2286-56-8

Basic information

• Product Name: ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE
• Synonyms: alpha-cyano-3,4-methylenedioxycinnamicacidethylester;alpha-cyano-3,4-methylenedioxy-cinnamicaciethylester;ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE;RARECHEM AK ML 0021;BRN 0089472;2-Cyano-3-(1,3-benzodioxol-5-yl)propenoic acid ethyl ester;3-(1,3-Benzodioxole-5-yl)-2-cyanoacrylic acid ethyl ester;α-Cyano-1,3-benzodioxole-5-acrylic acid ethyl ester
• CAS NO: 2286-56-8
• Molecular Formula: C₁₃H₁₁NO₄
• Molecular Weight: 245.23
• Mol File: 2286-56-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 95-97°C
• Boiling Point: 397.1°Cat760mmHg
• Flash Point: 173.7°C
• Appearance: /
• Density: 1.305g/cm³
• Vapor Pressure: 1.63E-06mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE(2286-56-8)
• EPA Substance Registry System: ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE(2286-56-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2286-56-8(Hazardous Substances Data)

Usage

General Description

ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE, also known as Ethyl 3-(2-cyanoacryloyl)-1,3-benzodioxole-5-carboxylate, is a chemical compound with the molecular formula C13H9NO5. It is an ester derivative of cyanoacrylic acid and is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. ETHYL 3-(1,3-BENZODIOXOL-5-YL)-2-CYANOACRYLATE has been studied for its potential use in the development of novel drugs and it may exhibit biological activity due to its structural features. However, it is important to handle this chemical with caution as it may pose health and safety risks if not used properly.

InChI:InChI=1/C13H11NO4/c1-2-16-13(15)10(7-14)5-9-3-4-11-12(6-9)18-8-17-11/h3-6H,2,8H2,1H3/b10-5+

Upstream product

• 120-57-0 piperonal 
• 64-17-5 ethanol 
• 105-56-6 ethyl 2-cyanoacetate 
• 14683-73-9 N,N'-benzo[1,3]dioxol-5-ylmethanediyl-bis-acetamide 
• 4543-59-3 1,2-bis(3,4-dioxymethylenephenyl)ethane-1,2-diol 
• 51066-70-7 2-cyano-3-(3',4'-methylenedioxy-1'-phenyl)acrylic acid 

Downstream Products

• 133405-30-8 2-Amino-4-benzo[1,3]dioxol-5-yl-6-thiophen-2-yl-isophthalonitrile 
• 133379-54-1 3-Amino-5-benzo[1,3]dioxol-5-yl-biphenyl-2,4-dicarbonitrile 
• 313967-78-1 ethyl 2-amino-4-(benzo[d][1,3]dioxol-5-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate 
• 313967-78-1 ethyl 2-amino-4-(benzo[d][1,3]dioxol-5-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate 
• 1372801-03-0 (1R,2R,6R)-triethyl 6-(benzo[d][1,3]dioxol-5-yl)-1-cyanocyclohex-3-ene-1,2,3-tricarboxylate 
• 1385784-13-3 ethyl-2-amino-5-cyano-1-[1-(2,5-dimethoxyphenyl)ethylideneamino]-6-oxo-4-(benzo[d][1,3]dioxol-5-yl)-1,6-dihydropyridine-3-carboxylate 
• 1334176-96-3 (Z)-7-(benzo[d][1,3]dioxol-5-ylmethylene)-3-phenyl-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]triazin-6(7H)-one 

Relevant articles and documents

A novel Golgi mannosidase inhibitor: Molecular design, synthesis, enzyme inhibition, and inhibition of spheroid formation

Effective chemotherapy for solid cancers is challenging due to a limitation in permeation that prevents anticancer drugs from reaching the center of the tumor, therefore unable to limit cancer cell growth. To circumvent this issue, we planned to apply the drugs directly at the center by first collapsing the outer structure. For this, we focused on cell–cell communication (CCC) between N-glycans and proteins at the tumor cell surface. Mature N-glycans establish CCC; however, CCC is hindered when numerous immature N-glycans are present at the cell surface. Inhibition of Golgi mannosidases (GMs) results in the transport of immature N-glycans to the cell surface. This can be employed to disrupt CCC. Here, we describe the molecular design and synthesis of an improved GM inhibitor with a non-sugar mimic scaffold that was screened from a compound library. The synthesized compounds were tested for enzyme inhibition ability and inhibition of spheroid formation using cell-based methods. Most of the compounds designed and synthesized exhibited GM inhibition at the cellular level. Of those, AR524 had higher inhibitory activity than a known GM inhibitor, kifunensine. Moreover, AR524 inhibited spheroid formation of human malignant cells at low concentration (10 μM), based on the disruption of CCC by GM inhibition.

Knoevenagel condensation of aldehydes with active methylene compounds catalyzed by MgC2O4/SiO2 under microwave irradiation and solvent-free conditions

MgC2O4/SiO2 catalyzes the efficient Knoevenagel condensation of aldehydes with active methylene compounds in solvent-free conditions under microwave irradiation to give alkenes derivatives in excellent yields. MgC2/s

Efficient asymmetric synthesis of 4H-chromene derivatives through a tandem michael addition-cyclization reaction catalyzed by a salen-cobalt(II) complex

The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates. Moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee) were obtained with a chiral salen-cobalt(II) complex. This process was air tolerant and easily performed, which provides an efficient method for the synthesis of chiral 4H-chromene derivatives. The asymmetric synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione and ethyl 2-cyano-3-phenylacrylates catalyzed by a chiral salen-cobalt(II) complex with moderate to good yields (up to 81%) and high enantioselectivities (up to 89%ee).