690-37-9

Usage

Uses

Used in Biodegradation Studies:
2,4,4-Trimethyl-2-pentanol is used as an intermediate in the study of the biodegradation process of xeno-estrogenic octylphenol by the Sphingomonas sp. strain. 2,4,4-TRIMETHYL-2-PENTANOL plays a crucial role in understanding the metabolic pathways and enzymatic reactions involved in the breakdown of environmental pollutants.
Used in Comparative Binding Affinity Studies:
2,4,4-Trimethyl-2-pentanol is used as a reference compound in studies comparing the relative binding affinities of low-molecular-weight proteins from humans versus male rats. This application helps researchers to better understand the differences in protein-ligand interactions between species, which can be valuable for drug development and toxicological assessments.

InChI:InChI=1/C8H18O/c1-7(2,3)6-8(4,5)9/h9H,6H2,1-5H3

Upstream product

• 107-39-1 2,4,4-trimethyl-1-pentene 
• 6111-88-2 2-chloro-2,4,4-trimethylpentane 
• 75-05-8 acetonitrile 
• 96-06-0 2,3-epoxy-2,4,4-trimethylpentane 
• 107-48-2 2-methyl-2-neopentyl-oxirane 
• 5809-08-5 1,1,3,3-tetramethylbutyl hydroperoxide 
• 926-13-6 peroxyacetic acid 1,1,3,3-tetramethyl-butyl ester 
• 55705-72-1 Neopentyl-dimethylcarbinyl-p-nitrobenzoat 
• 917-64-6 methyl magnesium iodide 
• 10250-48-3 methyl 3,3-dimethylbutyrate 
• 540-84-1 2,2,4-trimethylpentane 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 67-56-1 methanol 
• 55204-43-8 2,2'-Azobis(2,4,4-trimethylpentane) 

Downstream Products

• 88593-00-4 3-piperidino-propionic acid-(1,1,3,3-tetramethyl-butylamide) 
• 100392-27-6 N,N-dimethyl-glycine-(1,1,3,3-tetramethyl-butylamide) 
• 102013-99-0 2-diethylamino-heptanoic acid-(1,1,3,3-tetramethyl-butylamide) 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 62574-65-6 2-bromo-2,4,4-trimethylpentane 
• 873393-29-4 2-iodo-2,4,4-trimethyl-pentane 
• 3302-09-8 2,4,4-trimethylpentanoic acid 
• 140-66-9 tert-octylphenol 
• 6111-88-2 2-chloro-2,4,4-trimethylpentane 
• 27540-75-6 1,1,3,3-tetramethylbutyl acetate 
• 74785-64-1 ethyl N-(1,1,3,3-tetramethylbutoxy)carbamate 
• 5809-08-5 1,1,3,3-tetramethylbutyl hydroperoxide 
• 98-54-4 para-tert-butylphenol 

Relevant academic research and scientific papers

Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates

Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.

METHOD FOR PRODUCING OXIDE

PROBLEM TO BE SOLVED: To provide a method for producing an oxide capable of easily producing an oxide excellent in substrate selectivity with a high yield, which allows the reaction to proceed without using a solvent under moderate conditions at 100°C or less. SOLUTION: There is provided a method for producing an oxide by oxidizing a substrate (A) in the presence of a compound selected from oxygen, ozone and a radical generator to obtain a corresponding oxide. The radical generator preferably includes at least one compound selected from a nitroxy-based radical generator and an azo-based radical generator. In addition, the oxidation reaction is preferably carried out in the presence of a metal compound containing at least one metal element selected from cobalt, manganese, zirconium and molybdenum. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT

Alkane oxidation by the system 'tert-butyl hydroperoxide-[Mn 2L2O3][PF6]2 (L = 1,4,7trimethyl-1,4,7-triazacyclononane)-carboxylic acid'

