71591-87-2

Basic information

• Product Name: 2,4-Pentanedione, 3-(aminomethylene)- (6CI,7CI,9CI)
• Synonyms: 2,4-Pentanedione, 3-(aminomethylene)- (6CI,7CI,9CI);3-(AMinoMethylene)pentane-2,4-dione;3-(aminomethylidene)pentane-2,4-dione
• CAS NO: 71591-87-2
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14116
• Product Categories: ACETYLGROUP
• Mol File: 71591-87-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 142 °C
• Boiling Point: 276.5°C at 760 mmHg
• Flash Point: 121°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 0.00478mmHg at 25°C
• Refractive Index: 1.472
• PKA: 3.06±0.70(Predicted)
• CAS DataBase Reference: 2,4-Pentanedione, 3-(aminomethylene)- (6CI,7CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pentanedione, 3-(aminomethylene)- (6CI,7CI,9CI)(71591-87-2)
• EPA Substance Registry System: 2,4-Pentanedione, 3-(aminomethylene)- (6CI,7CI,9CI)(71591-87-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 71591-87-2(Hazardous Substances Data)

Usage

General Description

2,4-Pentanedione, 3-(aminomethylene)- (6CI,7CI,9CI) is a chemical compound with the molecular formula C7H11NO2. It is also known as 3-(aminomethylene)-2,4-pentanedione and is commonly used as a reagent in organic synthesis. The compound has potential applications as a building block for the synthesis of various pharmaceuticals and agrochemicals. It is a ketone with an aminomethylene group attached to the third carbon atom, and its structure makes it reactive towards nucleophiles. The compound has a wide range of chemical and industrial applications, and its properties make it a versatile and valuable tool in organic chemistry.

InChI:InChI=1/C6H9NO2/c1-4(8)6(3-7)5(2)9/h3H,7H2,1-2H3

Upstream product

• 33884-41-2 ethoxylideneacetylacetone 
• 290-87-9 1,3,5-Triazine 
• 123-54-6 acetylacetone 
• 18856-72-9 3-dimethylaminomethylenepentane-2,4-dione 
• 100596-16-5 3-(1,3-dithian-2-yl)-pentane-2,4-dione 
• 16690-08-7 3-formyl-2,4-dioxopentane 
• 289-96-3 1,2,3-triazine 
• 71043-35-1 3-methoxymethylenepentane-2,4-dione 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 7664-41-7 ammonia 
• 42397-39-7 Phenyl-methyl-sulfilimin 

Downstream Products

• 100393-56-4 3-(benzoylamino-methylene)-pentane-2,4-dione 
• 21686-05-5 1-(1,5-dimethyl-1H-pyrazol-4-yl)ethan-1-one 
• 66373-27-1 acetyl-5 methyl-4 phenyl-2 pyrimidine 

Relevant articles and documents

Conformational studies of 3-aminomethylene-2,4-pentanedione using vibrational and NMR spectra, and ab initio calculations

The IR, Raman and NMR spectra of 3-aminomethylene-2,4-pentanedione (AMP) H2N{single bond}CH{double bond, long}C(COCH3)2 were measured. According to the NMR spectra in chloroform and more polar DMSO at room temperature, the sample exists as single entity. On the other hand vibrational spectra revealed that in less polar solutions AMP exists as two conformers with EZ or ZZ orientation of acetyl groups whereas in more polar solvent only one EZ conformer is observed. Such interpretation was confirmed also by the temperature-dependent measurements of IR spectra in chloroform. The observed IR and Raman bands were compared with harmonic vibrational frequencies, calculated using ab initio MP2 and B3LYP density functional methods in 6-31G** basis set, and assigned on the basis of potential energy distribution. In addition, the geometries and relative energies of possible conformers of AMP were also evaluated at the same levels of theory and compared with the data from X-ray analysis which revealed that AMP exists in solid state as EZ conformer. The influence of environment polarity on this conformational equilibrium is discussed with respect to the SCRF solvent effect calculations using PCM, IPCM and ONSAGER models.

Vilsmeier reaction of 3-aminopropenamides: One-pot synthesis of pyrimidin-4(3 H)-ones

A facile one-pot synthesis of pyrimidin-4(3H)-ones was developed via reactions of a series of readily available 3-aminopropenamides with varied Vilsmeier reagents, and a mechanism involving sequential halogenation, formylation, and intramolecular nucleoph

New reactivity of nitropyrimidinone: Ring transformation and N-C transfer reactions

Nitropyrimidinone 1 revealed new reactivity upon treatment with active methylene compounds 2 under basic conditions. The N1-C2-C3-C4 moiety of 1 combined with two carbon units of 2 affording polyfunctionalized pyridones 4, which was hitherto unknown ring transformation. On the other hand, the N1-C2 moiety of 1 was transferred to the methylene group of 2 giving functionalized enamines 3. It was also possible to modify the amino group in 3a by reactions with primary amines. Enamines 3 reacted with hydrazines, and leading to functionalized pyrazoles 7 quantitatively. The ratios of regioisomeric pyrazoles 7/8 were moderately controlled by use of sterically hindered enamines 3h, 3k and 31. Furthermore, enamine 3a was readily converted to 1,4-diazepines 9 having a functional group at the 6-position.