693-67-4

Usage

Uses

1. Used in Organic Synthesis:
1-Bromoundecane is used as a reagent for the preparation of Grignard reagents by reacting with magnesium (Mg) in tetrahydrofuran (THF). This application is crucial in organic synthesis, as Grignard reagents are versatile tools for the formation of carbon-carbon bonds and the synthesis of various organic compounds.
2. Used in Pharmaceutical Industry:
1-Bromoundecane serves as an important raw material and intermediate in the pharmaceutical industry. Its unique chemical properties make it a valuable component in the development of new drugs and medications.
3. Used in Dye Industry:
In the dye industry, 1-Bromoundecane is utilized as a key intermediate for the synthesis of various dyes. Its chemical structure allows for the creation of a wide range of colored compounds, which are essential for various applications, including textiles, plastics, and printing inks.
4. Used in Agrochemicals:
1-Bromoundecane is also employed in the agrochemical industry as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its role in this industry is vital for the development of effective and environmentally friendly solutions for crop protection and management.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 2550, 1980 DOI: 10.1021/jo01300a071

InChI:InChI=1/C11H23Br/c1-2-3-4-5-6-7-8-9-10-11-12/h2-11H2,1H3

Upstream product

• 112-42-5 undecyl alcohol 
• 821-95-4 1-undecene 
• 143-07-7 lauric acid 
• 66605-81-0 11-Bromoundecyl tosylate 
• 103227-45-8 2-bromohexanoyl dodecanoyl peroxide 
• 55101-35-4 undecanyl radical 
• 105-36-2 ethyl bromoacetate 
• 83486-02-6 C₁₇H₂₈Br₂Te 
• 148773-54-0 1-bromo-11-(phenylthio)undecane 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 18268-45-6 silver laurate 
• 60-29-7 diethyl ether 
• 67-66-3 chloroform 

Downstream Products

• 78906-84-0 1-undecyl-pyridinium; bromide 
• 71899-44-0 octadec-6-yne 
• 112-42-5 undecyl alcohol 
• 26186-02-7 tridec-1-yne 
• 629-97-0 n-docosane 
• 5332-52-5 Undecane-1-thiol 
• 112-44-7 undecylaldehyde 
• 109647-44-1 4-ethoxycarbonyl-1-methyl-1-undecyl-piperazinium; bromide 
• 335457-78-8 1,2-diundecyloxybenzene 
• 116296-31-2 2-(undecylthio)acetic acid 
• 33584-24-6 N-undecylaniline 
• 80538-84-7 4-n-undecyloxyphenol 
• 857579-51-2 1,4-bis(undecyloxy)benzene 
• 46997-98-2 N-methyl-N-undecylaniline 

Relevant academic research and scientific papers

Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes

A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.

Method for decarboxylation and in-situ methylation of alkyl active carboxylic ester

The invention relates to a method for decarboxylation and in-situ methylation of alkyl active carboxylic ester. The method comprises the following step: in the presence of a cobalt catalyst, a phosphine ligand and an organic solvent, reacting alkyl active carboxylic ester with a trimethyl aluminum reagent to obtain a target methylated product. According to the provided method, trimethyl aluminum is used as a methylation reagent, so that a series of important secondary carbon and tertiary carbon centers are commercially and conveniently constructed successfully; the used carboxylate substrate is rich in source and simple to synthesize; compared with a traditional synthesis method reported before, the method avoids the use of a noble metal catalyst, and meets the requirements of green environment-friendly chemistry; the functional group compatibility is wide, the method is successfully applied to gram-scale reaction, the conversion rate is high, and the method has an important syntheticchemical value.

Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents

A cobalt-catalyzed decarboxylative methylation of aliphatic redox-active esters [ N-(acyloxy)phthalimides; RAEs] with trimethylaluminum under mild conditions was developed, providing a method for transforming a carboxylate group into a methyl group without redox fluctuation. Primary and secondary RAEs were both amenable substrates, whereas a tertiary RAE delivered an elimination product. Triethylaluminum was also used to deliver a decarboxylative ethylation product.

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES

The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Copper-catalyzed reduction of alkyl triflates and iodides: An efficient method for the deoxygenation of primary and secondary alcohols

We describe an effective method for catalytic reduction of 1°alkyl sulfonates, and 1°and 2°iodides in the presence of a wide range of functional groups. This Cu-catalyzed reaction provides a means for the effective deoxygenation of alcohols, as demonstrated by the highly selective reduction of 1°alcohols using a triflation/reduction sequence. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Primarily reduced: The copper-catalyzed reduction of 1°alkyl sulfonates, and 1°and 2°iodides, which is effective in the presence of a wide range of functional groups, provides a means for the effective deoxygenation of alcohols. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Copyright

NHC-copper hydrides as chemoselective reducing agents: Catalytic reduction of alkynes, alkyl triflates, and alkyl halides

The NHC-copper-catalyzed Z-selective semi-reduction of terminal and internal alkynes, as well as the NHC-copper-catalyzed reduction of primary alkyl triflates and primary and secondary alkyl iodides and bromides are described. The high chemoselectivity demonstrated in these examples illustrates the mild nature of copper hydride complexes as reducing agents, which have applications in synthetic chemistry beyond their traditional role in the reduction of activated alkenes and carbonyl compounds.

Rhodium-catalyzed tandem isomerization/hydroformylation of the bio-sourced 10-undecenenitrile: Selective and productive catalysts for production of polyamide-12 precursor

The hydroformylation of 10-undecenenitrile (1) - a substrate readily prepared from renewable castor oil - in the presence of rhodium-phosphane catalysts systems is reported. The corresponding linear aldehyde (2) can be prepared in high yields and regioselectivities with a (dicarbonyl)rhodium acetoacetonate-biphephos [Rh(acac)(CO)2-biphephos] catalyst. The hydroformylation process is accompanied by isomerization of 1 into internal isomers of undecenenitrile (1-int); yet, it is shown that the Rh-biphephos catalyst effectively isomerizes back 1-int into 1, eventually allowing high conversions of 1/1-int into 2. Recycling of the catalyst by vacuum distillation under a controlled atmosphere was demonstrated over 4-5 runs, leading to high productivities up to 230,000 mol (2)×mol (Rh)-1 and 5,750 mol (2)×mol (biphephos)-1. Attempted recycling of the catalyst using a thermomorphic multicomponent solvent (TMS) phase-separation procedure proved ineffective because the final product 2 and the Rh-biphephos catalyst were always found in the same polar phase. Auto-oxidation of the linear aldehyde 2 into the fatty 10-cyano-2-methyldecanoic acid (5) proceeds readily upon exposure to air at room temperature, opening a new effective entry toward polyamide-12. Copyright

Synthesis of [14C] acids from their unlabeled counterparts and application toward a novel [14C] labeled hepatitis C virus polymerase inhibitor

A strategy has been developed for the rapid construction of a [ 14C] acid from either an aromatic or an alkyl acid via a decarboxylation-carboxylation sequence. A [14C] labeled heptatitis C virus polymerase inhibitor was prepared. Other examples and the limitations of this methodology are discussed. Copyright

A photoirradiative phase-vanishing method: Efficient generation of HBr from alkanes and molecular bromine and its use for subsequent radical addition to terminal alkenes

A triphasic phase-vanishing (PV) system comprised of an alkane, perfluorohexanes, and bromine was successfully combined by photoirradiation to efficiently generate hydrogen bromide, which underwent radical addition with 1-alkenes in the hydrocarbon layer to afford terminal bromides in high yields. Georg Thieme Verlag Stuttgart.