600-36-2

Usage

Chemical Properties

clear colorless liquid

Uses

2,4-Dimethyl-3-pentanol was used as a proton source in the diastereoselective coupling with 2-substituted acrylate derivatives. It was used in the polymerization of 1,1′-(1,3-phenylene) diethanol (1,3-diol) and diisopropyl adipate.

InChI:InChI=1/C7H16O/c1-5(2)7(8)6(3)4/h5-8H,1-4H3

Upstream product

• 558-30-5 2-methyl-1,2-epoxypropane 
• 920-39-8 isopropylmagnesium bromide 
• 4390-75-4 2-hydroxy-2-isopropyl-3-methyl-butyronitrile 
• 927-77-5 n-propylmagnesium bromide 
• 100-66-3 methoxybenzene 
• 565-80-0 2,4-dimethylpentan-3-one 
• 60-29-7 diethyl ether 
• 78-84-2 isobutyraldehyde 
• 1068-55-9 isopropylmagnesium chloride 
• 79-22-1 methyl chloroformate 
• 71-23-8 propan-1-ol 
• 693-03-8 n-butyl magnesium bromide 
• 10557-57-0 propylmagnesium iodide 
• 64-17-5 ethanol 

Downstream Products

• 34557-54-5 methane 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 98-86-2 acetophenone 
• 3623-52-7 isomenthol 
• 24910-63-2 2,3-dimethyl-pent-2-ene 
• 625-65-0 2,4-dimethyl-2-pentene 
• 4083-57-2 2,4-dimethylpent-3-ylamine 
• 565-80-0 2,4-dimethylpentan-3-one 
• 107821-08-9 2,4-dimethylpentan-3-yl benzoate 
• 4406-52-4 (1,1,3-trimethylbutyl)benzene 
• 33104-11-9 4-Hydroxy-1-(1.1.3-trimethyl-butyl)-benzol 
• 21991-16-2 C₁₅H₁₉NO₆ 
• 57741-77-2 Phosphoric acid benzyl ester 1-isopropyl-2-methyl-propyl ester 1-methyl-2-oxo-propyl ester 
• 130427-36-0 (1S,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-(1-isopropyl-2-methyl-propoxy)-2-oxa-5-thia-bicyclo[2.2.2]octane 

Relevant academic research and scientific papers

CATALYSIS WITH TRICARBONYL-tetrahapto-CYCLOPENTADIENONERUTHENIUM(0) COMPLEXES. A WATER-GAS TYPE REACTION

With water tricarbonyl-tetrahapto-tetraphenylcyclopentadienoneruthenium(0) (1) undergoes a water-gas type reaction whereby a coordinated CO is oxidized to CO2, and gives the dimeric complex, which was isolated in high yield.A catalytic reduction of ketones with CO and water under mild conditions has been developed, and a catalytic cycle proposed.A turnover frequency of 1.2 min-1, which is increased by a factor of ca. 6 by the presence of sodium carbonate, has been observed in the reactions with cyclohexanone.

Highly efficient NHC-iridium-catalyzed β-methylation of alcohols with methanol at low catalyst loadings

The methylation of alcohols is of great importance since a broad number of bioactive and pharmaceutical alcohols contain methyl groups. Here, a highly efficient β-methylation of primary and secondary alcohols with methanol has been achieved by using bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complexes. Broad substrate scope and up to quantitative yields were achieved at low catalyst loadings with only hydrogen and water as by-products. The protocol was readily extended to the β-alkylation of alcohols with several primary alcohols. Control experiments, along with DFT calculations and crystallographic studies, revealed that the ligand effect is critical to their excellent catalytic performance, shedding light on more challenging Guerbet reactions with simple alcohols. [Figure not available: see fulltext.].

