6942-58-1

Usage

Uses

Used in Paint and Coating Industry:
2-hydroxyethyl isobutyrate is used as a solvent in paint and coating formulations for its ability to dissolve various components and improve the flow and application properties of the coatings.
Used in Adhesive and Sealant Production:
HEIB is used as a solvent in the production of adhesives and sealants, contributing to their adhesive strength and ease of application.
Used as a Flavoring Agent in Food Industry:
2-hydroxyethyl isobutyrate is used as a flavoring agent in food products, enhancing their taste and providing a sweet aroma.
Used as a Fragrance Ingredient in Cosmetics and Personal Care Industry:
HEIB is used as a fragrance ingredient in cosmetics and personal care products, adding a pleasant scent and improving the sensory experience of these products.

InChI:InChI=1/C6H12O3/c1-5(2)6(8)9-4-3-7/h5,7H,3-4H2,1-2H3

Upstream product

• 33498-32-7 2-(1-bromo-1-methyl-ethyl)-[1,3]dioxolane 
• 75-21-8 oxirane 
• 79-31-2 isobutyric Acid 
• 822-83-3 2-isopropyl-1,3-dioxolane 
• 66822-98-8 2-isopropyl-2-methoxy-1,3-dioxolane 
• 187737-37-7 propene 
• 201230-82-2 carbon monoxide 
• 107-21-1 ethylene glycol 
• 79-30-1 isobutyryl chloride 
• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 
• 78-84-2 isobutyraldehyde 
• 97-72-3 2-Methylpropionic anhydride 
• 111-29-5 1 ,5-pentanediol 
• 72592-05-3 3-isobutyroylamino-5-methylisoxazole 

Relevant academic research and scientific papers

Insights into the Molecular Recognition Process in Organocatalytic Chemoselective Monoacylation of 1,5-Pentanediol

Monoacylation of long-chain linear diols often encounters difficulties associated with unavoidable overacylation affording the diacylate. However, several C1- and C2-symmetrical pyrrolidinopyridine (PPY) catalysts were found to effectively promote the chemoselective monoacylation of 1,5-pentanediol. The effects of catalyst structure on the performance for the monoacylation were investigated. The amide carbonyl group(s) in the pyrrolidine ring in both C1- and C2-symmetrical catalysts was(were) suggested to play the key role in selective monoacylation. On the other hand, the indolyl NH group in the amide side chain of the catalysts was found to be critically important for further increasing the chemoselectivity of monoacylation only when the catalyst has a C2-symmetrical structure. The effects of the catalyst structure on the chemoselective monoacylation were elucidated by DFT calculations, and the origin of the precise molecular recognition for 1,5-pentanediol by the catalysts and transition state (TS) stabilization effects by these functionalities were disclosed.

Flavin-functionalized gold nanoparticles as an efficient catalyst for aerobic organic transformations

Monolayer-protected gold clusters functionalized with synthetic flavins were synthesized and their catalytic activity in aerobic organic transformations investigated. Gold nanoparticles with 5-ethyl-3-(8-thiooctyl)lumiflavinium perchlorate acts as an efficient catalyst for the aerobic oxidation of organic sulfides to the corresponding sulfoxides upon treatment with hydrazine at room temperature and under atmospheric pressure in oxygen. With a catalytic amount of gold nanoparticles with 3-(8-thiooctyl)lumiflavin, diimide reduction of various olefins can be performed with hydrazine at room temperature under atmospheric pressure in air with greater yields of product alkanes than with non-supported 3-methyllumiflavin catalyst under the same conditions. Kinetic studies revealed that the mono-layer-protected gold cluster-catalyzed reactions proceeded faster than those with non-supported catalysts over the full substrate concentration range for the hydrogenation of olefins and at lower substrate concentrations for sulfoxidation. This positive effect was rationalized by assuming a Michaelis-Menten-type mechanism in which the specific inclusion of substrates into the enzyme-like reaction cavities was a key factor in the high efficiency of the supported flavin catalysts.

Compositions, Synthesis, and Methods of Using Cycloalkylmethylamine Derivatives

The present invention provides novel cycloalkylmethylamine derivatives, and methods of preparing cycloalkylmethylamine derivatives. The present invention also provides methods of using cycloalkylmethylamine derivatives and compositions of cycloalkylmethylamine derivatives. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications and depression and depression related co-morbid indications.

Aerobic reduction of olefins by in situ generation of diimide with synthetic flavin catalysts

A versatile reducing agent, diimide, can be generated efficiently by the aerobic oxidation of hydrazine with neutral and cationic synthetic flavin catalysts 1 and 2. This technique provides a convenient and safe method for the aerobic reduction of olefins, which proceeds with 1 equiv of hydrazine under an atmosphere of O2 or air. The synthetic advantage over the conventional gas-based method has been illustrated through high hydrazine efficiency, easy and safe handling, and characteristic chemoselectivity. Vitamin B2 derivative 6 acts as a highly practical, robust catalyst for this purpose because of its high availability and recyclability. Association complexes of 1b with dendritic 2,5-bis(acylamino)pyridine 15 exhibit unprecedented catalytic activities, with the reduction of aromatic and hydroxy olefins proceeding significantly faster when a higher-generation dendrimer is used as a host pair for the association catalysts. Contrasting retardation is observed upon similar treatment of non-aromatic or non-hydroxy olefins with the dendrimer catalysts. Control experiments and kinetic studies revealed that these catalytic reactions include two independent, anaerobic and aerobic, processes for the generation of diimide from hydrazine. Positive and negative dendrimer effects on the catalytic reactions have been ascribed to the specific inclusion of hydrazine and olefinic substrates into the enzyme-like reaction cavities of the association complex catalysts. Copyright

