54863-47-7

Usage

Uses

Used in Pharmaceutical Industry:
11-Bromoundecyl cyanide, 12-Bromododecanenitrile, and 12-Bromolauronitrile are used as intermediates for the synthesis of N-(12-Aminododecyl)deoxynojirimycin (A608080), which is an imino-alditol and a glycosidase inhibitor. 11-Bromoundecyl cyanide, 12-Bromododecanenitrile, 12-Bromolauronitrile has potential applications in the treatment of various diseases, including cancer and viral infections, by inhibiting the activity of glycosidase enzymes.
Additionally, these compounds may have potential applications in other industries, such as the development of new materials or the synthesis of other specialty chemicals.

Upstream product

• 5048-44-2 11-dodecenenittrile 
• 73782-16-8 12-hydroxydodecanoic nitrile 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 1557201-27-0 potassium (11-bromoundecyl)trifluoroborate 
• 1557160-04-9 C₁₁H₂₄BBrO₂ 
• 7766-50-9 1-undecen-11-ylbromide 

Downstream Products

• 1365564-04-0 12-{2-[bis(3-phenylprop-2-ynyl)amino]phenoxy}dodecanenitrile 
• 1365564-03-9 12-{2-[bis(but-2-ynyl)amino]phenoxy}dodecanenitrile 

Relevant academic research and scientific papers

Direct wiring of cytochrome c's heme unit to an electrode: Electrochemical studies

A novel strategy for the immobilization of cytochrome c on the surface of chemically modified electrodes is demonstrated and used to investigate the protein's electron-transfer kinetics. Mixed monolayer films of alkanethiols and ω-terminated alkanethiols (terminated with pyridine, imidazole, or nitrile groups that are able to ligate with the heme) are used to adsorb cytochrome c to the surface of gold electrodes. The use of mixed films, as opposed to pure films, allows the concentration of adsorbed cytochrome to remain dilute and ensures a higher degree of homogeneity in their environment. The adsorbed protein is studied using electrochemical methods and scanning tunneling microscopy.

Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis

A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.

A mild, phosphine-free method for the conversion of alcohols into halides (Cl, Br, I) via the corresponding O-alkyl isoureas

A novel procedure for the conversion of primary and secondary alcohols into the corresponding alkyl chlorides, bromides and iodides is described. The transformation is high-yielding in the case of chlorides and bromides, tolerates a range of functional groups, and does not rely on the use of phosphines.

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).