A Practical and Stereoselective In Situ NHC-Cobalt Catalytic System for Hydrogenation of Ketones and Aldehydes

Homogeneous catalytic hydrogenation of carbonyl groups is a synthetically useful and widely applied organic transformation. Sustainable chemistry goals require replacing conventional noble transition metal catalysts for hydrogenation by earth-abundant base metals. Herein, we report how a practical in situ catalytic system generated by easily available pincer NHC precursors, CoCl2, and a base enabled efficient and high-yielding hydrogenation of a broad range of ketones and aldehydes (over 50 examples and a maximum turnover number [TON] of 2,610). This is the first example of NHC-Co-catalyzed hydrogenation of C=O bonds using flexible pincer NHC ligands consisting of a N-H substructure. Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized by fine-tuning of the steric bulk of pincer NHC ligands. Additionally, a bis(NHCs)-Co complex was successfully isolated and fully characterized, and it exhibits excellent catalytic activity that equals that of the in-situ-formed catalytic system. Catalytic hydrogenation is a powerful tool for the reduction of organic compounds in both fine and bulk chemical industries. To improve sustainability, more ecofriendly, inexpensive, and earth-abundant base metals should be employed to replace the precious metals that currently dominate the development of hydrogenation catalysts. However, the majority of the base-metal catalysts that have been reported involve expensive, complex, and often air- and moisture-sensitive phosphine ligands, impeding their widespread application. From a mixture of the stable CoCl2, imidazole salts, and a base, our newly developed catalytic system that formed easily in situ enables efficient and stereoselective hydrogenation of C=O bonds. We anticipate that this easily accessible catalytic system will create opportunities for the design of practical base-metal hydrogenation catalysts. A practical in situ catalytic system generated by a mixture of easily available pincer NHC precursors, CoCl2, and a base enabled highly efficient hydrogenation of a broad range of ketones and aldehydes (over 50 examples and up to a turnover number [TON] of 2,610). Diastereodivergent hydrogenation of substituted cyclohexanone derivatives was also realized in high selectivities. Moreover, the preparation of a well-defined bis(NHCs)-Co complex via this pincer NHC ligand consisting of a N-H substructure was successful, and it exhibits equally excellent catalytic activity for the hydrogenation of C=O bonds.

Transfer Hydrogenation of Carbonyl Groups, Imines and N-Heterocycles Catalyzed by Simple, Bipyridine-Based MnI Complexes

Utilization of hydroxy-substituted bipyridine ligands in transition metal catalysis mimicking [Fe]-hydrogenase has been shown to be a promising approach in developing new catalysts for hydrogenation. For example, MnI complexes with 6,6′-dihydroxy-2,2′-bipyridine ligand have been previously shown to be active catalysts for CO2 hydrogenation. In this work, simple bipyridine-based Mn catalysts were developed that act as active catalysts for transfer hydrogenation of ketones, aldehydes and imines. For the first time, Mn-catalyzed transfer hydrogenation of N-heterocycles was reported. The highest catalytic activity among complexes with variously substituted ligands was observed for the complex bearing two OH groups in bipyridine. Deuterium labeling experiments suggest a monohydride pathway.

Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ3-Iodanes

The site-selective and chemoselective functionalization of alcohols in complex polyols remains a formidable synthetic challenge. Whereas significant advancements have been made in selective derivatization at the oxygen center, chemoselective oxidation to the corresponding carbonyls is less developed. In cyclic systems, whereas the selective oxidation of axial alcohols is well known, a complementary equatorial selective process has not yet been reported. Herein we report the utility of nitrogen-ligated (bis)cationic λ3-iodanes (N-HVIs) for alcohol oxidation and their unprecedented levels of selectivity for the oxidation of equatorial over axial alcohols. The conditions are mild, and the simple pyridine-ligated reagent (Py-HVI) is readily synthesized from commercial PhI(OAc)2 and can be either isolated or generated in situ. Conformational selectivity is demonstrated in both flexible 1,2-substituted cyclohexanols and rigid polyol scaffolds, providing chemists with a novel tool for chemoselective oxidation.

