6742-54-7

Usage

Chemical Properties

liquid

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 2239, 1942 DOI: 10.1021/ja01262a001

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Vigorous reactions, sometimes amounting to explosions, can result from the contact with strong oxidizing agents. React exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. May attack some forms of plastics [USCG, 1999].

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: May attack some forms of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Stable; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

InChI:InChI=1/C17H28/c1-2-3-4-5-6-7-8-9-11-14-17-15-12-10-13-16-17/h10,12-13,15-16H,2-9,11,14H2,1H3

Upstream product

• 1002-69-3 decyl chloride 
• 108-88-3 toluene 
• 108-86-1 bromobenzene 
• 112-44-7 undecylaldehyde 
• 872-05-9 1-Decene 
• 693-67-4 bromoundecane 
• 108-90-7 chlorobenzene 
• 4282-44-4 1-iodo-n-undecane 
• 17746-05-3 undecanoyl chloride 
• 111-83-1 1-bromo-octane 
• 1462-75-5 3-phenylpropylmagnesium bromide 
• 111-85-3 n-chlorooctane 
• 626207-42-9 (3-phenylpropyl)zinc(II) bromide 
• 6990-68-7 1-phenylundecan-1-ol 

Downstream Products

• 96931-01-0 Aethyl-(p-n-undecylphenyl)-keton 
• 64357-59-1 2-Phenyl-1-(4-undecyl-phenyl)-ethanone 
• 958993-45-8 1-(4-undecylphenyl)ethanone 
• 39156-49-5 4-undecylbenzenesulfonic acid 
• 57736-32-0 4-undecylaniline 
• 1306630-55-6 C₅₄H₆₅N₅O₆ 
• 620180-55-4 C₂₃H₃₂N₂O 
• 64357-68-2 Phenyl-(4-undecyl-phenyl)-methanone 

Relevant academic research and scientific papers

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Relevance of Single-Transmetalated Resting States in Iron-Mediated Cross-Couplings: Unexpected Role of σ-Donating Additives

Control of the transmetalation degree of organoiron(II) species is a critical parameter in numerous Fe-catalyzed cross-couplings to ensure the success of the process. In this report, we however demonstrate that the selective formation of a monotransmetalated FeII species during the catalytic regime counterintuitively does not alone ensure an efficient suppression of the nucleophile homocoupling side reaction. It is conversely shown that a fine control of the transmetalation degree of the transient FeIII intermediates obtained after the activation of alkyl electrophiles by a single-electron transfer (SET), achievable using σ-donating additives, accounts for the selectivity of the cross-coupling pathway. This report shows for the first time that both coordination spheres of FeII resting states and FeIII short-lived intermediates must be efficiently tuned during the catalytic regime to ensure high coupling selectivities.

Synthesis of mesoporous ZSM-5 zeolites and catalytic cracking of ethanol and oleic acid into light olefins

Conversion of biomass-derived chemicals into light olefins is a promising method to maintain sustainable development of light olefin industry. In this study, three mesoporous ZSM-5 zeolites (MZSM-5-A, MZSM-5-B and MZSM-5-C) with major pore diameter about 4.8 nm, 16 nm and 22 nm were synthesized using a hydrothermal method by utilizing different templates. The catalytic activity of catalysts was studied by catalytic cracking of ethanol and oleic acid. The influence of reaction temperature on conversion and product selectivity was investigated. The characterization of ZSM-5 samples showed that the orders of the external surface area and mesopore volume were MZSM-5-C > MZSM-5-B > MZSM-5-A > conventional HZSM-5. In ethanol to light olefin reaction, MZSM-5-C achieved the highest light olefin yield (318.3 mL g?1) and ethylene selectivity (42.3%) at 400 °C. In oleic acid to light olefin reaction, MZSM-5-B achieved a complete conversion of oleic acid at 500 °C, and obtained the highest light olefin selectivity (38.1%) at 550 °C. The difference may be relevant to the size and chemical structure of feedstock molecular as well as the acidity of catalysts. Regardless of ethanol or oleic acid as feedstock, introduction of mesopore in zeolites significantly enhanced the light olefin yield and selectivity.

Nickel-Catalyzed Decarboxylative Alkylation of Aryl Iodides with Anhydrides

We present the anhydride-based decarboxylative alkylation of aryl iodides catalyzed by nickel. This method of decarboxylative coupling works with a broad scope of aliphatic carboxylic anhydrides and tolerates synthetically useful aromatic substituents. Assisted by a redox system of pyridine N-oxide and zinc additives, the current reaction occurs under mild conditions and without the assistance of photocatalyst. Notably, this method features high chemoselectivity toward alkyl migration with mixed aliphatic/aromatic anhydrides. Thus, it provides a powerful synthetic tool to modify high-valued aliphatic carboxylic acids by converting them into mixed anhydrides using readily available aryl carboxylic acids such as p-toluic acid. We propose a catalytic cycle that involves the key steps of free radical-based decarboxylation and subsequent alkyl transfer to nickel that precedes an oxidatively induced C-C reductive elimination from Ni(III).

NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)?H Alkylation of Alkenes

The terminal-selective, remote C(sp3)?H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3)?C(sp3) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.

Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes

The untraditional iron-catalyzed, ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel-Crafts reaction. HOMO-LUMO analysis and DFT studies on the key transition states underlying the regioselectivity are consistent with the observed reactions and the conclusions.

Efficient phosphine-mediated formal C(sp3)-C(sp3) coupling reactions of alkyl halides in batch and flow

The construction of C(sp3)-C(sp3) bond is an essential chemical transformation in synthetic chemistry due to its abundance in organic scaffolds. Here we demonstrate a valuable adaptation of the Wittig-type chemical procedure to efficiently facilitate C(sp3)-C(sp3) bond formation utilizing a range of alkyl building blocks. Additionally the method is amenable with flow synthesis to afford coupled products in good to excellent yields without laborious purification process.

Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents

A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.

Organometallic nickel(III) complexes relevant to cross-coupling and carbon-heteroatom bond formation reactions

Nickel complexes have been widely employed as catalysts in C-C and C-heteroatom bond formation reactions. In addition to Ni(0) and Ni(II) intermediates, several Ni-catalyzed reactions are proposed to also involve odd-electron Ni(I) and Ni(III) oxidation states. We report herein the isolation, structural and spectroscopic characterization, and organometallic reactivity of Ni(III) complexes containing aryl and alkyl ligands. These Ni(III) species undergo transmetalation and/or reductive elimination reactions to form new C-C or C-heteroatom bonds and are also competent catalysts for Kumada and Negishi cross-coupling reactions. Overall, these results provide strong evidence for the direct involvement of organometallic Ni(III) species in cross-coupling reactions and oxidatively induced C-heteroatom bond formation reactions.