52200-09-6

Basic information

• Product Name: 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE
• Synonyms: 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE;2-BENZOYL-3-(DIMETHYLAMINO)ACRYLONITRILE;(E)-2-BENZOYL-3-(DIMETHYLAMINO)-2-PROPENENITRILE;2-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrile 95%;alpha-[(Dimethylamino)methylene]-beta-oxobenzenepropanenitrile;2-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrile95%
• CAS NO: 52200-09-6
• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200.24
• Mol File: 52200-09-6.mol

Chemical Properties

• Melting Point: 128-129℃
• Boiling Point: 396℃
• Flash Point: 193℃
• Appearance: /
• Density: 1.106
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE(52200-09-6)
• EPA Substance Registry System: 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE(52200-09-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 52200-09-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE is used as a key intermediate in organic synthesis for the creation of complex organic molecules. Its structural features allow for versatile chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE is utilized as a building block for the development of new drugs. Its unique properties make it suitable for the design of molecules with specific therapeutic targets, potentially leading to the discovery of innovative treatments for various diseases.
Used in Medicinal Chemistry:
2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE is employed in medicinal chemistry for the exploration of its bioactivity. Its structural elements can be manipulated to probe its interactions with biological targets, offering insights into its potential as a therapeutic agent.
Used in Pharmacology:
In pharmacology, 2-[(DIMETHYLAMINO)METHYLENE]-3-OXO-3-PHENYLPROPANENITRILE may be used to study its pharmacological properties, such as absorption, distribution, metabolism, and excretion, as well as its potential effects on biological systems. This research can contribute to a better understanding of its therapeutic potential and safety profile.

InChI:InChI=1/C12H12N2O/c1-14(2)9-11(8-13)12(15)10-6-4-3-5-7-10/h3-7,9H,1-2H3

Upstream product

• 614-16-4 Benzoylacetonitrile 
• 20353-93-9 Gold's reagent 
• 758-16-7 N,N-dimethylthioformamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 532-27-4 1-chloroacetophenone 
• 7145-48-4 Benzoylacetaldehyde ω-oxime 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 210235-65-7 1-Allyl-3-((E)-2-cyano-3-oxo-3-phenyl-propenyl)-thiourea 
• 210235-54-4 1-((E)-2-Cyano-3-oxo-3-phenyl-propenyl)-3-ethyl-urea 
• 210235-57-7 1-((E)-2-Cyano-3-oxo-3-phenyl-propenyl)-3-phenyl-urea 
• 210235-56-6 1-Benzyl-3-((E)-2-cyano-3-oxo-3-phenyl-propenyl)-urea 
• 210235-59-9 1-(2-Chloro-phenyl)-3-((E)-2-cyano-3-oxo-3-phenyl-propenyl)-urea 
• 210235-60-2 1-(3-Chloro-phenyl)-3-((E)-2-cyano-3-oxo-3-phenyl-propenyl)-urea 
• 210235-63-5 1-((E)-2-Cyano-3-oxo-3-phenyl-propenyl)-3-(3-trifluoromethyl-phenyl)-urea 
• 210235-64-6 1-((E)-2-Cyano-3-oxo-3-phenyl-propenyl)-3-methyl-thiourea 
• 210235-53-3 1-((E)-2-Cyano-3-oxo-3-phenyl-propenyl)-3-methyl-urea 
• 210235-62-4 1-(4-Chloro-phenyl)-3-((E)-2-cyano-3-oxo-3-phenyl-propenyl)-urea 
• 931114-31-7 (5-amino-1H-pyrazol-4-yl)(phenyl)methanone 
• 264927-84-6 2-amino-5-cyano-4-phenylpyrimidine 

Relevant articles and documents

Cyanoacetophenone as a synthon for 1,4,5-substituted pyrazoles

An improved synthesis of cyanoacetophenone is described. Cyanoacetophenone was reacted with dimethylformamide-dimethylacetal and diphenylformamidine to give 1-dimethylamino-3-oxo-3-phenyl-1-propene-2-carbonitrile and 1-anilinomethylene-3-oxo-3-phenyl-1-propene-2-carbonitrile. Reaction of 1-dimethylamino-3-oxo-3-phenyl-1-propene-2-carbonitrile with hydrazines gave either 1-substituted 5-amino-4-benzoylpyrazoles or (1-substituted) 4-cyano-5-phenylpyrazoles. Treatment of 1-anilinomethylene-3-oxo-3-phenyl-1-propene-2-carbonitrile with phenylhydrazine also yielded 5-amino-4-benzoyl-1-phenylpyrazole, whereas reaction with unsubstituted hydrazine afforded 4-cyano-5-phenylpyrazole.

Studies with functionally substituted enamines: Synthesis of 2-aroyl-3-dimethylamino-2-propenenitrile and their reactivity toward nitrogen nucleophiles

A facile and efficient synthesis of 2-substituted 3-dimethylamino-2-propenenitrile 4a-c is described. Reaction of 4a-c with hydrazine hydrate afforded 3-substituted-1H-4-pyrazole carbonitrile 9a-c. Compounds 4a-c reacted with 5-methyl-1H-pyrazol-3-amine to give 7-substituted pyrazolo[1,5-a]pyrimidine-6-carbonitrile 12a-c and 2-substituted 5-aminopyrazolo[1,5-a]pyrimidine 16a,b, and with 1H-benzo[d]imidazol-2-amine to give 3-substituted 2-aminobenzo[4,5]imidazo[1,2-a]pyrimidine 19a,b and 4-substituted benzo[4,5]imidazo[1,2-a]pyrimidine 3-carbonitrile 21c. The structures of compounds obtained were deduced based on 1HNMR, HMBC-15N and NOE difference experiments.

Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo[1,5-a]pyrimidines as novel larotrectinib analogs

A series of 2-phenyl-7-(aryl)pyrazolo[1,5-a]pyrimidine-3-carbonitriles 11a–j and 2-phenyl-7-(aryl)pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitriles 16a–c was synthesized by the reaction of 5-amino-3-phenyl-1H-pyrazole-4-carbonitrile (5) with 3-(dimethylamino)

New trisubstituted cyanopyrazoles and cyanoscorpionates

New syntheses are reported to give pyrazoles with cyano substituents at the 4-position of the pyrazole ring and ethyl or isopropyl substituents at the 3-position, as well as pyrazoles with cyano substituents at the 4-position and alkyl/aryl/bromo substituents at both the 3- and 5-positions. Synthesis of scorpionates using tetradecane as a high-boiling solvent has been shown to be more efficient than the melt method and has led to new scorpionates using the newly synthesized pyrazoles. An unexpected complex is isolated in which the Ni(cyclam)2+moiety crystallizes with two cyanoscorpionates as counterions, without binding of the scorpionate ligands to the Ni atom.

4-Aryl-5-cyano-2-aminopyrimidines as VEGF-R2 inhibitors: Synthesis and biological evaluation

A novel series of 4-aryl-5-cyano-2-aminopyrimidines were synthesized and found to have potent VEGF-R2 kinase inhibitory activity. Structure-activity relationships were investigated and compound 14a was shown to be efficacious in a mouse model of corneal neovascularization.

Synthesis of some new 6,8-disubstituted 7,8-dihydropyrimido[2,3:4,3] pyrazolo[1,5-a]pyrimidines and 6,7,8-trisubstituted pyrimido[2,3:4,3]pyrazolo[1, 5-a]pyrimidine derivatives

Cyclization of 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine 4 with excess of 85% hydrazine hydrate afforded the 3-amino-4-methyl-6- phenylpyrazolo[3,4-d]pyrimidine 5, which can react with appropriate Mannich base derivatives 13a-c and chalcones 27a,b to yield the corresponding 6,8-disubstituted 7,8-dihydropyrimido[2,3:4,3]pyrazolo[1,5-a]pyrimidines 15a-c and 30a,b, respectively. On the other hand, the 6,7,8-trisubstituted pyrimido[2,3:4,3]pyrazolo[1,5-a]pyrimidine derivatives 8a-g, 20a-e, 36 and 38 were obtained by treatment of compound 5 with appropriate 1,3-diketones 6a-g, 3-dimethylamino-1-(substituted)prop-2-enones 18a-e, 3-aminocrotononitrile 3, and ethoxymethylenemalononitrile 37 under acidic condition, respectively.

4-Substituted 1,5-diarylpyrazole, analogues of celecoxib: Synthesis and preliminary evaluation of biological properties

A number of 5-aryl-1-[4-(methylsulfonyl)-phenyl]-1H-pyrazoles and 4-(5-aryl-1H-pyrazol-1-yl)benzenesulfonamides 3, 4, 5, 6, analogues of the COX-2 selective inhibitor celecoxib (celebrex), were synthesized. In order to verify the effects on the biological properties of certain substituents put on position 4 of the pyrazole nucleus, some of these compounds were screened in vivo for their anti-inflammatory and analgesic activities. Moreover, sodium salts of carboxylic acids 4 were tested in vitro for their platelet anti-aggregating properties. The results of these preliminary biological assays showed that new derivatives are not endowed with improved anti-inflammatory and analgesic properties, in comparison with celecoxib. In addition, docking studies were carried out on the most significative compounds to evaluate their interaction mode at the active site of both COX-1 and COX-2. Some remarks about the SAR of this class of COX-inhibitors are drown out.

Silver(I) Ion Mediatied Desulfurization-Condensation of Thiocarbonyl Compounds with Several Nucleophiles

The desulfurization-condensation reaction was investigated in the presence of silver(I) salt for several kinds of thiocarbonyl compounds with nucleophiles.Such thiocarbonyl compounds as 4,4'-bis(dimethylamino)thiobenzophenone, ethylene trithiocarbonate, and N-(thiobenzoyl)morpholine react with malononitrile or other active methylene compounds in the presence of silver trifluoroacetate to afford the corresponding olefinic compounds together with silver sulfide.This reaction of thiocarbonyl compounds with some other nucleophiles such as aniline derivatives and ethylene glycol, has also afforded imines and 1,3-dioxolane derivatives.

FORMATION OF 3,5-DICYANO-4-(N,N-DIMETHYLFORMAMIDINO)-2,6-DIPHENYL-4H-PYRAN FROM ω-CYANOACETOPHENONE

A 4H-pyran derivative, 3,5-dicyano-4-(N,N-dimethylformamidino)-2,6-diphenyl-4H-pyran (9) was obtained by the reaction of dimethylammonium chloride (5) with ω-cyanoacetophenone (8).