PROCESS FOR MAKING FORMIC ACID UTILIZING LOWER-BOILING FORMATE ESTERS

Disclosed is a process for recovering formic acid from a formate ester of a C3 to C4 alcohol. Disclosed is also a process for producing formic acid by carbonylating a C3 to C4 alcohol, hydrolyzing the formate ester of the alcohol, and recovering a formic acid product. The alcohol may be dried and returned to the reactor. The process enables a more energy efficient production of formic acid than the carbonylation of methanol to produce methyl formate.

Carbonyl and ester C-O bond hydrosilylation using κ4-diimine nickel catalysts

The synthesis of alkylphosphine-substituted α-diimine (DI) ligands and their subsequent addition to Ni(COD)2 allowed for the preparation of (iPr2PPrDI)Ni and (tBu2PPrDI)Ni. The solid state structures of both compounds were found to feature a distorted tetrahedral geometry that is largely consistent with the reported structure of the diphenylphosphine-substituted variant, (Ph2PPr DI)Ni. To explore and optimize the synthetic utility of this catalyst class, all three compounds were screened for benzaldehyde hydrosilylation activity at 1.0 mol% loading over 3 h at 25 °C. Notably, (Ph2PPr DI)Ni was found to be the most efficient catalyst while phenyl silane was the most effective reductant. A broad scope of aldehydes and ketones were then hydrosilylated, and the silyl ether products were hydrolyzed to afford alcohols in good yield. When attempts were made to explore ester reduction, inefficient dihydrosilylation was noted for ethyl acetate and no reaction was observed for several additional substrates. However, when an equimolar solution of allyl acetate and phenyl silane was added to 1.0 mol% (Ph2PPr DI)Ni, complete ester C-O bond hydrosilylation was observed within 30 min at 25 °C to generate propylene and PhSi(OAc)3. The scope of this reaction was expanded to include six additional allyl esters, and under neat conditions, turnover frequencies of up to 990 h-1 were achieved. This activity is believed to be the highest reported for transition metal-catalyzed ester C-O bond hydrosilylation. Proposed mechanisms for (Ph2PPr DI)Ni-mediated carbonyl and allyl ester C-O bond hydrosilylation are also discussed.

“Inverse” Frustrated Lewis Pairs: An Inverse FLP Approach to the Catalytic Metal Free Hydrogenation of Ketones

For the first time have boron-containing weak Lewis acids been demonstrated to be active components of Frustrated Lewis Pair (FLP) catalysts in the hydrogenation of ketones to alcohols. Combining the organosuperbase (pyrr)3P=NtBu with the Lewis acid 9-(4-CF3-C6H4)-BBN generated an “inverse” FLP catalyst capable of hydrogenating a range of aliphatic and aromatic ketones including N-, O- and S-functionalized substrates and bio-mass derived ethyl levulinate. Initial computational and experimental studies indicate the mechanism of catalytic hydrogenation with “inverse” FLPs to be different from conventional FLP catalysts that contain strong Lewis acids such as B(C6F5)3.

A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives

A versatile iridium(III) metallacycle catalysed rapidly and selectively the reduction of a large array of challenging esters and carboxylic acids as well as various ketones and aldehydes. The reactions proceeded in high yields at room temperature by hydrosilylation followed by desilylation. Although the reactions of various aldehydes and ketones resulted exclusively in alcohols, the hydrosilylation of esters led to alcohols or ethers, depending on the type of substrate. Regarding the carboxylic acids, again the nature of the reagent controlled the outcome of the hydrosilylation reaction, either alcohols or aldehydes being formed.

CATALYST AND METHOD FOR HYDROGENATION OF 1,3-CYCLOBUTANEDIKETONE COMPOUND

Catalyst for hydrogenation of 1,3-cyclobutanediketone compound is provided, which includes a support and VIIIB group transition metal loaded thereon. The support includes a first oxide powder with a surface wrapped by a second oxide. The first oxide includes silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, zinc oxide, or a combination thereof. The second oxide has a composition of MxAl(1-x)O(3-x)/2, M is alkaline earth metal, and x is from 0.3 to 0.7.