14742-32-6

Basic information

• Product Name: 2-AMINO-5-PHENYL-3-FURONITRILE
• Synonyms: AKOS USSH-4110757;2-AMINO-5-PHENYL-FURAN-3-CARBONITRILE;2-AMINO-5-PHENYL-3-FURONITRILE;2-AMINO-3-CYANO-5-PHENYLFURAN;AURORA 20110;BUTTPARK 46\12-26;TIMTEC-BB SBB005514;2-Amino-3-cyano-5-phenylfuran, 2-Amino-5-phenylfuran-3-carbonitrile
• CAS NO: 14742-32-6
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.19
• Mol File: 14742-32-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 196 °C
• Boiling Point: 378.8°Cat760mmHg
• Flash Point: 182.9°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 6.12E-06mmHg at 25°C
• Refractive Index: 1.633
• PKA: -1.66±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-PHENYL-3-FURONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-PHENYL-3-FURONITRILE(14742-32-6)
• EPA Substance Registry System: 2-AMINO-5-PHENYL-3-FURONITRILE(14742-32-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• Hazardous Substances Data: 14742-32-6(Hazardous Substances Data)

Usage

General Description

2-amino-5-phenyl-3-furonitrile is a chemical compound that belongs to the furan-related group of compounds. It is a crystalline solid with a molecular formula C11H8N2O. 2-AMINO-5-PHENYL-3-FURONITRILE is used in organic synthesis and pharmaceutical research as a building block for the synthesis of various biologically active molecules. It has also been studied for its potential pharmacological properties, including its anti-inflammatory and analgesic effects. However, it is important to handle this chemical with care due to its potential health hazards and toxicity.

InChI:InChI=1/C11H8N2O/c12-7-9-6-10(14-11(9)13)8-4-2-1-3-5-8/h1-6H,13H2

Upstream product

• 14476-72-3 2-(2-oxo-2-phenylethyl)malononitrile 
• 70-11-1 α-bromoacetophenone 
• 109-77-3 malononitrile 
• 100805-20-7 5-Amino-2-phenyl-2,3-dihydro-furan-2,4-dicarbonitrile 
• 98-86-2 acetophenone 
• 25939-02-0 4-fluoro-N'-phenylbenzohydrazonoyl chloride 
• 36590-52-0 N-phenyl-p-chlorobenzohydrazonoyl chloride 
• 25939-01-9 p-toluoyl chloride phenylhydrazone 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 5153-67-3 nitrostyrene 

Downstream Products

• 1092938-81-2 methyl 6-{[6-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate 
• 1092938-03-8 Methyl 6-{[5-(5-methylpyridin-2-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanoate 
• 1092938-06-1 methyl 6-{[5-(5-formylpyridin-2-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanoate 
• 1092938-08-3 Methyl 6-{[6-phenyl-5-(5-vinylpyridin-2-yl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate 
• 1092938-10-7 Methyl 6-{[5-(5-ethylpyridin-2-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanoate 
• 1092938-13-0 tert-Butyl (6R)-6-{[5-(5-ethylpyridin-2-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}heptanoate 
• 1092938-16-3 tert-butyl (6R)-6-[(5-cyclopent-1-en-1-yl-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]heptanoate 
• 1092938-55-0 (6R)-6-{[5-(4-ethylcyclohex-1-en-1-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid 
• 1092938-27-6 tert-butyl (6R)-6-{[5-(4-ethylcyclohex-1-en-1-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}heptanoate 
• 1093066-22-8 (6R)-6-{[5-(4-Ethylcyclohexyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid 
• 1093386-36-7 ethyl (-)-2-{(2R)-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]-2-methylpropyloxy}acetate 
• 1092938-73-2 methyl (3-{[5-(5-ethylpyridin-2-yl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxy)acetate 
• 220696-22-0 5-phenyl-2-(1-pyrrolyl)-3-furonitrile 

Relevant articles and documents

Design and synthesis of novel furan, furo[2,3-d]pyrimidine and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as potential VEGFR-2 inhibitors

Novel furan 6a-c, furo[2,3-d]pyrimidine 7a-f, 9, 10a-f, 12a,b, 14a-d and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine 8a-f derivatives were designed based on their structural similarity to a previously described oxazole VEGFR-2 back pocket binding fragment. The designed compounds were synthesized and screened for their in vitro VEGFR-2 inhibitory activity where they exhibited good to moderate nanomolar inhibition with improved ligand efficiencies. 8b and 10c (IC50 = 38.72 ± 1.7 and 41.40 ± 1.8 nM, respectively) were equipotent to sorafenib and 6a, 6c, 7f, 8a, 8c, 10b, 10f, 12b, 14c and 14d showed good activity (IC50 = 43.31–98.31 nM). The furotriazolopyrimidines 8a-c and furopyrimidine derivative 10c were further evaluated for their in vitro antiproliferative activity against human umbilical vein endothelial cells (HUVECs) where 8b showed higher potency than sorafenib and resulted in cell cycle arrest at G2/M phase whereas 8c revealed good antiproliferative activity with cell cycle arrest at G1 phase. Moreover, 8a-c and 10c showed significant inhibitory effects on the invasion and migration of HUVECs. Molecular docking study was conducted to gain insight about the potential binding mode. The furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives 8b and 8c represent interesting starting point for antiangiogenic compounds based on their activity and favorable drug likeness profiles.

One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity

Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.

Novel, Cyclically Substituted Furopyrimidine Derivatives and Use Thereof

The present application relates to novel, cyclically substituted furopyrimidine derivatives, methods for their production, their use for the treatment and/or prophylaxis of diseases and their use for the production of medicinal products for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.