Formulating a new basis for the treatment against botulinum neurotoxin intoxication: 3,4-Diaminopyridine prodrug design and characterization

Botulism is a disease characterized by neuromuscular paralysis and is produced from botulinum neurotoxins (BoNTs) found within the Gram positive bacterium Clostridium botulinum. This bacteria produces the most deadliest toxin known, with lethal doses as low as 1 ng/kg. Due to the relative ease of production and transport, the use of these agents as potential bioterrorist weapons has become of utmost concern. No small molecule therapies against BoNT intoxication have been approved to date. However, 3,4-diaminopyridine (3,4-DAP), a potent reversible inhibitor of voltage-gated potassium channels, is an effective cholinergic agonist used in the treatment of neuromuscular degenerative disorders that require cholinergic enhancement. 3,4-DAP has also been shown to facilitate recovery of neuromuscular action potential post botulinum intoxication by blocking K+ channels. Unfortunately, 3,4-DAP displays toxicity largely due to blood-brain-barrier (BBB) penetration. As a dual-action prodrug approach to cholinergic enhancement we have designed carbamate and amide conjugates of 3,4-DAP. The carbamate prodrug is intended to be a slowly reversible inhibitor of acetylcholinesterase (AChE) along the lines of the stigmines thereby allowing increased persistence of released acetylcholine within the synaptic cleft. As a secondary activity, cleavage of the carbamate prodrug by AChE will afford the localized release of 3,4-DAP, which in turn, will enhance the pre-synaptic release of additional acetylcholine. Being a competitive inhibitor with respect to acetylcholine, the activity of the prodrug will be greatest at the synaptic junctions most depleted of acetylcholine. Here we report upon the synthesis and biochemical characterization of three new classes of prodrugs intended to limit previously reported stability and toxicity issues. Of the prodrugs examined, compound 32, demonstrated the most clinically relevant half-life of 2.76 h, while selectively inhibiting AChE over butyrylcholinesterase-a plasma-based high activity esterase. Future in vivo studies could provide validation of prodrug 32 as a potential treatment against BoNT intoxication as well as other neuromuscular disorders.

Organocatalytic chemoselective monoacylation of 1,n-linear diols

Matters of length: Exclusive or predominant monoacylation of 1,n-linear diols took place in the presence of 1 when the chain length of linear diols was equal to or shorter than five carbon atoms. The chemoselectivity of acylation between 1,5-pentanediol (n=5) and 1,6-hexanediol (n=6) was 5.2, and that between 1,5-pentanediol and its monoacylate was 113. Copyright

Gold catalysis: In situ EXAFS study of homogeneous oxidative esterification

Gold complexes were prepared and investigated as catalysts for the oxidative esterification of aldehydes. Stabilisation by pyridine ligands gave good conversions and the in situ extended X-ray absorption fine structure (EXAFS) study of the reactions indicated that the reaction mixtures contained only mononuclear gold species. Thus, this is the first proof for a homogeneous gold-catalysed oxidation reaction ; the presence of nanoparticles could be excluded experimentally.

Experimental and DFT studies on competitive heterocyclic rearrangements. 3. A cascade isoxazole-1,2,4-oxadiazole-oxazole rearrangement

(Figure Presented) The thermal rearrangements of 3-acylamino-5- methylisoxazoles 1 have been investigated under basic and neutral conditions and interpreted with the support of computational data. The density functional theory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement of isoxazoles 1 showed that the Boulton-Katritzky (BK) rearrangement, producing the less stable 3-acetonyl-1,2,4-oxadiazoles 5, is a much more favored process than either the migration-nucleophilic attack-cyclization (MNAC) or the ring contraction-ring expansion (RCRE). In turn, an increase in reaction temperature will promote the MNAC of oxadiazoles 5, producing the more stable 2-acylaminooxazoles 8. The thermal rearrangement of 3-acylaminoisoxazoles 1 into oxazoles 8 can therefore be interpreted in terms of a cascade BK-MNAC rearrangement involving 3-acetonyl-1,2,4-oxadiazoles 5 as ancillary intermediates.

One-pot o-nitrobenzenesulfonylhydrazide (NBSH) formation-diimide alkene reduction protocol

A one-pot protocol for the formation of 2-nitrobenzenesulfonylhydrazide (NBSH) from commercial reagents and subsequent alkene reduction is presented. The transformation is operationally simple and generally efficient for effecting diimide alkene reductions. A range of 16 substrates have been reduced, highlighting the unique chemoselectivity of diimide as a reduction system.

Flavin-catalyzed generation of diimide: An environmentally friendly method for the aerobic hydrogenation of olefins

The first green and practical method for "aerobic hydrogenation" involving the use of hydrazine and an organocatalyst is described. Olefins can be hydrogenated by treatment with hydrazine in the presence of a 5-ethyl-3-methyllumiflavinium perchlorate (FlEt+·ClO4-) catalyst under O2 atmosphere to give the corresponding hydrogenated products in excellent yields along with environmentally benign water and molecular nitrogen as the only waste products. Copyright