6948-45-4

Usage

Uses

Used in Pharmaceutical Industry:
11-bromoundecanenitrile is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure, including the bromine atom and nitrile group, allows for the creation of a wide range of medicinal agents with diverse therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 11-bromoundecanenitrile is utilized as a precursor in the production of agrochemicals. Its reactivity and functional groups contribute to the development of effective pesticides, herbicides, and other agricultural chemicals that enhance crop protection and yield.
Used in Organic Synthesis:
11-bromoundecanenitrile is employed as a versatile reagent in organic synthesis. Its bromine atom facilitates halogenation reactions, while the nitrile group allows for various transformations, making it a valuable component in the synthesis of complex organic molecules for research and industrial applications.
Used in Chemical Research:
In the field of chemical research, 11-bromoundecanenitrile serves as a model compound for studying reaction mechanisms and exploring new synthetic methodologies. Its unique properties and reactivity provide insights into the development of innovative chemical processes and the understanding of fundamental organic chemistry principles.

Upstream product

• 5875-26-3 11-bromoundecanamide 
• 151-50-8 potassium cyanide 
• 4101-68-2 1,10-dibromodecane 
• 2834-05-1 11-bromoundecanoic acid 
• 15949-84-5 11-bromoundecanoyl chloride 
• 773837-37-9 sodium cyanide 
• 70326-40-8 11-bromoundecan-1-al 
• 85920-81-6 10-bromodecanal 

Downstream Products

• 102875-70-7 2,2-diphenyl-tridecanedinitrile 
• 4543-66-2 1,12-dodecanedinitrile 
• 102895-37-4 12-cyano-12,12-diphenyl-dodecanoic acid 
• 115291-64-0 2,2-diphenyl-tridecanedioic acid 
• 103100-69-2 2,2-diphenyl-tridecanedioic acid dimethyl ester 
• 78476-72-9 (10-Cyandecyl)triphenylphosphoniumiodid 
• 78476-73-0 3,5-Bis(11-cyan-1-undecenyl)veratrol 
• 78476-74-1 4,5-Dimethoxy-1,3-benzoldidodecannitril 
• 3732-26-1 Hydrochinon-bis-(10-cyan-decylaether) 

Relevant academic research and scientific papers

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

Electrical conductivity and glass formation in nitrile-functionalized pyrrolidinium bis(trifluoromethylsulfonyl)imide ionic liquids: Chain length and odd-even effects of the alkyl spacer between the pyrrolidinium ring and the nitrile group

The electrical conductivity of a series of pyrrolidinium bis(trifluoromethylsulfonyl)imide ionic liquids, functionalized with a nitrile (cyano) group at the end of an alkyl chain attached to the cation, was studied in the temperature range between 173 K and 393 K. The glass formation of the ionic liquids is influenced by the length of the alkyl spacer separating the nitrile function from the pyrrolidinium ring. The electrical conductivity and the viscosity do not show a monotonic dependence on the alkyl spacer length, but rather an odd-even effect. An explanation for this behavior is given, including the potential energy landscape picture for the glass transition. This journal is the Partner Organisations 2014.

Synthesis and biological evaluation of bivalent ligands for the cannabinoid 1 receptor

Dimerization or oligomerization of many G-protein-coupled receptors (GPCRs), including the cannabinoid 1 (CB1) receptor, is now widely accepted and may have significant implications for medications development targeting these receptor complexes. A library of bivalent ligands composed of two identical CB1 antagonist pharmacophores derived from SR141716 linked by spacers of various lengths were developed. The affinities of these bivalent ligands at CB1 and CB2 receptors were determined using radiolabeled binding assays. Their functional activities were measured using GTP-γ-S accumulation and intracellular calcium mobilization assays. The results suggest that the nature of the linker and its length are crucial factors for optimum interactions of these ligands at CB1 receptor binding sites. Finally, selected bivalent ligands (5d and 7b) were able to attenuate the antinociceptive effects of the cannabinoid agonist CP55,940 (21) in a rodent tail-flick assay. These novel compounds may serve as probes that will enable further characterization of CB1 receptor dimerization and oligomerization and its functional significance and may prove useful in the development of new therapeutic approaches to G-protein-coupled receptor mediated disorders.

Orthocarbonsaeure-ester mit 2,4,10-Trioxaadamantanstruktur als Carboxylschutzgruppe; Verwendung zur Synthese von substituierten Carbonsaeuren mit Hilfe von Grignard-Reagenzien

The surprising stability of 2,4,10-trioxa-3-adamantyl derivatives 1 against nucleophilic substitution by organomagnesium compounds is discussed and shown to be caused by unfavourable stereoelectronic and steric factors governing the substitution of these cage compounds (Scheme 2).As a consequence, a number of Grignard reagents 2 containing the carboxyl group masked as 2,4,10-trioxa-3-adamantyl group could be prepared and have been reacted in a second step with various electrophiles (cf.Scheme 4).In the products 7-13 and 15b the carboxyl masking group is removed by mild ac id hydrolysis and saponification (cf.Scheme 3) to yield the corresponding acids 16a-21a, 22, and 23a.Acids 21a and 23a have been further transformed to give the macrocyclic lactones 24 and 26, isolated from Galbanum oleo-gum-resin, and acid 22 to give 12-methyl-13-tridecanolide (25), isolated from Angelica root oil.In addition 1-bromo-ω-(2,4,10-trioxa-3-adamantyl)alkanes 1c and 1b have been used to synthesize (+/-)-methyl recifeiolate (29b) and pure cis-ambrettolic acid ((Z)-32a).