The kinetics of cyclohexane (CyH) oxygenation with terf-butyl hydroperoxide (TBHP) in acetonitrile at 50°C catalysed by a dinuclear manganese(IV) complex 1 containing 1,4,7-trimethyl-1,4,7-triazacyclononane and co-catalysed by oxalic acid have been studied. It has been shown that an active form of the catalyst (mixed-valent dimeric species 'MnIIIMnIV,) is generated only in the interaction between complex 1 and TBHP and oxalic acid in the presence of water. The formation of this active form is assumed to be due to the hydrolysis of the Mn - O - Mn bonds in starting compound 1 and reduction of one MnIV to MnIII. A species which induces the CyH oxidation is radical tert-BuO generated by the decomposition of a monoperoxo derivative of the active form. The constants of the equilibrium formation and the decomposition of the intermediate adduct between TBHP and 1 have been measured: k = 7.4mol-1dm3 and k = 8.4 × 10 -2s-1, respectively, at [H2O] = 1.5 mol dm -3 and [oxalic acid] = 10-2 mol dm-3. The constant ratio for reactions of the monomolecular decomposition of tert-butoxy radical (tert-BuO → CH3COCH3+ CH3) and its interaction with the CyH (terf-BuO + CyH → fert-BuOH + Cy) was calculated: 0.26 mol dm-3. One of the reasons why oxalic acid accelerates the oxidation is due to the formation of an adduct between oxalic acid and 1 (K ≈ 103 mol-1 dm3). Copyright

Hydroperoxidation of alkanes with hydrogen peroxide catalyzed by aluminium nitrate in acetonitrile

The first example of alkane oxygenation with hydrogen peroxide catalyzed by a non-transition metal derivative (aluminium) is reported. Heating (70 °C) a solution of an alkane, RH, hydrogen peroxide (70% aqueous) and a catalytic amount of Al(NO3)3·9H2O in air for a few hours afforded the corresponding alkyl hydroperoxide, ROOH. With cyclooctane, the hydroperoxide yield attained 31% and the maximum turnover number was 150. It is proposed on the basis of measurements of the selectivity parameters for the oxidation of linear and branched alkanes and a kinetic study that the oxidation occurs with the participation of hydroxyl radicals.

Oxidations catalyzed by osmium compounds. Part 1: Efficient alkane oxidation with peroxides catalyzed by an olefin carbonyl osmium(0) complex

A carbonyl osmium(0) complex with π-coordinated olefin, (2,3-η-1,4-diphenylbut-2-en-1,4-dione)undecacarbonyl triangulotriosmium (1), efficiently catalyzes oxygenation of alkanes (cyclohexane, cyclooctane, n-heptane, isooctane, etc.) with hydrogen peroxide, as well as with tert-butyl hydroperoxide and meta-chloroperoxybenzoic acid in acetonitrile solution. Alkanes are oxidized to corresponding alcohols, ketones (aldehydes) and alkyl hydroperoxides. Thus, heating cyclooctane with the 1-H2O2 combination at 70 °C gave products with turnover number as high as 2400 after 6 h. The maximum obtained yield of all products was equal to 20% based on cyclohexane and 30% based on H2O2. The oxidation of linear and branched alkanes exhibits very low regio- and bond-selectivity parameters and this testifies that the reaction proceeds via attack of hydroxyl radicals on C-H bonds of the alkane. The oxygenation products were not formed when the reaction was carried out under argon atmosphere and it can be thus concluded that the oxygenation occurs via the reaction between alkyl radicals and atmospheric oxygen. In summary, the Os(0) complex is much more powerful generator of hydroxyl radicals than any soluble derivative of iron (which is an analogue of osmium in the Periodic System).

