1595-16-0

Usage

Chemical family

Alkylbenzenes

Structure

Benzene ring with a methyl group at position 1 and a 1-methylpropyl group at position 4

Primary use

Fragrance ingredient in perfumes and scented products

Odor description

Sweet, floral, woody, warm, and slightly spicy

Industrial application

Solvent in various processes

Popularity in the fragrance industry

Widely used in perfumes, colognes, and other scented products due to its pleasant aroma and versatile properties

InChI:InChI=1/C11H16/c1-4-10(3)11-7-5-9(2)6-8-11/h5-8,10H,4H2,1-3H3

Upstream product

• 81676-11-1 α,β,p-trimethylstyrene 
• 108-88-3 toluene 
• 78-92-2 iso-butanol 
• 109-69-3 n-Butyl chloride 
• 71-36-3 butan-1-ol 
• 126-73-8 phosphoric acid tributyl ester 
• 104-15-4 toluene-4-sulfonic acid 
• 78-76-2 s-butyl bromide 
• 109-65-9 1-bromo-butane 
• 78-86-4 s-butyl chloride 
• 75-05-8 acetonitrile 
• 106-97-8 n-butane 
• 22156-91-8 (R)-(-)-s-butyl chloride 
• 593-53-3 Methyl fluoride 

Downstream Products

• 100-21-0 terephthalic acid 
• 92147-01-8 4-sec-butyl-1-methyl-2-nitro-benzene 
• 87-83-2 pentabromotoluene 
• 857563-08-7 1-(5-sec-butyl-2-methyl-phenyl)-ethanone 
• 857562-49-3 1-(4-sec-butyl-2-methyl-phenyl)-ethanone 
• 92546-70-8 3-sek-Butyl-6-methyl-anilin 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 5398-04-9 2-(4-methoxyphenyl)-2-butanol 
• 102934-60-1 4-(1-methylpropyl)-benzenemethanol 
• 34815-72-0 erythro-2-p-tolylbutan-3-ol 
• 34815-72-0 threo-2-p-tolylbutan-3-ol 
• 82166-21-0 methyl cyclohexane 

Relevant academic research and scientific papers

MOF-5 as an efficient heterogeneous catalyst for Friedel-Crafts alkylation reactions

A highly porous metal-organic framework (MOF-5) was synthesized by a solvothermal method, and used as an efficient heterogeneous acid catalyst for Friedel-Crafts alkylation reactions. The solid acid catalyst was characterized using a variety of different techniques, including X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. Quantitative conversion was achieved under mild conditions without the need for an inert atmosphere. The MOF-5 catalyst could be facilely separated from the reaction mixture, and could be reused several times without significant degradation in catalytic activity. Furthermore, no contribution from homogeneous catalysis of active acid species leaching into reaction solution was detected.

METHOD FOR PRODUCING ARENE COMPOUNDS AND ARENE COMPOUNDS PRODUCED BY THE SAME

Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst.

Efficient cross-coupling of aryl Grignard reagents with alkyl halides by recyclable ionic iron(iii) complexes bearing a bis(phenol)-functionalized benzimidazolium cation

A novel bis(phenol)-functionalized benzimidazolium salt, 1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium chloride (H 3LCl, 1), was designed and used to prepare ionic iron(iii) complexes of the type [H3L][FeX4] (X = Cl, 2; X = Br, 3). Both 2 and 3 were characterized by elemental analysis, Raman spectroscopy, electrospray ionization mass spectrometry and X-ray crystallography. The catalytic performances of 2 and 3 in cross-coupling reactions using aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens were studied. This analysis shows that complex 2 has good potential for alkyl chloride-mediated coupling. In comparison, complex 3 showed slightly lower catalytic activity. After decanting the product contained in the ethereal layer, complex 2 could be recycled at least eight times without significant loss of catalytic activity.

IRON BISPHENOLATE COMPLEXES AND METHODS OF USE AND SYNTHESIS THEREOF

The present application, relates to iron bisphenolate complexes and methods of use and synthesis thereof. The iron complexes are prepared from tridentate or tetradentate ligands of Formula I: wherein R1 and R2 are as defined herein. Also provided are methods and processes of using the iron bisphenolate complexes as catalysts in cross-coupling reactions and in controlled radical polymerizations.

Microwave-assisted silica-supported aluminum chloride-catalyzed Friedel-Crafts alkylation

Microwave irradiation is a popular method in organic synthesis to achieve high yields in shorter reaction times. This decreases total 'man-hours' in a synthetic setting. Another technique used in organic chemistry to decrease manual manipulations, is solid support reagents. The benefits of this approach is that upon completion of a reaction, a simple filtration can be performed which expedites the work-up and also produces less organic waste. Friedel-Crafts alkylation has been explored using microwave chemistry as well as with solid-supported reagents. In comparison with traditional heating, as well as with AlCl3, superior yields were observed with silica-gel bound aluminum chloride (Si-AlClx) when microwave irradiated for only 5 min.

