33279-01-5

Basic information

• Product Name: 3-OXO-PENTANENITRILE
• Synonyms: 3-OXO-PENTANENITRILE;3-OXOPENTANONITRILE;Propionylacetonitrile;Propanoylacetonitrile, 1-Cyanobutan-2-one;cyanoMethyl ethyl ketone;Pentanenitrile, 3-oxo-
• CAS NO: 33279-01-5
• Molecular Formula: C₅H₇NO
• Molecular Weight: 97.12
• Mol File: 33279-01-5.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 30°C
• Flash Point: 42.2°C
• Appearance: /
• Density: 0.956g/cm³
• Vapor Pressure: 4.713mmHg at 25°C
• Refractive Index: 1.41
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.37±0.10(Predicted)
• CAS DataBase Reference: 3-OXO-PENTANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXO-PENTANENITRILE(33279-01-5)
• EPA Substance Registry System: 3-OXO-PENTANENITRILE(33279-01-5)

Safety Data

• Hazard Codes: T
• RIDADR: UN3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 33279-01-5(Hazardous Substances Data)

Usage

Uses

A facile procedure for the high-yielding acylation of nitrile anions with unactivated esters to provide β-?keto nitriles (Propionylacetonitrile) is reported.

InChI:InChI=1/C5H7NO/c1-2-5(7)3-4-6/h2-3H2,1H3

Upstream product

• 105-37-3 Ethyl propionate 
• 75-05-8 acetonitrile 
• 554-12-1 propanoic acid methyl ester 
• 79-03-8 propionyl chloride 
• 13284-42-9 2-pentenenitrile 
• 105-56-6 ethyl 2-cyanoacetate 
• 90087-51-7 2-Cyano-3-oxo-pentanoic acid ethyl ester 
• 616-27-3 1-chlorobutan-2-one 
• 151-50-8 potassium cyanide 

Downstream Products

• 64231-10-3 4-ethyl-7-hydroxy-2H-1-benzopyran-2-one 
• 1207895-42-8 (E)-2-benzylidene-3-oxopentanenitrile 
• 1226191-26-9 3-ethyl-1-(p-tolyl)-1H-pyrazol-5-amine 
• 4949-44-4 ethyl propanoylacetate 
• 1202352-59-7 3-ethyl-4-(4-methoxyphenyl)-1H-pyrazol-5-amine 
• 1031699-69-0 3-ethyl-4-(4-fluorophenyl)-1H-pyrazol-5-amine 
• 77186-59-5 3-oxo-2-(3-(trifluoromethyl)phenyl)pentanenitrile 

Relevant articles and documents

Synthesis and anticonvulsant activity of enaminones. 4. Investigations on isoxazole derivatives

Due to the exceptional anticonvulsant activity displayed by substituted aniline enaminones, related pyridine derivatives and phenothiazines synthesised in our laboratories, the further investigation of various aromatic heterocycles was undertaken. Condensation of cyclic 1,3-diketo esters with 3-, and 5-aminoisoxazole derivatives led to a series of potent anti-maximal electroshock (MES) analogues, three of which occurred in the 3-amino series: ethyl ester (10), orally (po) active in rats [ED50 68.9 mg kg-1, TD50>500 mg kg-1, protective index (PI=TD50/ED50)>49.6]; methyl ester (9), ED50 68.9 mg kg-1 intraperitoneally (ip) in mice, TD50>500 mg kg-1, PI>7.3, and tert-butyl ester (8), ED50 28.1 mg kg-1 po in rats, TD50>500 mg kg-1, PI>17.8. Sodium channel binding studies, as well as evaluations against pentylenetetrazol, bicuculline, and picrotoxin on isoxazole 10 were all negative, leading to an unknown mechanism of action. X-ray diffraction patterns of a representative of the 3-amino series (isoxazoles 6-11) unequivocally display the existence of intramolecular hydrogen bonding of the nitrogen to the vinylic proton in the cyclohexene ring, providing a pseudo three ring structure which was also shown previously with the vinylic benzamides. Physicochemical-permeability across the BBB suggested an efflux mechanism for the previously synthesised aniline enaminones, but not with isoxazole 10.

Identification of TRD-35 as Potent and Selective DRAK2 Inhibitor

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Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.