2109-98-0

Usage

Uses

Used in Food Industry:
2,3-dimethylbutyraldehyde is used as a flavoring agent for enhancing the taste and aroma of various food products. Its strong, pungent odor makes it suitable for adding unique flavors to different types of food items.
Used in Cosmetics Industry:
In the cosmetics industry, 2,3-dimethylbutyraldehyde is used as a fragrance ingredient to provide pleasant and appealing scents to various cosmetic products, such as perfumes, lotions, and creams.
Used in Pharmaceutical Industry:
2,3-dimethylbutyraldehyde is utilized in the production of pharmaceuticals, where it serves as a key component in the synthesis of various medicinal compounds.
Used in Organic Compounds Production:
It is also used in the production of other organic compounds, where its unique chemical properties contribute to the development of new and innovative products.

InChI:InChI=1/C6H12O/c1-5(2)6(3)4-7/h4-6H,1-3H3

Upstream product

• 5870-68-8 ethyl 3-methylpentanoate 
• 66553-15-9 2,3-Dimethyl-1,2-Butanediol 
• 53892-35-6 1-methoxy-2,3-dimethyl-butan-2-ol 
• 26903-66-2 2-isopropylallyl alcohol 
• 563-80-4 3-methyl-butan-2-one 
• 105-39-5 chloroacetic acid ethyl ester 
• 920-39-8 isopropylmagnesium bromide 
• 78-95-5 chloroacetone 
• 590-86-3 isovaleraldehyde 
• 74-88-4 methyl iodide 
• 72221-03-5 2,3-dimethyl-1,2-epoxybutane 
• 79-29-8 2,3-dimethylbutane 
• 35603-21-5 ergost-22-en-3-one 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 2109-23-1 2-Methyl-2-(1-methylethyl)-1,3-propandiol 
• 2109-97-9 (+/-)-2,3-dimethyl-butyraldehyde-(2,4-dinitro-phenylhydrazone) 
• 103867-67-0 (E)-5,6-Dimethyl-1-(toluene-4-sulfinyl)-hept-1-en-4-ol 
• 103867-62-5 5,6-Dimethyl-3-(toluene-4-sulfinyl)-hept-1-en-4-ol 
• 105337-06-2 2-benzyl-3-methylbutanal 
• 19550-30-2 2,3-dimethylbutanol 
• 13702-58-4 3,4,6-trimethyl-3-cyclohexene-1-carbaldehyde 
• 35161-12-7 4-Isopropyl-4-methyl-cyclohex-2-enone 
• 98215-21-5 1-(Dimethyl-hydrazono)-4,5-dimethyl-1-phenyl-hexan-3-ol 
• 98215-29-3 3-hydroxy-4,5-dimethyl-1-phenylhexan-1-one 
• 57074-19-8 5,6-dimethyl-hept-3t-en-2-one 
• 142787-76-6 (Z)-5,6-dimethylhept-4-en-2-one 
• 142787-70-0 (E)-5,6-dimethylhept-4-en-2-one 
• 14287-61-7 2,3-dimethylbutyric acid 

Relevant academic research and scientific papers

The CO/PC analogy in coordination chemistry and catalysis

This short account summarizes recent results obtained in the coordination chemistry of phosphinines and emphasizes their analogy with CO ligands. Reduced complexes can be easily assembled through the reaction of reduced 2,2′-biphosphinine dianions with transition metal fragments. Theoretical calculations were performed to establish the oxidation state of the metal in these complexes. Though many reduced complexes are available, phosphinines proved to be too sensitive toward nucleophiles to be used as efficient ligands in most catalytic processes. However, the high electrophilicity of the phosphorus atom can be exploited to synthesize phosphacylohexadienyl anions which exhibit a surprising coordination chemistry. When phosphino sulfide groups are incorporated as ancillary tridentate anionic SPS ligands can be easily produced. These ligands can bind different transition metal fragments such as M-X (M = group 10 metal, X = halogen), Rh-L (L = 2 electron donor ligand), Cu-X and Au-X (X = halogen). Palladium(II) complexes proved to be active catalyst in the Miyaura cross-coupling reaction. Bidentate anionic PS ligands were also synthesized following a similar approach. Their Pd(II) (allyl) derivatives showed a very good activity in the Suzuki catalyzed cross-coupling process that allows the synthesis of biphenyl derivatives through the reaction of phenylboronic acid with bromoarenes.

