3785-90-8

Basic information

• Product Name: 4-HYDROXYBENZYLIDENEMALONONITRILE
• Synonyms: RARECHEM AL BX 0098;P-HYDROXYBENZYLIDINEMALONONITRILE;TYRPHOSTIN A8;TYRPHOSTIN AG 10;4-HYDROXYBENZYLIDENEMALONODINITRILE;4-HYDROXYBENZYLIDENEMALONONITRILE;(4-HYDROXYBENZYLIDENE)MALEONITRILE;AG 10
• CAS NO: 3785-90-8
• Molecular Formula: C₁₀H₆N₂O
• Molecular Weight: 170.17
• EINECS: 223-253-0
• Mol File: 3785-90-8.mol
• Article Data: 110

Chemical Properties

• Melting Point: 186-189 °C
• Boiling Point: 301.15°C (rough estimate)
• Flash Point: 168.1 °C
• Appearance: Yellow solid
• Density: 1.2047 (rough estimate)
• Vapor Pressure: 1.66E-05mmHg at 25°C
• Refractive Index: 1.7040 (estimate)
• Storage Temp.: 2-8°C
• Solubility: ethanol: 20 mg/mL, clear
• PKA: 7.37±0.13(Predicted)
• BRN: 2209079
• CAS DataBase Reference: 4-HYDROXYBENZYLIDENEMALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYBENZYLIDENEMALONONITRILE(3785-90-8)
• EPA Substance Registry System: 4-HYDROXYBENZYLIDENEMALONONITRILE(3785-90-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: OO4200000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3785-90-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow amorphous powder

Uses

Inhibitor of transducin GTPase activity

InChI:InChI=1/C10H6N2O/c11-6-9(7-12)5-8-1-3-10(13)4-2-8/h1-5,13H

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 109-77-3 malononitrile 
• 90-15-3 α-naphthol 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 59276-27-6 4-(dimethoxymethyl)phenol 
• 114569-19-6 N-(p-hydroxybenzylidene)-p-aminoacetophenone 
• 100-67-4 potassium phenolate 
• 62309-99-3 phenoxymethylene-malononitrile 

Downstream Products

• 19310-87-3 4-(2,2-dicyanovinyl)phenyl acetate 
• 132524-80-2 2-amino-5,6-dihydro-4-(4-hydroxyphenyl)-6-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carbonitrile 
• 130944-11-5 2-amino-4-(4-hydroxyphenyl)-4H-benzo[h]chromene-3-carbonitrile 
• 130944-13-7 2-amino-4-(4-hydroxyphenyl)-4H-benzo[f]chromene-3-carbonitrile 
• 272785-41-8 4-(2,2-dicyanovinyl)-2-phenyliodoniophenolate 

Relevant articles and documents

Photoacid as ICT probe for ground state proton transfer process from solute to solvents

In present work, 2-(4-Hydroxybenzylidene)malononitrile (HyDC) acts as a photoacid and intramolecular charge transfer (ICT) probe for monitoring solvent specific ground state proton transfer (GSPT) process from solute to solvents. Presence of electron accepting group in HyDC, photoacidic nature and GSPT process are enhanced and observed by UV–Vis spectroscopy. HyDC shows microsolvation behavior with protic solvents at ground state. Microsolvated clusters of HyDC with solvents are formed and supported by experimental and theoretical results.

Supported copper on a diamide-diacid-bridged PMO: an efficient hybrid catalyst for the cascade oxidation of benzyl alcohols/Knoevenagel condensation

In this study, a novel periodic mesoporous organosilica (PMO) containing diamide-diacid bridges was conveniently prepared using ethylenediaminetetraacetic dianhydride to support Cu(ii) species and affording supramolecular Cu@EDTAD-PMO nanoparticles efficiently. Fourier transform infrared (FT-IR) and energy dispersive X-ray (EDX) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), Brunauer-Emmett-Teller (BET) analysis, and high-resolution transmission electron microscopy (HRTEM) results confirmed the successful synthesis of Cu@EDTAD-PMO. The stabilized Cu(ii) nanoparticles inside the mesochannels of the new PMO provided appropriate sites for selective oxidation of different benzyl alcohol derivatives to their corresponding benzaldehydes and subsequent Knoevenagel condensation with malononitrile. Therefore, Cu@EDTAD-PMO can be considered as a multifunctional heterogeneous catalyst, which is prepared easily through a green procedure and demonstrates appropriate stability with almost no leaching of the Cu(ii) nanoparticles into the reaction medium, and easy recovery through simple filtration. The recycled Cu@EDTAD-PMO was reused up to five times without significant loss of its catalytic activity. The stability, recoverability, and reusability of the designed heterogeneous catalyst were also studied under various reaction conditions.

Introduction of succinimide as a green and sustainable organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b] pyran derivatives

Aim and Objective: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives

Design and Development of Amine Functionalized Mesoporous Cubic Silica Particles: A Recyclable Catalyst for Knoevenagel Condensation

Abstract: The amine functionalized cubic mesoporous silica nanoparticles (cSiO2-NH2) were successfully synthesized through biphasic stratification approach. The synthesized material was characterised by various spectroscopic and phys