22809-37-6

Usage

Uses

Used in Organic Synthesis:
6-Bromohexanoyl chloride is used as a key intermediate for the synthesis of various organic compounds, facilitating the creation of a wide range of chemical products.
Used in Chemical Research:
As a versatile chemical intermediate, 6-Bromohexanoyl chloride is utilized in chemical research to explore new reactions, mechanisms, and the development of novel chemical entities.
Used in Agrochemicals:
6-Bromohexanoyl chloride is employed as a component in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Dye Industry:
In the dye industry, 6-Bromohexanoyl chloride is used as an intermediate for synthesizing various dyes, playing a crucial role in the production of colorants for different applications.

InChI:InChI=1/C6H10BrClO/c7-5-3-1-2-4-6(8)9/h1-5H2

Upstream product

• 4224-70-8 6-bromohexanoic acid 
• 34176-76-6 6-Bromhexansaeure-trimethylsilylester 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 2637-34-5 2-Sulfanylpyridine 
• 4509-90-4 5-bromovaleroyl chloride 
• 148116-22-7 1,5-Diazabicyclo[5.4.0]undec-5-ene 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 6621-59-6 6-bromo-1-hexanenitrile 

Downstream Products

• 73786-88-6 N-Dodecyl-N^α-(6-bromhexanoyl)-S-benzyl-L-cysteinamid 
• 71250-88-9 1-bromo-5-isocyanatopentane 
• 82777-11-5 6-bromo-1-phenyl-1-hexanone 
• 135980-31-3 N-(6-bromocaproyl)-N-(2-methoxybenzyl)amine 
• 151901-68-7 N-(toluene-p-sulfonyl)-3-(6-bromohexanoyl)pyrrole 
• 129090-53-5 6-Bromo-hexanoic acid pentakis-(6-bromo-hexanoyloxy)-phenyl ester 
• 129090-57-9 6-Bromo-hexanoic acid 2,3,4,5,6-pentakis-(6-bromo-hexanoyloxy)-cyclohexyl ester 
• 81877-54-5 4-(6-Bromo-hexanoyloxy)-benzoic acid 4-methoxy-phenyl ester 
• 78461-92-4 R-6-bromohexanoic acid N-α-methylbenzylamide 
• 129001-68-9 4-(benzyloxy)-3,5-bis(3-bromopropyl)-2',6'-bis(6-bromohexanamido)biphenyl 
• 83547-30-2 6-bromo-N-<6-methoxy-4-methyl-5-<3-(trifluoromethyl)phenoxy>-8-quinolinyl>hexanamide 
• 78222-59-0 N^α_asp-α_his-(6-bromohexanoyl)-N^im-tosyl-L-histidyl>-N-dodecyl-O-benzyl-L-aspartamide 
• 76152-22-2 N-dodecyl-Nα-(6-bromohexanoyl)-O-benzyl-L-aspartamide 
• 116058-82-3 N,N-ditetradecyl-Nα-6-bromohexanoyl-Nε-benzyloxycarbonyl-L-lysinamide 

Relevant academic research and scientific papers

Predictable adjustment of spin crossover temperature in solutions of iron(III) complexes functionalized with alkyl-urea tails

A new series of amphiphilic alkylurea functionalised iron(III) sal2trien complexes were prepared by substitution of phenolic ligand site with OCnH2n-NHC(=O)NHCmH2m+1 tails (n = 5, 9, m = 4, 12, 14, 16). These complexes display remarkably tunable spin-crossover (SCO) behaviour in solution. By imposing very slight structural modifications in the number of methylene recognition sites in a position remote from the functional unit, i.e. the SCO active iron(III) centre, the transition temperature T1/2 is modulated in a predictable manner. Additionally, a correlation between the concentration of the SCO-active amphiphile and its T1/2 allows for precise fine-tuning of the spin-transition properties and for quantifying the efficiency of self-assembly.

Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes

A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti-α-amino-β-hydroxy and α,β-dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.

A series of novel, potent, and selective histone deacetylase inhibitors

Histone deacetylase (HDAC) inhibitors offer a promising strategy for cancer therapy and the first generation HDAC inhibitors are currently in clinical trials. A structurally novel series of HDAC inhibitors based on the natural cyclic tetrapeptide Apicidin is described. Selected screening of the sample collection looking for L-2-amino-8-oxodecanoic acid (L-Aoda) derivatives identified a small acyclic lead molecule 1 with the unusual ketone zinc binding group. SAR studies around this lead resulted in optimization to potent, low molecular weight, selective, non-hydroxamic acid HDAC inhibitors, equipotent to current clinical candidates.

