials from fungal degradation.
Used in Flavor and Fragrance Industry:
11-Bromoundecanoic acid ethyl ester is used as a component in the manufacture of flavors and fragrances. Its unique properties contribute to the development of various scent profiles and enhance the sensory experience of consumer products.
Used in Surfactant and Emulsifier Production:
In the production of surfactants and emulsifiers, 11-Bromoundecanoic acid ethyl ester is utilized to improve the stability and performance of these compounds. Its incorporation aids in the formation of emulsions and the reduction of surface tension, making it an essential component in various industrial applications.
Used in Chemical Industry as an Intermediate:
11-Bromoundecanoic acid ethyl ester holds a significant position as an intermediate in the chemical industry. Its wide range of industrial applications and ability to be transformed into various other compounds make it a crucial component in the synthesis of numerous products.

InChI:InChI=1/C13H25BrO2/c1-2-16-13(15)11-9-7-5-3-4-6-8-10-12-14/h2-12H2,1H3

Upstream product

• 692-86-4 ethyl 10-undecenenoate 
• 2834-05-1 11-bromoundecanoic acid 
• 64-17-5 ethanol 
• 15949-84-5 11-bromoundecanoyl chloride 
• 112-38-9 10-undecenoic acid 
• 7664-93-9 sulfuric acid 
• 10035-10-6 hydrogen bromide 
• 3021-89-4 2-pentyl-2-nonenal 
• 71-43-2 benzene 
• 2041-15-8 1,3,5-cyclohexanetriol 

Downstream Products

• 103034-83-9 2-benzyl-tridecanedioic acid diethyl ester 
• 142504-47-0 ethyl 11-<4-(benzyloxycarbonyl)phenyloxy>undecanoate 
• 104273-57-6 11-(5-Benzoyl-1H-benzoimidazol-2-ylsulfanyl)-undecanoic acid ethyl ester 
• 102831-64-1 (ω-carbethoxyundecylidene)triphenylphosphonium bromide 
• 454686-11-4 11-p-tolyl-undecanoic acid ethyl ester 
• 7146-27-2 11-(2-Hydroxy-aethylmercapto)-undecansaeure 
• 121989-05-7 11-(4-nitro-phenoxy)-undecanoic acid 
• 108240-91-1 11-(4-methylphenyl)undecanoic acid 
• 454686-14-7 C₃₆H₅₄O₃ 
• 70794-53-5 <1-(ethoxycarbonyl)decyl>triphenylphosphonium iodide 
• 189025-37-4 11-(Triphenyl-λ⁵-phosphanylidene)-undecanoic acid ethyl ester 
• 7170-44-7 11-Phenoxyundecanoic acid 

Relevant academic research and scientific papers

Preparation and properties of a novel solution of hydrogen bromide (HBr) in 1,4-dioxane: An alternative reagent to HBr gas without protic solvents

A solution of hydrogen bromide (HBr) in 1,4-dioxane was prepared and investigated for its ability to brominate alcohols, and hydrobrominate alkenes. This study revealed that the brominating ability of this HBr/1,4-dioxane solution is equal or superior to that of hydrobromic acid or HBr in acetic acid. The solution of HBr in 1,4-dioxane is robust, exhibiting no decomposition of the solvent, and retaining 97% of its original concentration, when kept at ?25 °C for 30 days. This solution is a liquid alternative to HBr gas without protic solvents.

KuQuinones as sensitizers for NiO based p-type dye-sensitized solar cells

A new series of KuQuinones (KuQs) have been synthesized and employed as dye-sensitizers for NiO-based p-type dye-sensitized solar cells (p-DSSCs). KuQs are pentacyclic quinoid compounds which are characterized by a fully conjugated structure that is responsible for the strong and broad absorption in the visible spectrum. The HOMO/LUMO states of KuQs considered here have matching energy levels with the upper edge of the NiO valence band and I?/I3? redox potential energy. These features render such compounds suitable for NiO sensitization in p-DSSCs. The new carboxylic acid-substituted KuQ derivatives proposed here differ in the length of the alkyl chain. The JV characteristic curves and the external quantum efficiency spectra have been recorded. The results showed that the performances of KuQ-sensitized cells were similar to that of the benchmark sensitizer erythrosine B (Ery B), despite the lack of electronic conjugation between the anchoring group and the light absorbing unit. This result led us to hypothesize that the photoinduced charge transfer between the excited KuQ dyes and the NiO electrode occurred through space and not via chemical bonds as it usually occurs in these systems. The mechanism of charge transfer through space has been supported by data from IR spectroscopy.

Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50 of 9 μM and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GlyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 μM. This novel class of compounds show considerable promise as a first generation of GlyT2 transport inhibitors.

Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins

To improve access to a key synthetic intermediate we targeted a direct hydrobromination-Negishi route. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed. Re-examination of early reports revealed that selective Markovnikov addition, often simply termed "normal" addition, is not always observed with HBr unless air is excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol.

Efficient Syntheses of Star-Branched, Multifunctional Mesogens

Star-branched molecular architectures lend themselves to convergent synthesis strategies for creating materials that combine three or more functional modalities, but these approaches require a core moiety with several reactive groups that are orthogonal t

Antiproliferative and antimigratory actions of synthetic long chain n-3 monounsaturated fatty acids in breast cancer cells that overexpress cyclooxygenase-2

Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E2 (PGE2), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.

Ionic acylating agents for the enzymatic resolution of sec-alcohols in ionic liquids

Potential acylating agents containing pendant ionic groups have been screened for the enzymatic kinetic resolution of rac-secondary alcohols in ionic liquids with CAL-B as biocatalyst. This study has allowed the identification of the 1-methyl-3-alkylimidazolium cation attached to a carboxylate group through a C10-alkyl chain as an efficient acylating agent for this transformation. This strategy was applied to the resolution of 2-hydroxycyclohexanecarbonitrile in which the 1R,2S enantiomer was isolated in 35 % ee (73 % yield) and the 1S,2R enantiomer in 97 % ee (23 % yield). Potential acylating agents containing pendant ionic groups have been screened for the enzymatic kinetic resolution of rac-secondary alcohols in ionic liquids with CAL-B as biocatalyst. This study has allowed theidentification of the 1-methyl-3-alkylimidazolium cation attached to a carboxylate group through a C10-alkyl chain as an efficient acylating agent for this transformation. Copyright

Synthesis and characterization of o-hydroxybenzophenone chromophore bonded to aminopropyl silica gel microbeads

0-Hydroxybenzophenone (Hbp) chromophores were immobilized on 3-aminopropyl silica gel (SiO2-NH2) by a reaction of succinimidyl 4-(4-benzoyl-3-fiydroxyphenoxy)butanoate (2a) and -undecanoate (2b) with SiO2-NH2. t

Myosin light chain kinase inhibitor compounds, compostions and related methods of use

Pyridazinyl compounds, compositions and related methods of use.

One-pot enzymatic resolution and separation of sec-alcohols based on ionic acylating agents

(Figure Presented) Going their different ways: A simple, robust, efficient, and reusable system for the one-pot preparative resolution and separation of sec-alcohols is described. The system is based on the combination of sequential enzymatic kinetic resolution (lipase B from Candida Antarctica, CALB) and transesterification in ionic liquids (ILs) with an ionic acylating agent 1 and removal of each enantiomer by extraction with an organic solvent.