7786-29-0

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Methyloctanal is used as a flavoring agent for enhancing the aroma of various food products, such as beverages, confectionery, and baked goods. Its floral scent adds a pleasant and natural aroma to these products, making them more appealing to consumers.
Used in Perfumery:
In the perfumery industry, 2-methyloctanal is used as a fragrance ingredient to create a fresh, floral, and slightly fruity scent. It is often used in combination with other fragrance compounds to develop unique and complex perfume blends.
Used in Cosmetics:
2-Methyloctanal is also used in the cosmetics industry as a scent component in various personal care products, such as soaps, lotions, and creams. Its floral and fresh scent adds a pleasant aroma to these products, enhancing the overall sensory experience for the user.
Used in Aromatherapy:
In aromatherapy, 2-methyloctanal can be used for its calming and soothing properties. Its floral scent can help create a relaxing atmosphere, promoting a sense of well-being and reducing stress.

Synthesis

By heating methoxymethyl hexyl carbinol with oxalic acid or with anhydrous formic acid; also from hexanal and propionic aldehyde, Darzen’s synthesis of reacting methyl hexyl ketone and ethyl chloroacetate with sodium ethylate; the resulting ester is then hydrolyzed to the acid and this heated under vacuum.

InChI:InChI=1/C9H18O/c1-3-4-5-6-7-9(2)8-10/h8-9H,3-7H2,1-2H3

Upstream product

• 5561-87-5 3-hydroxydecanoic acid 
• 592-41-6 1-hexene 
• 123-38-6 propionaldehyde 
• 6924-86-3 2-hexyl-2-methyloxirane 
• 78-85-3 2-methylpropenal 
• 64889-46-9 n-pentylcopper 
• 36049-78-2 2-iodooctane 
• 201230-82-2 carbon monoxide 
• 111-66-0 oct-1-ene 
• 1809-04-7 (S)-(+)-2-iodooctane 
• 926-64-7 N,N-Dimethylamino acetonitrile 
• 104681-79-0 1-Methoxy-2-methyl-octan-2-ol 
• 113388-59-3 Formic acid (E)-2-methyl-oct-1-enyl ester 
• 557-35-7 2-bromooctane 

Downstream Products

• 111-84-2 nonane 
• 818-81-5 2-methyloctan-1-ol 
• 143-08-8 nonyl alcohol 
• 1453811-63-6 (2S,3S,4S,5S,6S)-1-(4-methoxybenzyloxy)-2,4,6-trimethyldodecane-3,5-diol 
• 1453811-60-3 (2S,3S,4S)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-4-methyldecan-3-ol 
• 1453811-64-7 O-(2R,3S,4S)-2-((4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-4-methyldecan-3-yl (S)-methyl carbonodithioate 
• 1453811-65-8 (4R,5S)-2-(4-methoxyphenyl)-5-methyl-4-((2S,4S)-4-methyldecan-2-yl)-1,3-dioxane 
• 1453811-66-9 (2S,3R,4S,6S)-3-(4-methoxybenzyloxy)-2,4,6-trimethyldodecan-1-ol 
• 1453811-67-0 1-methoxy-4-(((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yloxy)methyl)benzene 
• 1453811-68-1 (S)-((3S,4R,5S,7S)-3,5,7-trimethyltridec-1-en-4-yl) 2-(benzyloxycarbonylamino)propanoate 
• 1453811-56-7 ((2R,3R,4S,6S)-1-(2-tert-butoxy-2-oxoethylamino)-2,4,6-trimethyl-1-oxododecan-3-yl) (S)-2-(benzyloxycarbonylamino)propanoate 
• 1453811-61-4 (2S,4S,5S,6S)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6-trimethyldodecan-3-one 
• 229334-21-8 Gymnastatin H 
• 1269425-15-1 methyl 2-[(2E,4E)-4,6-dimethyldodeca-2,4-dienamido]-3-(4-t-butyldimethylsilyloxyphenyl)-propanoate 

Relevant academic research and scientific papers

Methyl-modified cage-type phosphorus ligand and preparation method thereof Preparation method and application thereof

The invention discloses a methyl-modified cage-type phosphorus ligand, a preparation method and application thereof, in particular to a synthesis design, wherein methyl is further introduced on a phenyl ring of triphenylphosphine, and a methyl-modified cage-type phosphorus ligand is synthesized, and when a methyl meta-substituted cage-type phosphorus ligand is used as a hydroformylation reaction catalyst the proportion of n-structural aldehyde and isomeric aldehyde is 2.6. TOF-1 The methyl-substituted cage-type phosphorus ligand is excellent in performance, stable in property and recyclable, has excellent substrate applicability in the hydroformylation catalytic reaction, has a good industrial application prospect, and has very important significance in metal organic catalysis.

ALDEHYDE GENERATION VIA ALKENE HYDROFORMYLATION

Aldehyde generation includes providing a first input stream, a second input, and an alkene substrate to a reactor system. The first input stream includes a catalyst, a ligand, and an organic solvent. The second input stream includes a mixture of carbon monoxide (CO) and hydrogen gas (H2). The alkene substrate is in either gaseous form or liquid form, the liquid form of the alkene substrate being provided with the first input stream, the gaseous form of the alkene substrate being provided with the second input stream. The reactor system includes a first reactor and a second reactor, where the second reactor is gas permeable and positioned within the first reactor.

Chemo- And regioselective hydroformylation of alkenes with CO2/H2over a bifunctional catalyst

As is well known, CO2 is an attractive renewable C1 resource and H2 is a cheap and clean reductant. Combining CO2 and H2 to prepare building blocks for high-value-added products is an attractive yet challenging topic in green chemistry. A general and selective rhodium-catalyzed hydroformylation of alkenes using CO2/H2 as a syngas surrogate is described here. With this protocol, the desired aldehydes can be obtained in up to 97% yield with 93/7 regioselectivity under mild reaction conditions (25 bar and 80 °C). The key to success is the use of a bifunctional Rh/PTA catalyst (PTA: 1,3,5-triaza-7-phosphaadamantane), which facilitates both CO2 hydrogenation and hydroformylation. Notably, monodentate PTA exhibited better activity and regioselectivity than common bidentate ligands, which might be ascribed to its built-in basic site and tris-chelated mode. Mechanistic studies indicate that the transformation proceeds through cascade steps, involving free HCOOH production through CO2 hydrogenation, fast release of CO, and rhodium-catalyzed conventional hydroformylation. Moreover, the unconventional hydroformylation pathway, in which HCOOAc acts as a direct C1 source, has also been proved to be feasible with superior regioselectivity to that of the CO pathway.

Insight into decomposition of formic acid to syngas required for Rh-catalyzed hydroformylation of olefins

Formic acid (FA) is one kind of important bulk chemicals, which is recognized as a sustainable and eco-friendly energy carrier to transport H2 via dehydrogenation or CO via decarbonylation. Expectantly, FA upon decomposition into H2 and CO could be used as the syngas alternative for hydroformylation. In this paper, the behaviors of FA to release H2 as well as CO following the distinct pathways were carefully investigated for the first time, and then established a new hydroformylation protocol free of syngas. It was found that the atmospheric hydroformylation of olefins with formic acid (FA) as syngas alternative was smoothly fulfilled over Xantphos (L1) modified Rh-catalyst under mild conditions (80 °C, Rh concentration 1 mol %, 14 h), resulting in >90% conversion of the olefins along with the high selectivity to the target aldehydes (>93%). By using FA as syngas source, the side-reaction of olefin-hydrogenation was greatly depressed. The in situ FT-IR and the high-pressure 1H NMR spectroscopic analyses were applied to reveal how FA behaves dually as CO surrogate and hydrogen source over L1-Rh(acac)(CO)2 catalytic system, based on which the deeply insight into the catalytic mechanism of hydroformylation of olefins with FA as syngas alternative was offered.

Rh-catalyzed highly regioselective hydroformylation to linear aldehydes by employing porous organic polymer as a ligand

In this work, we developed a new structural porous organic polymer containing biphosphoramidite unit, which can be used as a solid bidentate phosphorous ligand for rhodium-catalyzed solvent-free higher olefins hydroformylation. The resultant catalyst demonstrated unprecedently high regioselectivity to linear aldehydes and could be readily recovered for successive reuses with good stability in both catalytic activity and regioselectivity. This journal is

Bimetallic Paddlewheel-type Dirhodium(II,II) Acetate and Formamidinate Complexes: Synthesis, Structure, Electrochemistry, and Hydroformylation Activity

Classical hydroformylation catalysts use mononuclear rhodium(I) complexes as precursors; however, very few examples of bimetallic systems have been reported. Herein, we report fully substituted dirhodium(II,II) complexes (C1-C6) containing acetate and diphenylformamidinate bridging ligands (L1-L4). The structure and geometry around these paddlewheel-type, bimetallic cores were confirmed by single-crystal X-ray diffraction. The complexes C3-C6 show electrochemical redox reactions, with the expected reduction (Rh24+/3+) and two oxidation (Rh24+/5+ and Rh25+/6+) electron transfer processes. Furthermore, the bimetallic complexes were evaluated as catalyst precursors for the hydroformylation of 1-octene, with the acetate-containing complexes (C1 and C2) showing near quantitative conversion (>99%) of 1-octene, excellent activity and chemoselectivity toward aldehydes (>98%), with moderate regioselectivity toward linear products. Replacement of the acetate with diphenylformamidinate ligands (complexes C3-C6) yielded moderate-to-good chemoselectivity and regioselectivity, favoring linear aldehydes.