Radial control of recognition and redox processes with multivalent nanoparticle hosts

Mixed Monolayer Protected Gold Clusters (MMPCs) featuring both hydrogen bonding and aromatic stacking molecular recognition functionalities have been used to create multivalent hosts for flavins. Multitopic binding of these hosts to flavin was shown to have a strong radial dependence: when the recognition site was brought closer to the MMPC surface, recognition was enhanced ～3-fold due to increased preorganization. The effect of preorganization is reversed upon reduction of flavin, where the MMPC with longer side chains bind the flavin guest ～7-fold stronger than the short chain counterpart due to unfavorable dipolar interactions between the electron-rich aromatic stacking units of the host and the anionic flavin guest. This fine-tuning of recognition and redox processes provides both a model for enzymatic systems and a tool for the fabrication of devices.

Constitutional Dynamic Selection at Low Reynolds Number in a Triple Dynamic System: Covalent Dynamic Adaptation Driven by Double Supramolecular Self-Assembly

A triple dynamic complex system has been designed, implementing a dynamic covalent process coupled to two supramolecular self-assembly steps. To this end, two dynamic covalent libraries (DCLs), DCL-1 and DCL-2, have been established on the basis of dynamic covalent C-C/C-N organo-metathesis between two Knoevenagel derivatives and two imines. Each DCL contains a barbituric acid-based Knoevenagel constituent that may undergo a sequential double self-organization process involving first the formation of hydrogen-bonded hexameric supramolecular macrocycles that subsequently undergo stacking to generate a supramolecular polymer SP yielding a viscous gel state. Both DCLs display selective self-organization-driven amplification of the constituent that leads to the SP. Dissociation of the SP on heating causes reversible randomization of the constituent distributions of the DCLs as a function of temperature. Furthermore, diverse distribution patterns of DCL-2 were induced by modulation of temperature and solvent composition. The present dynamic systems display remarkable self-organization-driven constitutional adaption and tunable composition by coupling between dynamic covalent component selection and two-stage supramolecular organization. In more general terms, they reveal dynamic adaptation by component selection in low Reynolds number conditions of living systems where frictional effects dominate inertial behavior.

Lipophilic fluorescein probe and preparation method thereof

The invention relates to the field of lipophilic fluorescein probes, and particularly discloses a lipophilic fluorescein probe and a preparation method thereof. The lipophilic fluorescein probe according to the present application is represented by the following chemical formula 1, wherein R is a C1-C20 alkylene group or cycloalkylene group; and R' is C1-C20 alkyl, cycloalkyl, aralkyl, arcycloalkyl, alkaryl or naphthenic aryl. The lipophilic fluorescein probe is high in stability and not prone to self-hydrolysis, fluorescein can be released through rapid hydrolysis under the action of lipase, and therefore the lipophilic fluorescein probe has very high affinity acting force and very low detection limit on the lipase. In addition, the preparation method disclosed by the invention is simple to operate and high in yield .

Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study

Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable for optimizing modifications. Compared with gemfibrozil, compounds 7c and 15b were more potent activators of cGMP-forming activity of purified sGC and exhibited enhanced relaxation of preconstricted mouse thoracic aorta rings. These studies established the overall framework needed for futher improvement of sGC activators based on gemfibrozil scaffold.

Synthesis of N-trifluoromethyl amides from carboxylic acids

Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.

New desulfured troglitazone derivatives: Improved synthesis and biological evaluation

Breast cancer is a major medical threat which cannot be sufficiently addressed by current therapies because of spontaneous or acquired treatment resistance. Besides, triple-negative breast cancer (TNBC) tumors do not respond to targeted therapies, thus new therapeutic strategies are needed. In this context, we designed and prepared new desulfured troglitazone (TGZ)-derived molecules and evaluated them in vitro for their anti-proliferative activity, with a special focus on triple-negative breast cancer cell lines. Optimization of the synthetic strategies and deracemization of the lead compound were performed to give highly active compound 10 with low-micromolar potency. Further studies revealed that this compound triggers apoptosis rather than cell cycle arrest as observed with TGZ.

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.