Oxidations by the system "hydrogen peroxide-[Mn2L 2O3][PF6]2 (L = 1,4,7-trimethyl-1,4, 7-triazacyclononane)-oxalic acid". Part 6. Oxidation of methane and other alkanes and olefins in water

Oxidation of alkanes with hydrogen peroxide in water solution at 10-50 °C is efficiently catalyzed by the cationic dinuclear manganese (IV) derivative [Mn2L2O3]2+ (1, with L = 1,4,7-trimethyl-1,4,7-triazacyclononane, TMTACN) in the form of the hexafluorophosphate salt ([1][PF6]2) if oxalic acid is present as a co-catalyst. Methane gives methanol and formaldehyde (turnover numbers, TONs, were 7 and 2, respectively, after reduction of the reaction mixture with ascorbic acid) whereas cyclohexane was oxidized with TONs up to 160 affording cyclohexyl hydroperoxide, cyclohexanone and cyclohexanol (the ketone was the main product, although at room temperature almost pure alkyl hydroperoxide was formed). In contrast to the oxidation in acetonitrile, the reaction with linear n-alkanes in water exhibits an unusual distribution of oxygenates. For example, in the oxidation of n-heptane the normalized reactivity of the methylene group in position 4 of the chain is 3-7 times higher than that of the CH2 group in position 2. Dec-1-ene is epoxidized by hydrogen peroxide in water (a biphasic system) catalyzed by [1][PF6] 2 and oxalic acid in the presence of a small amount of acetonitrile with TONs up to 1000 (no epoxidation has been detected in the absence of MeCN).

Alkane oxygenation with H2O2 catalysed by FeCl 3 and 2,2′-bipyridine

The H2O2-FeCl3-bipy system in acetonitrile efficiently oxidises alkanes predominantly to alkyl hydroperoxides. Turnover numbers attain 400 after 1 h at 60°C. It has been assumed that bipy facilitates proton abstraction from a H2O2 molecule coordinated to the iron ion (these reactions are stages in the catalytic cycle generating hydroxyl radicals from the hydrogen peroxide). Hydroxyl radicals then attack alkane molecules finally yielding the alkyl hydroperoxide.

Catalytic oxidation of C-H bonds

The invention provides a catalytic, chemospecific and stereospecific method of oxidizing a wide variety of substrates without unwanted side reactions. Essentially, the method of the instant invention, under relatively mild reaction conditions, catalytically, stereospecifically and chemospecifically inserts oxygen into a hydrocarbon C—H bond. Oxidation (oxygen insertion) at a tertiary C—H bond to form an alcohol (and in some cases a hemiacetal) at the tertiary carbon is favored. The stereochemistry of an oxidized tertiary carbon is preserved. Ketones are formed by oxidizing a secondary C—H bond and ring-cleaved diones are formed by oxidizing cis tertiary CH bonds.

Chemospecific chromium[VI] catalyzed oxidation of C-H bonds at -40 °C

H5IO6 in the presence of catalytic chromoyl diacetate is a powerful method for oxidation of C-H bonds. Tertiary and oxygen activated C-H bonds are oxidized to tertiary alcohols or ketones at temperatures as low as -40 °C. The putative reagent is neutral dioxoperoxy chromium[VI] which undergoes C-H oxidation with retention of stereochemistry. This reagent appears to be the first reagent capable of oxidation of a C-H bond in the presence of an olefin without concomitant epoxidation. Copyright

Alkane oxygenation catalysed by gold complexes

Gold(III) and gold(I) complexes, NaAuCl4 and ClAuPPh3, efficiently catalyse the oxidation of alkanes by H2O2 in acetonitrile solution at 75°C. Turnover numbers (TONs) attain 520 after 144 h. Alkyl hydroperoxides are the main products, whereas ketones (aldehydes) and alcohols are formed in smaller concentrations. It is suggested on the basis of the bond selectivity study that at least one of the pathways in Au-catalysed alkane hydroperoxidation does not involve the participation of free hydroxyl radicals. Possibly, the oxidation begins from the alkane hydrogen atom abstraction by a gold oxo species. The oxidation of cyclooctane by air at room temperature catalysed by NaAuCl4 in the presence of Zn/CH3COOH as a reducing agent and methylviologen as an electron-transfer agent gave cyclooctanol (TON=10).