Integration of phosphine ligands and ionic liquids both in structure and properties-a new strategy for separation, recovery, and recycling of homogeneous catalyst

The major limitation of classic biphasic ionic liquid (IL) catalysis is the heavy use of solvent ILs, which not only violates green chemistry principles but also even worsens catalytic efficiency. So it has always been a challenge finding ways to use ILs more efficiently, economically, and greenly to construct highly effective and long term stable IL catalytic systems. In this work, we synthesized a class of room temperature phosphine-functionalized polyether guanidinium ionic liquids (RTP-PolyGILs) by a convenient ion exchange reaction of polyether guanidinium ionic liquids (PolyGILs) with phosphine-sulfonate ligands based on the concept of the integration of both the phosphine ligand and IL. The resulting RTP-PolyGILs existed as liquids at room temperature and possessed dual functions of both the phosphine ligand and solvent IL; therefore they could both form catalysts by complexing with transition metals and act as catalyst carriers, thus achieving the integration of phosphine ligands with ILs both in structure and properties. Based on the unique properties of these multi-functional integrated RTP-PolyGILs, we constructed a highly effective homogeneous catalysis-biphasic separation (HCBS) system for Rh-catalyzed hydroformylation of higher olefins using only a catalytic amount of RTP-PolyGILs (equivalent to 0.025-0.4 mol% of 1-alkenes). Our HCBS system could be flexibly regulated with regard to catalytic performance (activity and linear selectivity) by changing the structure or type of the sulfonated ligand anion on RTP-PolyGILs. Specifically, it presented a TOF value of 3000-26000 h-1 and a linear selectivity of 68%-98% (corresponding to the l/b ratio of 2.2-37.5) with a total turnover number (TTON) of 11000-45000 and an extremely low Rh leaching of only 0.02-0.4 ppm. Therefore, the HCBS system can effectively combine the advantages of both homogeneous (high activity and good selectivity) and biphasic catalysis (easy catalyst separation). We additionally extended the application of the HCBS system to the hydrogenation of olefins to demonstrate the universality of the RTP-PolyGILs in catalytic reactions.

XL-Xantphos: Design and Synthesis of a Mechanistic Probe of Xantphos O-Coordination in Catalytic Reactions

The synthesis and characterization of an analog of the Xantphos ligand that is geometrically incapable of coordination of the xanthene bridging oxygen atom is reported. This new ligand, XL-Xantphos, ((9,9-dimethyl-9H-xanthene-4,5-diyl)bis(4,1-phenylene))bis(diphenylphosphane), was studied in homogeneous, catalytic reactions for comparison with Xantphos. The XL-Xantphos ligand performed essentially identically to Xantphos in Rh-catalyzed hydroformylation of 1-octene, which suggests that the high regioselectivity for linear aldehyde is due to the large bite angle of these ligands and is not influenced by oxygen coordination to the metal. The Pd-catalyzed amidocarbonylation of 4-bromoanisole with dimethylhydroxylamine hydrochloride similarly showed no difference between Xantphos and XL-Xantphos. Computations on Pd(II) phosphine complexes at the DLPNO-CCSD(T) level of theory indicated that these ligands have different preferences for cis and trans coordination modes. The XL-Xantphos ligand has a thermodynamic preference for trans-chelated structures, whereas the cis-[(Xantphos)PdCl2] isomer was calculated to be thermodynamically more stable than its trans isomer. Given the key role of d8 square planar Pd intermediates in many catalytic cycles, the greater preference of Xantphos to form cis chelates may indeed be a factor which has made this ligand particularly effective.

HYDROFORMYLATION METHOD AND CATALYST USING RHODIUM-RUTHENIUM DUAL METAL AND TETRADENTATE PHOSPHINE LIGAND

A homogeneous catalytic reaction method and a catalyst for isomerization and hydroformylation of long-chain internal olefins are disclosed. A rhodium-ruthenium metal complex is used as a catalyst; and the ligands are tetradentate phosphine ligands. By means of the catalytic system, homogeneous internal olefin isomerization aid hydroformylation can be performed under a certain temperature and pressure to obtain aldehyde products having high normal to iso ratios. The present invention is applicable to not only long-chain internal olefins (≥C8) but also internal olefins having a carbon number less than 8.

Porous organic polymer supported rhodium as a reusable heterogeneous catalyst for hydroformylation of olefins

A new porous organic polymer has been prepared via copolymerization of divinyl-functionalized phosphoramidite ligand and tris(4-vinylphenyl)phosphine. The porous polymer was loaded with Rh(acac)CO2 to yield a supported Rh catalyst, which demonstrated good regioselectivity (l/b = 6.7-52.8) and high catalytic activity (TON up to 45.3 × 104) in hydroformylation of terminal and internal olefins. Remarkably, the heterogeneous catalyst can be reused at least 10 cycles without losing activity and selectivity in hydroformylation of 1-hexene.