5417-82-3

Basic information

• Product Name: (1-ETHOXYETHYLIDENE)MALONONITRILE
• Synonyms: (1-Ethoxyethylidene)-malononitrile, 99+%;2-(1-Ethoxyethylidene)propanedinitrile;(1-Ethoxyethylidene)propane-1,3-dinitrile;(1-Ethoxyethylidene)Malononitrile, 99+% 25GR;(1-Ethoxyethylidene)Malonitrile;2-Cyano-3-ethoxy-3-Methylacrylonitrile;NSC 11585;α-Cyano-β-Methyl-β-ethoxyacrylonitrile
• CAS NO: 5417-82-3
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15
• EINECS: 226-521-5
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;blocks;BuildingBlocks;Carboxes;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 5417-82-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 250.42°C (rough estimate)
• Flash Point: 137.1°C
• Appearance: White to beige/Crystalline Powder and Chunks
• Density: 1.1778 (rough estimate)
• Vapor Pressure: 0.000524mmHg at 25°C
• Refractive Index: 1.5769 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: (1-ETHOXYETHYLIDENE)MALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-ETHOXYETHYLIDENE)MALONONITRILE(5417-82-3)
• EPA Substance Registry System: (1-ETHOXYETHYLIDENE)MALONONITRILE(5417-82-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 3439 6.1/PG 3
• WGK Germany: 3
• RTECS: TY1510000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 5417-82-3(Hazardous Substances Data)

Usage

Chemical Properties

white to beige crystalline powder and chunks

Uses

Different sources of media describe the Uses of 5417-82-3 differently. You can refer to the following data:
1. Herbicide and growth regulator.
2. (1-Ethoxyethylidene)malononitrile was used in the synthesis of benzyl 5-amino-4-cyano-3-methyl-1H pyrazole-1-carboxylate and 2-amino-6-mercaptopyridine-3,5-dicarbonitrile derivatives.

General Description

(1-Ethoxyethylidene)malononitrile is also referred as 2-(1-ethoxyethylidene)malononitrile.

InChI:InChI=1/C7H8N2O/c1-3-10-6(2)7(4-8)5-9/h3H2,1-2H3

Upstream product

• 78-39-7 Triethyl orthoacetate 
• 109-77-3 malononitrile 

Downstream Products

• 34684-87-2 4-amino-2,6-dimethylpyrimidine-5-carbonitrile 
• 54820-92-7 1,3-dimethyl-5-amino-1H-pyrazole-4-carbonitrile 
• 5453-07-6 5-amino-3-methyl-1H-pyrazole-4-carbonitrile 
• 95881-70-2 6-Amino-5-cyano-4-methyl-3-benzenesulfonyl-2-pyridone 
• 76982-30-4 5-amino-1-(3,5-dichlorophenyl)-3-methyl-1H-pyrazole-4-carbonitrile 
• 74455-30-4 3-amino-4-cyan-5-methyl-pyrrol-2-carbonsaeureethylester 
• 76574-44-2 4-amino-6-methyl-pyrimidine-5-carbonitrile 
• 102997-29-5 5-amino-4-cyano-3-methyl-1-ethyl-(1H)-pyrazole 
• 41808-52-0 3-Amino-4-cyano-5-methylisoxazol 
• 1008520-75-9 5-Amino-1-[4-cyano-3-(tetrahydro-pyran-4-ylamino)-phenyl]-3-methyl-1H-pyrazole-4-carbonitrile 
• 1350438-25-3 4-((4-amino-6-cyano-5-methylpyrido[2,3-d]pyrimidin-7-yl)amino)benzenesulfonamide 
• 1350438-27-5 4-((1,7-diaminothieno[3',4':4,5]pyrido[2,3-d]pyrimidin-6-yl)amino)benzenesulfonamide 

Relevant articles and documents

Novel pyrazolo[3,4-d]pyrimidine derivatives inhibit human cancer cell proliferation and induce apoptosis by ROS generation

The paucity of effective anticancer drugs for successful treatment is a major concern, indicating the strong need for novel therapeutic compounds. In the quest of new molecules, the present study aimed to explore the potential of pyrazolo[3,4-d]pyrimidine derivatives as antiproliferative agents. In vitro anticancer screening of selected compounds was done by the National Cancer Institute's Developmental Therapeutics Programme against a panel of 60 cancer cell lines. The lead compound PP-31d considerably inhibited the growth of cancer cells, such as NCI-H460 (non-small-cell lung cancer), OVCAR-4 (ovarian cancer), 786-0 (renal cancer), A549 (non-small-cell lung cancer), and ACHN (renal cancer), showing strong anticancer potential, among other derivatives. Kinetic studies of PP-31d on NCI-H460 cells revealed a dose-dependent effect with an IC50 of 2 μM. The observed inhibition by PP-31d is attributed to the generation of reactive oxygen species and the subsequent induction of cellular apoptosis, as evidenced by the increase in the hypodiploid (subG1) population, the early apoptotic cell population, and caspase-3/7 activity, the loss of the mitochondrial membrane potential, and the degradation of nuclear DNA. Collectively, our results demonstrated that pyrazolo[3,4-d]pyrimidine derivatives inhibit cancer cell proliferation by inducing apoptosis and, thus, have the potential to be further explored for anticancer properties.

An efficient and practical synthesis of 2,4-substituted pyrido[4,3-d]pyrimidin-5(6H)-ones

We describe an efficient synthesis of 2,4-substituted pyrido[4,3-d]pyrimidin-5(6H)-ones, which involves the acid-promoted cyclization of cyano enamine 15 to afford 2,4-bis(methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one 17 as a key intermediate. Selective displacement of the 4-methylthio group by a wide range of anilines followed by oxidation of the 2-methylthio group and subsequent substitution by amines enabled the synthesis of a variety of 2,4-disubstituted pyrido[4,3-d]pyrimidin-5(6H)-ones.

KINASE INHIBITORS AND USES THEREOF

The present disclosure relates generally to compounds and compositions, intermediates, processes for their preparation, and their use as kinase inhibitors.