Ionic iron(iii) complexes of bis(phenol)-functionalized imidazolium cations: Synthesis, structures and catalysis for aryl Grignard cross-coupling of alkyl halides

A series of bis(phenol)-functionalized imidazolium salts, 1,3-bis(4,6-di-R1-2-hydroxybenzyl)-2-R2-4,5-di-R 3-imidazolium chlorides H3LnCl (R1 = tBu, R2 = R3 = H, H3L 1Cl, 1; R1 = CH3, R2 = R3 = H, H3L2Cl, 2; R1 = tBu, R 2 = H, R3 = Cl, H3L3Cl, 3; R 1 = tBu, R2 = CH3, R3 = H, H3L4Cl, 4), were used to produce a novel series of ionic iron(iii) complexes [H3Ln][FeX4] (n = 1, X = Cl, 5; n = 2, X = Cl, 6; n = 3, X = Cl, 7; n = 4, X = Cl, 8; n = 1, X = Br, 9; n = 3, X = Br, 10). All of the complexes were characterized by Raman spectroscopy and electrospray ionization mass spectrometry. Elemental analysis and X-ray crystallography were also used. All of the complexes were non-hygroscopic and air-stable, with five of them existing as solids (5, 7-10) and one as an oil (6) at room temperature. A preliminary catalytic study on the cross-coupling reactions of aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens, revealed that all of the ionic iron(iii) complexes exhibited good to excellent catalytic activity. Complexes 5, 6 and 8 exhibited optimal activity, whereas 7, 9 and 10 showed only moderate activity. Furthermore, by simply decanting the cross-coupling product in the ether layer, complexes 5 and 6 could be reused in at least seven successive runs without significant loss in catalytic activity.

Catalytic alkylation of aryl Grignard reagents by iron(iii) amine-bis(phenolate) complexes

Reaction of n-propylamino-N,N-bis(2-methylene-4-tert-butyl-6-methylphenol), H2L1, n-propylamino-N,N-bis(2-methylene-4,6-di-tert-butylphenol), H2L2, and benzylamino-N,N-bis(2-methylene-4-tert-butyl-6- methylphenol), H2L3, with anhydrous ferric chloride in the presence of base yields the products, [FeL1(μ-Cl)]2 (1), [FeL2(μ-Cl)]2 (2) and [FeL3(μ-Cl)]2 (3). In the solid state, these complexes exist as chloride-bridged dimers giving distorted trigonal bipyramidal iron(iii) ions. Reaction of H2L1 with FeBr 3, however, results in the formation of a tetrahedral iron(iii) complex possessing two bromide ligands. The amine-bis(phenolate) ligand is bidentate in this complex and bonds to the iron(iii) ion via the phenolate O-donors. The central amine donor is protonated, resulting in a quaternized ammonium fragment and the iron(iii) centre possesses a negative formal charge. As a result, this complex is zwitterionic and formulated as FeBr2L1H (4). Complex 1 is an air-stable, non-hygroscopic, single-component catalyst for C-C cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides, including chlorides. Good to excellent yields of cross-coupled products are obtained in diethyl ether at room temperature. In some cases where low yields are obtained under these conditions, the use of microwave-assisted heating of the reaction mixture can improve yields. The Royal Society of Chemistry 2011.

Direct cobalt-catalyzed cross-coupling between aryl and alkyl halides

An operationally simple cross-coupling reaction between aryl halides and alkyl halides with high selectivity has been developed. The underlying domino process utilizes CoCl2/Me4-DACH as a catalyst system. The methodology exhibits hig

Domino iron catalysis: Direct aryl-alkyl cross-coupling

(Chemical Equation Presented) Striking while the iron is hot: Cheap FeCl3 serves as the precatalyst for the direct cross-coupling of aryl and alkyl halides that is based on the sequence of Grignard formation and subsequent cross-coupling. This

Iron-catalyzed desulfinylative C-C cross-coupling reactions of sulfonyl chlorides with grignard reagents

(Chemical Equation Presented) A friendly couple: Conditions have been uncovered that allow the desulfinylative C-C cross-coupling reaction of inexpensive sulfonyl chlorides and Grignard reagents (see scheme, acac = acetylacetonate, NMP = N-methylpyrrolidone). The reactions rely on environmentally friendly iron catalysts and do not require expensive and/or toxic ligands.