Method for synthesizing fluorescent dye intermediate aldehyde by hydroformylation of 1,3-diene compound

The invention discloses a method for synthesizing a fluorescent dye intermediate aldehyde by hydroformylation of 1,3-diene compound. The method comprises the following steps: S1, sequentially adding 0.01 mmol (1 mol%) of [Rh(cod)Cl]2, 0.1 mmol of a phosphine ligand(P/Rh=10/1) and 1 mmol of diene into a reaction flask, adding 1 ml of a solvent DMF, putting the reaction flask into a high-pressure reaction kettle, after the reaction is finished, transferring a mixed solution into a 25 mL glass bottle with 200 microliters of n-tridecane as an internal standard by using a rubber head dropper, and detecting; and S2, determining the product yield and the structure through a gas chromatograph and a nuclear magnetic resonance spectrum, wherein the obtained olefin conversion rate is larger than 99%, the aldehyde yield ranges from 61% to 99%, and the regioselectivity of the product aldehyde ranges from 70/30 to 100/0. According to the method disclosed by the invention, the separation and purification steps of aldehyde products are simplified, and the substrate of the dialkene hydroformylation reaction is excellent in universality.

Ligand-Controlled Direct Hydroformylation of Trisubstituted Olefins

The direct hydroformylation of trisubstituted olefins has been achieved with a combination of a Rh(I) catalyst and a π-acceptor phosphorus (briphos) ligand. A sterically bulky briphos ligand with a large cone angle that forms a 1:1 complex with Rh(I) is found to be reactive for the hydroformylation of trisubstituted olefins. The aldehyde products were obtained with high diastereoselectivity (>99:1) and regioselectivity (49%-81%).

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: Possible route to the 4-methylpregabalin core structure

Chiral derivatives of γ-aminobutyric acid are widely used as medicines and can be obtained by organocatalytic Michael additions. We show here the stereoselective synthesis of 4-methylpregabalin stereoisomers using a Michael addition of dimethyl malonate to a racemic nitroalkene. The key step of the synthesis operates as a kinetic resolution with a chiral squaramide catalyst. Furthermore, specific organocatalysts can provide respective stereoisomers of the key Michael adduct in up to 99:1 er.

Chiral propargylic cations as intermediates in SN1-type reactions: Substitution pattern, nuclear magnetic resonance studies, and origin of the diastereoselectivity

Nine propargylic acetates, bearing a stereogenic center (-C*HXR 2) adjacent to the electrophilic carbon atom, were prepared and subjected to SN1-type substitution reactions with various silyl nucleophiles employing bismuth trifluoromethanesulfonate [Bi(OTf)3] as the Lewis acid. The diastereoselectivity of the reactions was high when the alkyl group R2 was tertiary (tert-butyl), irrespective of the substituent X. Products were formed consistently with a diastereomeric ratio larger than 95:5 in favor of the anti-diastereoisomer. If the alkyl substitutent R2 was secondary, the diastereoselectivity decreased to 80:20. The reaction was shown to proceed stereoconvergently, and the relative product configuration was elucidated. The reaction outcome is explained by invoking a chiral propargylic cation as an intermediate, which is preferentially attacked by the nucleophile from one of its two diastereotopic faces. Density functional theory (DFT) calculations suggest a preferred conformation in which the group R2 is almost perpendicular to the plane defined by the three substituents at the cationic center, with the nucleophile approaching the electrophilic center opposite to R2. Transition states calculated for the reaction of allyltrimethylsilane with two representative cations support this hypothesis. Tertiary propargylic cations with a stereogenic center (-C* HXR2) in the α position were generated by ionization of the respective alcohol precursors with FSO3H in SO2ClF at -80 C. Nuclear magnetic resonance (NMR) spectra were obtained for five cations, and the chemical shifts could be unambiguously assigned. The preferred conformation of the cations as extracted from nuclear Overhauser experiments is in line with the preferred conformation responsible for the reaction of the secondary propargylic cations.

