151-00-8

Usage

Uses

Used in Organic Synthesis:
Isobutyraldehyde oxime is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of a wide range of organic compounds.
Used in Pesticide Production:
Isobutyraldehyde oxime is used as a key intermediate in the production of pesticides, where it plays a crucial role in the synthesis of active ingredients that help control and manage pests in agriculture.
Used in Pharmaceutical Industry:
Isobutyraldehyde oxime is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and medications that address various health conditions.
Used in Corrosion Inhibition:
Isobutyraldehyde oxime has been studied for its potential as a corrosion inhibitor, where it can be used to protect metal surfaces from corrosion, extending the lifespan of equipment and structures in various industries.
Used as a Precursor for Synthesis of Other Compounds:
Isobutyraldehyde oxime serves as a versatile precursor in the synthesis of other compounds, enabling the creation of new chemical entities with potential applications in various fields, including materials science, chemical research, and specialty chemicals.

InChI:InChI=1/C4H9NO/c1-4(2)3-5-6/h3-4,6H,1-2H3/b5-3+

Upstream product

• 625-74-1 1-nitroisobutane 
• 108725-89-9 1-hydroxy-2-methyl-propane-1-sulfonic acid 
• 78-84-2 isobutyraldehyde 
• 82517-57-5 1-nitroso-1-isobutylhydrazine 
• 488-05-1 3-methyl-1-(3-methylfuran-2-yl)butan-1-one 
• 60-29-7 diethyl ether 
• 109-95-5 ethyl nitrite 
• 1606-30-0 1-Nitro-2-methyl-1-propen 
• 64-19-7 acetic acid 

Downstream Products

• 65655-87-0 2-Isopropyl-3-hydroxy-4-oxo-tetrahydrothiazol 
• 684-88-8 2-methylpropanehydroxamoyl chloride 
• 684-88-8 (1Z)-N-hydroxy-2-methyl-propanimidoyl chloride 
• 61858-79-5 (3-isopropyl-isoxazol-5-ylmethyl)-triphenyl-phosphonium; bromide 
• 713-77-9 S-p-Tolyl-isobutyrothiohydroximat 
• 90653-69-3 3-benzoyl-5-isopropyl-1,2,4-oxadiazole 
• 78-82-0 Isobutyronitrile 
• 87074-56-4 1-(3-Isopropyl-4,5-dihydro-isoxazol-5-yl)-ethanone 
• 78-84-2 isobutyraldehyde 
• 64988-71-2 5-(chloromethyl)-3-isopropylisoxazole 
• 590-86-3 isovaleraldehyde 
• 79-31-2 isobutyric Acid 
• 162218-92-0 methyl 3-isopropyl-4,5-dihydroisoxazole-5-carboxylate 
• 1346238-46-7 3-isopropyl-5-(4-methoxyphenyl)isoxazole 

Relevant academic research and scientific papers

Isothiocyanates and Glucosinolates from Sisymbrium officinale (L.) Scop. (“the Singers’ Plant”): Isolation and in vitro assays on the somatosensory and pain receptor TRPA1 channel

Sisymbrium officinale (L.) Scop. is a wild common plant of the Brassicaceae family. It is known as “the singers’ plant” for its traditional use in treating aphonia and vocal disability. Despite its wide use in herbal preparations, the molecular mechanism of action of S. officinale extracts is not known. The plant is rich in glucosinolates and isothiocyanates, which are supposed to be its active compounds. Some members of this family, in particular allylisothiocyanate, are strong agonists of the transient receptor potential ankyrin 1 (TRPA1) channel, which is involved in the somatosensory perception of pungency as well as in the nociception pathway of inflammatory pain. This study aims to isolate the glucosinolates and isothiocianates from fresh S. officinale to identify the major components and test their activity in in vitro assays with a cloned TRPA1 channel. Samples of cultivated S. officinale have been extracted and the active compounds isolated by column chromatography, HPLC and PTLC. The main components glucoputranjivin, isopropylisothiocyanate and 2-buthylisothiocianate have been tested on TRPA1. The glucosinolates glucoputranjivin and sinigrin turned out to be inactive, while isopropylisothiocyanate and 2-buthylisothiocyanate are potent agonists of TRPA1, with an EC50 in the range of the high potency natural agonists identified so far for this somatosensory channel.

Process development and multikilogram syntheses of XL228 utilizing a regioselective isoxazole formation and a selective SNAr reaction to a pyrimidine core

Route scouting, process development, and multikilogram syntheses of an IGF-1R/Src/Bcr-Abl inihibitor are reported. Key aspects of the developed route are a regioselective [3 + 2] isoxazole formation on a pyrimidine core and a selective SNAr addition of an aryl amine to a symmetrical dichloro substituted pyrimidine. The route contains six synthetic steps and was demonstrated twice on scale, delivering 4.6 and 11.2 kg (25% and 16% overall yield), for Phase I clinical studies.

Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes

Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer of aryl alkyl ketoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Z isomer of aryl alkyl oximes, a class of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides, and amides having a single configuration.

COMPOUNS, COMPOSITIONS AND METHODS OF USE

Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.

IMIDAZOPYRROLOPYRIDINE AS INHIBITORS OF THE JAK FAMILY OF KINASES

2-((1r,4r)-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)acetonitrile compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions mediated by JAK, such as inflammatory bowel disease.

An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides

A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).

1,3-Dipolar cycloaddition of uracil derivatives with nitrile oxides: Synthesis of [1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione derivatives

An efficient method of synthesizing bicyclic fused [1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione derivatives was developed through a [3 + 2] cycloaddition of uracil derivatives and nitrile oxides. In the one step reaction, C[sbnd]N and C[sbnd]O bonds were constructed, the target compounds were efficiently obtained in good yields. The method represents a valuable way to obtain highly functional fused bicyclic heterocycle derivatives in a simple, rapid and practical manner. The method fusing bicyclic heterocycles can be applied for modification of uracil analogues that may have potential biological activities.

PIPERIDINYL-SUBSTITUTED LACTAMS AS GPR119 MODULATORS

Compounds of Formula (I) and pharmaceutically acceptable salts thereof in which X1, X2, X3, L, R3, R4, R5, R7 and n have the meanings given in the specification, are modulators of GPR119 and are useful in the treatment or prevention of diseases such as such as, but not limited to, type 2 diabetes, diabetic complications, symptoms of diabetes, metabolic syndrome, obesity, dyslipidemia, and related conditions.

Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes

The dipolar cycloadditions of ortho-nitrophenyl alkynes with aryl nitrile oxides has been demonstrated. A range of substituents are tolerated on the alkyne. These reactions proceed with excellent levels of regioselectivity. Subsequent functionalization of the isoxazole scaffold has been demonstrated.

Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties

An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoro- and trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt3 as catalytic basic agent to provide the corresponding product in 28-94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine- and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2,4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells.