17687-72-8

Usage

Chemical Properties

Clear colorless to yellow liquid

InChI:InChI=1/C9H6BrNO/c10-7-1-2-8-6(5-12)4-11-9(8)3-7/h1-5,11H

Upstream product

• 17049-49-9 octylmagnesium bromide 
• 105-58-8 Diethyl carbonate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 3248-78-0 trioctylborane 
• 61949-23-3 menthyl formate 
• 111-66-0 oct-1-ene 
• 1421931-25-0 5,5-dimethyl-2-(9-octylheptadecan-9-yl)-1,3,2-dioxaborinane 
• 74-95-3 1,1-dibromomethane 
• 1421931-23-8 2-(9-octylheptadecan-9-yl)-1,3,2-dioxaborolane 
• 67-66-3 chloroform 

Downstream Products

• 24306-18-1 9-octylheptadec-8-ene 

Relevant academic research and scientific papers

Synthesis of deuterium-labelled polyoctylalkanes

The synthesis of specifically labelled 9-d-9-octylheptadecane (1) and 9-d-9,10-dioctyloctadecane (2) has been achieved using selective and specific deuterium labelling methods. The precursor to the latter compound, tetraoctyl ethene, has been achieved by a variant of the McMurry reaction which improves upon recently published methods.

Reactions between lithiated 1,3-dithiane oxides and trialkylboranes

Various 2-substituted-1,3-dithiane oxides (1-oxide and 1,3-dioxide) have been metalated and reacted for the first time with a trialkylborane (trioctylborane). The 2-chloro-1,3-dioxide results in migration of an octyl group from boron to carbon with the displacement of chloride and gives nonanoic acid after oxidation, but there is no evidence for a second migration involving displacement of a sulfenate group. The reaction involving lithiation of the 2-methoxy-1-oxide results in two migrations, with the displacement of both the methoxy group and the thiolate unit of the dithiane ring, giving dioctyl ketone after oxidation, but the yield is low, primarily because thiophilic addition of the lithiating agent predominates over lithiation. Again, there is no evidence for the displacement of the sulfenate unit. However, the intermediate prior to oxidation can be treated with trifluoroacetic anhydride to induce a Pummerer rearrangement, and the presumed trifluoroacetoxyalkylthiolate group then acts as a novel leaving group and is displaced, resulting in trioctylmethanol on oxidation, but the yield is again very low.

Reactions of organoboranes with carbanions bearing three potential leaving groups: unusual processes, products and mechanisms

Known reagents that transfer three alkyl groups of a trialkylborane intramolecularly to a single carbon atom lack features to influence stereochemistry. We have investigated four reagents of type LiCCl2X, where X might be amenable to variation. All behaved differently. With X=OR (R=cyclohexyl, menthyl), the reagent decomposed, leading to only low yields of triple migration products. With X=S(O)Ph, a single migration occurred, followed by isomerisation to boron enolate-like species that hydrolysed to α-chloroalkyl phenyl sulfoxides or reacted with aldehydes to aldol-like products. With X=SO2Ph, the major product was the corresponding α,α-dichloroalkyl phenyl sulfone, apparently formed through a redox reaction. With X=S(O)(NMe)Ph, products of three intramolecular alkyl migrations were obtained with unhindered trialkylboranes. Attempts have been made to gain understanding of the sulfoxide process by investigating proportions of aldol-like products, using X-ray crystallography and ab initio calculations.

Factors affecting reactions of trialkylcyanoborates with imidoyl chlorides/trifluoroacetic anhydride

Abstract Methods for generating tert-alkyl organoboron species are in high demand as they are invaluable intermediates for the synthesis of quaternary carbon centres. Herein we report investigations into generation of tert-alkyl organoboron species using imidoyl chlorides as reagents in the organoboron cyanidation reaction. Although alkenyl side-products predominate in particularly hindered cases, tert-alkyl organoboron species can be successfully generated for less hindered examples.

Factors affecting migration of tertiary alkyl groups in reactions of alkylboronic esters with bromomethyllithium

The reactions of bromomethyllithium with tert-alkylboronic esters could be of great potential for the formation of quaternary carbon centers but often give poor yields/conversions. Calculations and experimental evidence show that tert-alkyl groups migrate less effectively than other types of alkyl group in such reactions and that O-migration competes. Furthermore, slow/incomplete capture of the bromomethyl reagent by the boronic ester is a problem in more hindered systems, and an additional competing reaction, possibly Li-Br exchange on the bromomethylborate species, also leads to lower yields of migrated products. Based on this, experimental protocols have been devised in which the competing reactions are largely suppressed, leading to higher conversions to migrated product for several substrates.

Synthesis of symmetrical ketones from Grignard reagents and 1,1′-carbonyldiimidazole

Coupling reactions of 1,1′-carbonyldiimidazole with Grignard reagents provide a rapid and straightforward method for the synthesis of symmetrical ketones. Georg Thieme Verlag Stuttgart.

The First Phase-transfer catalysed Reactions of Trialkylboranes. A Highly Facile Synthesis of Trialkylmethanols from Alkenes

The phase-transfer catalysed reactions of trialkylboranes, generated in situ via hydroboration of alkenes, with chloroform and aqueous sodium hydroxide, followed by treatment with hydrogen peroxide, provide an economic and convenient metod for the synthesis of trialkylmethanols.