33884-41-2

Basic information

• Product Name: 3-(ETHOXYMETHYLENE)-2,4-PENTANEDIONE
• Synonyms: AKOS MSC-0742;3-(ETHOXYMETHYLENE)-2,4-PENTANEDIONE;3-(ETHOXYMETHYLENE)ACETYLACETONE;3-ETHOXY METHYLENE PENTANE-2,4-DIONE;3-Ethoxymethylene-2,4-pentanedione, 98+%;3-(Ethoxymethylene)-2,4-pentanedione,97%;3-Ethoxymethylene-2,4-pentandione;3-(EthoxyMethylene)-2,4-pentanedione, 97% 1GR
• CAS NO: 33884-41-2
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.18
• Mol File: 33884-41-2.mol

Chemical Properties

• Boiling Point: 140-142 °C (16 mmHg)
• Flash Point: 140-142°C/15mm
• Appearance: Clear yellow liquid
• Density: 1.01 g/cm³
• Vapor Pressure: 0.00094mmHg at 25°C
• Refractive Index: 1.483-1.485
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(ETHOXYMETHYLENE)-2,4-PENTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(ETHOXYMETHYLENE)-2,4-PENTANEDIONE(33884-41-2)
• EPA Substance Registry System: 3-(ETHOXYMETHYLENE)-2,4-PENTANEDIONE(33884-41-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 33884-41-2(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

InChI:InChI=1/C8H12O3/c1-4-11-5-8(6(2)9)7(3)10/h5H,4H2,1-3H3

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 123-54-6 acetylacetone 

Downstream Products

• 108994-21-4 3-(2-nitro-2-phenyl-ethylidene)-pentane-2,4-dione 
• 112599-50-5 N³,N⁵-bis-(2-acetyl-3-oxo-but-1-enyl)-1-phenyl-1H-[1,2,4]triazole-3,5-diyldiamine 
• 109516-00-9 6-acetyl-5-methyl-1-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione 
• 124135-54-2 6-[1-(2,6-dioxo-3-phenyl-1,2,3,6-tetrahydro-pyrimidin-4-ylimino)-ethyl]-5-methyl-1-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione 
• 55933-85-2 acetyl-5 dimethyl-2,4 pyrimidine 
• 66373-25-9 acetyl-5 amino-2 methyl-4 pyrimidine 
• 66373-27-1 acetyl-5 methyl-4 phenyl-2 pyrimidine 
• 71591-87-2 3-(aminomethylene)pentane-2,4-dione 
• 105224-04-2 1-(3-methyl-1H-pyrazol-4-yl)ethanone 
• 1522-25-4 4-hydroxy-3-methylpent-3-en-2-one 
• 109655-05-2 6-acetyl-3,5-dimethyl-1-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione 
• 110152-83-5 6-acetyl-1-(4-ethoxy-phenyl)-5-methyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione 
• 100393-56-4 3-(benzoylamino-methylene)-pentane-2,4-dione 
• 70450-87-2 3-((phenylamino)methylene)pentane-2,4-dione 

Relevant articles and documents

Synthesis and properties of water-soluble 2-aminomethylidene derivatives of 1,3-dicarbonyl compounds

A series of [(2-dimethylamino)ethylamino]methylidene-1,3-dicarbonyl compounds was synthesized for the first time starting from the corresponding 2-ethoxymethylidene derivatives and N,N-dimethylethylenediamine. It was shown that further alkylation of aminomethylidene derivatives with methyl iodide occurs regioselectively at the tertiary nitrogen atom. Quaternization products obtained exhibit high corrosion inhibition of mild steel in hydrochloric acid medium.

Development of DHQ-based chemical biology probe to profile cellular targets for HBV

Chronic hepatitis B virus (HBV) infection has been a serious public health burden worldwide. Current anti-HBV therapies could not eliminate HBV ultimately. Considering the characteristics of HBV, it is impossible to be entirely cured based on current therapies. Therefore, it is urgently needed to develop novel therapeutic agents with new mechanism of action. The dihydroquinolizinone (DHQ) derivatives exhibited potent anti-HBV activity by decreasing HBV DNA and HBsAg level in an obscure mechanism of action. In this study, we have optimized the DHQ scaffold, developed the photoaffinity probe, with which to identify potential binding proteins.

