54247-27-7

Usage

Uses

Used in Organic Synthesis:
BENZYL 6-BROMOHEXYL ETHER is used as a reagent for the formation of carbon-carbon bonds, which is crucial in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
It serves as an intermediate in the production of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Agrochemical Production:
BENZYL 6-BROMOHEXYL ETHER is also utilized as an intermediate in the creation of agrochemicals, playing a role in the synthesis of compounds used in agriculture to protect crops and enhance yields.
Used in the Production of Fine Chemicals:
BENZYL 6-BROMOHEXYL ETHER is employed in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, flavors, and specialty chemicals.

InChI:InChI=1/C13H19BrO/c14-10-6-1-2-7-11-15-12-13-8-4-3-5-9-13/h3-5,8-9H,1-2,6-7,10-12H2

Upstream product

• 71126-73-3 6-benzyloxyhexan-1-ol 
• 126519-80-0 6-benzyloxyhexyl 4-methylbenzenesulfonate 
• 629-03-8 1 ,6-dibromohexane 
• 100-51-6 benzyl alcohol 
• 4286-55-9 1-bromo-6-hexanol 
• 100-39-0 benzyl bromide 
• 55791-06-5 benzyl mesylate 
• 629-11-8 1,6-hexanediol 
• 1110667-74-7 O-6-(benzyloxy)hexyl dimethylcarbamothioate 

Downstream Products

• 91285-98-2 8-Benzyloxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-octanoic acid ethyl ester 
• 108296-25-9 2-(6-benzyloxyhexyl)isoindoline-1,3-dione 
• 108190-48-3 5-(6-Benzyloxy-hexyloxy)-6-methoxy-4-methyl-8-nitro-quinoline 
• 147566-01-6 7-(benzyloxy)heptanenitrile 
• 191412-48-3 8-Benzyloxy-2-methylene-octanoic acid ethyl ester 
• 188180-39-4 2-(16-benzyloxyhexadec-1-yl)bromide 
• 213542-10-0 9-(6-Benzyloxy-hexyl)-3-chloro-9H-fluoren-9-ol 
• 172668-88-1 (2S)-1-tert-Butyldimethylsilyloxy-2-methyl-9-benzyloxynonane 
• 946568-43-0 C₂₅H₄₁NO₆ 
• 124083-20-1 (R)-(+)-etomoxir 
• 191412-53-0 (S)-2-Bromomethyl-2,8-dihydroxy-octanoic acid 
• 191412-55-2 (S)-2-Bromomethyl-2,8-dihydroxy-octanoic acid methyl ester 
• 191412-56-3 (R)-2-(6-Hydroxy-hexyl)-oxirane-2-carboxylic acid ethyl ester 
• 191412-49-4 2-(6-benzyloxy)hexyl-2-en-propionic acid 

Relevant academic research and scientific papers

Stereoselective total synthesis of siladenoserinols A and D

The stereoselective total synthesis of siladenoserinols A and D has been accomplished using carbohydrate as a chiral template. The feature of this work is to build the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction of hydrogenation/deacetalization/ketalization in a one-pot process, that is, to take advantage of a thermodynamically controlled bicyclization of polyhydroxyketone under HCl/MeOH reaction conditions. The current cost-effective synthetic strategy could facilitate the bioactivity investigation of siladenoserinols.

Validating the 1,2-Difluoro Motif As a Hybrid Bioisostere of CF3and et Using Matrix Metalloproteinases As Structural Probes

Matrix metalloproteinases (MMPs) are involved in a spectrum of physiological processes, rendering them attractive targets for small-molecule drug discovery. Strategies to achieve selective inhibition continue to be intensively pursued, facilitated by advances in structural biology. Herein, we harness MMPs 2, 8, 9, and 13 to validate the vicinal difluoro motif as a hybrid bioisostere of CF3 and Et (BITE) in a series of modified barbiturate inhibitors. Crystallographic analyses of representative structures reveal conformations of the vicinal difluoro motif that manifest stabilizing hyperconjugative interactions consistent with the stereoelectronic gauche effect. Detailed docking studies of a potent difluorinated probe with MMP-9 are also disclosed and indicate that the structural basis of inhibition is a consequence of the anisotropic nature of the motif. Significant selectivity of MMP 13 versus MMP-2 can be achieved by subtle chain contraction in a BITE-modified inhibitor.

Preparation of Alkyl Ethers with Diallyltriazinedione-Type Alkylating Agents (ATTACKs-R) Under Acid Catalysis

Diallyltriazinedione-type acid-catalyzed alkylating agents (ATTACKs-R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium-catalyzed intramolecular O-to-N allylic rearrangement of 2,4-bis(allyloxy)-6-chloro-1,3,5-triazine was developed to introduce various alkoxy groups into the N,N′-dialkylated triazinedione skeleton. O-Alkylation of alcohols with ATTACKs-R was carried out in 1,4-dioxane in the presence of 2,6-di-tert-butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs-R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs-R bearing an o-nitro-substituted benzyl group tended to afford low yields. Comparison of four different triazinedione-based benzylating reagents suggested that the N,N′-substituents affected the reactivity.

Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues

The total synthesis of siladenoserinol A, an inhibitor of the p53–Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner–Wadsworth–Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53–Hdm2 interaction.

Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage

A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.

Cyclopropenone catalyzed substitution of alcohols with mesylate ion

The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.

Halogenation of primary alcohols using a tetraethylammonium halide/[Et 2NSF2]BF4 combination

The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et2NSF2]BF4 (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.

Primary alkyl bromides from dimethylthiocarbamates

The conversion of primary alkyl dimethylthiocarbamates into alkyl bromides using the Vilsmeier reagent occurs in high yields in the presence of other non-acid sensitive and non-nucleophilic functional groups. Georg Thieme Verlag Stuttgart · New York.

Benzylation of alcoholic hydroxyl groups with benzyl mesylate by using a catalytic amount of lithium tetrakis(pentafluorophenyl)borate in the coexistence of lithium triflate and magnesium oxide

Several alcohols possessing alkali-labile substituents such as halogen, ester and ketone were effectively benzylated with benzyl mesylate by using a catalytic amount of lithium tetrakis(pentafluorophenyl)borate [LiB(C6F5)4] in the coexistence of lithium triflate (LiOTf) and magnesium oxide (MgO) to afford the corresponding benzyl ethers in good to excellent yields.

Method of inhibiting parasitic activity

A method of inhibiting parasitic activity is disclosed in which the biosynthesis, structure and/or function of the glycosyl phosphatidylinositol (GPI) anchor of said parasite may be affected by incorporating into said GPI anchor selected analogs of myristic acid containing various heteroatoms, substituents and unsaturated bonds, including ester-containing analogs, ketocarbonyl-containing analogs, sulfur-containing analogs, double bond- and triple bond-containing analogs, aromatic moiety-containing analogs, nitrated analogs and halogenated analogs.