Steric effects and mechanism in the formation of hemi-acetals from aliphatic aldehydes

Some physical properties (pKa, log POW, boiling points) of hexanoic acid 1 (X = COOH) and its seven isomers 2, 3, 4, 5, 6, 7, 8 (X = COOH) are reported. Hexanal 1 (X = CHO) and its seven isomeric aldehydes 2, 3, 4, 5, 6, 7, 8 (X = CHO) are shown to equilibrate, in methanol solution, with their hemi-acetals. Logarithms of equilibrium constants correlate with values of Es for the isomeric C5H11 substituents, and with logs of relative rates for saponification of the corresponding methyl esters with ρ = 0.52, reflecting the reduced steric demand of hydrogen compared to oxygen in the quaternization of ester and aldehydic carbonyl groups. Rates of equilibration have also been measured in buffered methanol. For hexanal, with a 2:1 Et3N:AcOH buffer, the buffer-independent contribution is dominated by the methoxide catalysed pathway. Rates in this medium have been determined for isomers 1, 2, 3, 4, 5, 6, 7, 8 (X = CHO), and their logarithms do not correlate with logarithms of equilibrium constants for hemi-acetal formation or with substituent steric parameters derived from ester formation or saponification, indicating that the steric changes associated with full quaternization of the carbonyl group are not mirrored in the transition structures for hemi-acetal formation. It is suggested that transition states for hemi-acetal formation are relatively early so that steric interactions are effectively those between the nucleophile and ground state conformations of the aldehydes. A comparison of the entropies of hemi-acetal formation with entropies of activation has provided a basis for a suggested transition structure. Comparisons with acid chloride hydrolyses are made. Copyright 2013 John Wiley & Sons, Ltd. Logarithms of equilibrium constants for formation hemi-acetals of hexanal and its seven isomeric aldehydes correlate well with values of Es for the isomeric C5H11 substituents, and with logs of relative rates for saponification of the corresponding methyl esters. Logarithms of rate constants for hemi-acetal formation do not, indicating that the steric changes associated with full quaternization of the carbonyl group are not mirrored in the transition structures for hemi-acetal formation. The reasons for this are discussed. Copyright

High linear regioselectivity in the rhodium-catalyzed hydro(deuterio) formylation of 3,4,4-trimethylpent-1-ene: The role of β-hydride elimination

The regioselectivity in the hydroformylation reaction catalyzed by an unmodified Rh catalyst has been investigated for a number of α-methylsubstituted alk-1-enes (3-methylbut-1-ene MB1, 3-methylpent-1-ene MP1, 3,4-dimethylpent-1-ene DMP1, and 3,4,4-trimethylpent-1-ene TMP1) experimentally (at 20 °C and 100 atm CO/H2 total pressure) and theoretically at the B3P86/6-31G* level with Rh described by effective core potentials in the LanL2DZ valence basis set. For all substrates the formation of the linear aldehyde (L) with respect to the branched one (B) in a prevailing amount has been observed (L/B > 62/38); the L isomer was formed as the almost exclusive product in the case of TMP1 (L/B = 95/5). 2H NMR investigations of crude reaction mixtures, coming from analogous deuterioformylation experiments interrupted at partial substrate conversion, showed that in the case of TMP 1 only the branched alkyl-rhodium intermediate, precursor of the branched aldehyde, via β-hydride elimination mainly generates terminal deuterated olefins and, to a lesser extent, internal ones. The reversibility of the branched alkyl-Rh intermediates accounts for the high regioselectivity in favor of the linear aldehyde. Computational studies confirm the importance of the alkyl-Rh transition state (TS) stability to reproduce the experimental regioselectivity, or even to predict it, when the reaction is nonreversible (i.e. for MB1, MP1, and DMP1). In the case of TMP1, the free energy profiles for further reaction steps along branched and linear pathways have been examined to elucidate the origin of reaction reversibility. The TS for the alkyl migratory insertion onto the CO coordinated to rhodium, higher than that for the alkyl-Rh intermediate formation, explains the reason why in deuterioformylation experiments at partial conversion the monodeuterated terminal olefin TMP1-1-d1 is obtained. This occurs for one out of two most populated reactant conformers of TMP1, although for the Curtin-Hammett principle reactant populations are not particularly important. For the other, the reaction proceeds to the branched aldehyde. Only for a less populated reactant conformer the internal olefin is obtained. Conversely, along the linear pathway the CO addition and alkyl migratory insertion steps occur, respectively, in a practically spontaneous way and with very low TS in any case. Agostic interactions (using the QTAIM theory) and kinetic isotope effects have been evaluated and discussed. The examination of further reaction steps for DMP 1 allowed us to demonstrate that the reaction is nonreversible for that substrate, despite the similarity between DMP1 and TMP 1. The tert-butyl group exerts its steric hindrance mainly on the very first branched reaction steps, favoring an alkyl-Rh TS arrangement lower in free energy than the alkyl-Rh migratory insertion onto the coordinated CO. In part the branched material returns to the reactant complex, thus enriching the linear fraction.