Toward Continuous-Flow Synthesis of Biologically Interesting Pyrazole Derivatives

A two-step continuous-flow synthesis of substituted pyrazole derivatives has been developed via the formation of vinylidene keto esters as key intermediates. Heterogeneous Ni2+-montmorillonite was found to be an efficient catalyst for orthoester condensation of 1,3-dicarbonyls under flow conditions. The intermediate reacted with methylhydrazine to afford pyrazole derivatives, for which suitable selection of a solvent played a key role in achieving high yields and excellent regioselectivities of the desired products. An application of this protocol has been demonstrated by the synthesis of a key intermediate for biologically active pyrazoles such as Bixafen. (Figure presented.).

PYRIDINONE- AND PYRIDAZINONE-BASED COMPOUNDS AND MEDICAL USES THEREOF

The various examples presented herein are directed to compounds of the formula A-L1-Het1-L2-Cy1 or a pharmaceutical acceptable salt, polymorph, prodrug, solvate or clathrate thereof, wherein: A is cycloalkyl, aryl, arylalkyl or heterocyclyl; Het1 is heterocyclyl containing at least two heteroatoms; Cy1 is a heterocyclyl; L1 is a bond, alkyl, alkenyl or alkynyl linker; L2 is an acyl or alkyl linker; and A and Cy1 are different. The compounds are useful in the treatment of fibrotic diseases, abnormal vascular leak and pathological angiogenesis.

N → N acyl group migration in N-acylpyrazoles: Isomerization of 1,4-diacyl-5-methyl-1H-pyrazoles to 1,4-diacyl-3-methyl-1H-pyrazoles

1,4-Diacyl-5-methyl-1H-pyrazoles on heating in toluene undergo isomerization to 1,4-diacyl-3-methyl-1H-pyrazoles via intermolecular N → N acyl group migration. 1,4,5-Trisubstituted pyrazoles obtained by reaction of 2-ethoxymethylidene derivatives of 1,3-diketones with 1,3-benzothiazol-2-ylhydrazine or phenylhydrazine failed to isomerize to 1,3,4-trisubstituted pyrazoles.

SUBSTITUTED PYRIMIDINE COMPOUNDS AS mPGES-1 INHIBITORS

The present disclosure is directed to substituted pyrimidine compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and a

TETRAHYDROPYRAZOLOPYRIMIDINE COMPOUNDS

Embodiments of the disclosure relate to tetrahydropyrazolopyrimidine compounds that act as antagonists or inhibitors for Toll-like receptors 7 and/or 8, and their use in pharmaceutical compositions effective for treatment of systemic lupus erythematosus (SLE) and lupus nephritis

NMR spectroscopic data of some 1-alkoxy-2,2-di(carbonyl, carboxyl, cyano)-substituted ethylenes

The 1H-13C NMR shifts as well as 1H and 13C coupling constants of 14 alkoxymethylene malonic acid and acetoacetic acid derivatives and two alkoxymethylene acetylacetones are reported. The 17O NMR spectra have been recorded for six of them. The long-range coupling 3J(H-C=C-CR) has been used for determining the stereochemistry of the double bond. Copyright

Solvent-free synthesis of quinolone derivatives

Quinolones can be prepared in a three step procedure from triethylorthoformate and activated methylene derivatives leading to alkoxymethylenemalonates followed by reaction with aromatic amines and finally a cyclization. All the reactions were carried out under solvent-free conditions possibly under microwave activation with benefits for the first step.

Synthesis and solid-state polymerization of 5-(2-methylthio4-methylpyrimidin-5-yl)penta-2,4-diyn-l-ol and of several of its derivatives

5-(2-Methylthio-4-methylpyrimidin-5-yl)penta-2,4-diyn-1-ol was synthesized by asymmetric coupling, and the corresponding diacetylene monomers were also prepared in good yields. These monomers could be dissolved in common organic solvents. The monomers can be polymerized in the solid state using heat, light or y-radiation. In addition, micro- and macroscopic third-order susceptibilities were measured by the degenerate four-wave mixing (DFWM) method for the yielded polymers. The Royal Society of Chemistry 2000.