BICYCLIC HETEROCYCLIC COMPOUND

In the prevention and/or treatment of a neuropsychiatric disease or a peripheral organ disease and the like, a pharmaceutical which comprises a compound having CRF antagonistic activity as an active ingredient is provided. A compound of a formula (I): wherein R1 represents a C3-10 branched alkyl group which may be substituted; R2 represents a hydrogen atom or a C1-4 alkyl group which may be substituted; R3 represents a C1-4 alkyl group which may be substituted or a halogen atom; R4 represents a C1-4 alkyl group which may be substituted; and ring 1 represents a cyclic group which has planarity and may have a substituent group, a salt thereof, an N-oxide thereof or a solvate thereof, or a prodrug thereof, is useful as a medicinal component having CRF antagonistic activity for the prevention and/or treatment of a neuropsychiatric disease, a peripheral organ disease and the like.

OH Radical Induced Oxidation of 2,3-Dimethylbutane in Air

The product distribution resulting from the OH induced oxidation of 2,3-dimethylbutane in air was measured and compared with predictions based on a general reaction mechanism.Relative rates derived for the abstraction of primary and tertiary hydrogen atoms by OH radicals from the parent compound are 17percent and 83percent, respectively.The branching ratio for the alcohol versus alkoxyl radical producing pathsways of the self-reaction of 2-propylperoxy radicals was determined to be (0.61 +/- 0.08):(0.39 +/- 0.08); the corresponding ratio for the self-reaction of primary 2,3-dimethylbutylperoxy radicals is (0.56 +/- 0.07): 0.44 +/- 0.07).Large amounts of 2,3-dimethyl-2-hydroperoxybutane and small amounts of 2,3-dimethyl-2-butanol were found, the latter as a product of the cross combination reactions of 2,3-dimethyl-2-butylperoxy with 2-propylperoxy and 2,3-dimethyl-1-butylperoxy radicals.Rate constants of 3.5 * 10-17 and 2 * 10-16 cm-3/(molecule s), respectively, were estimated for these reactions with the help of computer simulations.

KINETIC ANALYSIS OF ALKANE POLYCHLORINATION WITH MOLECULAR CHLORINE. CHLORINE ATOM/MONOCHLORIDE GEMINATE PAIRS AND THE EFFECT OF REACTIVE 'CAGE WALLS' ON THE COMPETITION BETWEEN MONOCHLORIDE ROTATION AND CHLORINE ATOM ESCAPE.

The free-radical chlorination of alkanes produces polychlorides even at low conversions. These are formed by reaction of chlorine atom/monochloride (or dichloride) geminate pairs. This process has been studied in detail in various solvent systems, and a kinetic scheme has been proposed. Deviations from this scheme have been rationalized as being due to competition between monochloride rotation and reaction of the chlorine atom with reactive molecules in the 'cage walls' surrounding the chlorine atom/chloride geminate pair. Analysis of the dichloride products supports the suggestion that monochloride rotation is not completely 'free' within the lifetime of the geminate pair.