13001-39-3

Basic information

• Product Name: 1,4-Bis(2-cyanostyryl)benzene
• Synonyms: Benzonitrile,2,2'-(p-phenylenedivinylene)di- (7CI,8CI);2-[(E)-2-[4-[(E)-2-(2-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile
• CAS NO: 13001-39-3
• Molecular Formula: C₂₄H₁₆N₂
• Molecular Weight: 332.4
• EINECS: 235-835-1
• Mol File: 13001-39-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 229-231 °C(Solv: N,N-dimethylformamide (68-12-2))
• Boiling Point: 575.7 °C at 760 mmHg
• Flash Point: 275.3 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated)
• Water Solubility: 24μg/L at 25℃
• CAS DataBase Reference: 1,4-Bis(2-cyanostyryl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis(2-cyanostyryl)benzene(13001-39-3)
• EPA Substance Registry System: 1,4-Bis(2-cyanostyryl)benzene(13001-39-3)

Safety Data

• Hazardous Substances Data: 13001-39-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Synthetic route

2-cyano-benzylphosphonic acid diethyl ester (23973-65-1) + terephthalaldehyde, (623-27-8) → 2-[2-[4-[2-(4-cyanophenyl)vinyl]phenyl]vinyl]benzonitrile (13001-39-3)

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 35℃; for 3h; Solvent; Reagent/catalyst; Green chemistry;	91%
With sodium hydroxide In N,N-dimethyl-formamide at 50℃; for 4h;

2-Methylbenzonitrile (529-19-1) + terephthalaldehyde, (623-27-8) → 2-[2-[4-[2-(4-cyanophenyl)vinyl]phenyl]vinyl]benzonitrile (13001-39-3)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 45℃; for 8h;	12%

2-[2-[4-[2-(4-cyanophenyl)vinyl]phenyl]vinyl]benzonitrile (13001-39-3) → C24H18O4

Conditions	Yield
Stage #1: 2-[2-[4-[2-(4-cyanophenyl)vinyl]phenyl]vinyl]benzonitrile With water; sodium hydroxide In tetrahydrofuran for 36h; Reflux; Stage #2: With formic acid In water	80%

2-[2-[4-[2-(4-cyanophenyl)vinyl]phenyl]vinyl]benzonitrile (13001-39-3) → 2-[2-[4-[2-(2-carboxyphenyl)vinyl]phenyl]vinyl]benzoic acid

Conditions	Yield
With sulfuric acid at 130℃;

Upstream product

• 529-19-1 2-Methylbenzonitrile 
• 623-27-8 terephthalaldehyde, 
• 23973-65-1 2-cyano-benzylphosphonic acid diethyl ester 

Relevant articles and documents

DICYANSTYRYL BENZENE DERIVATIVES AND FLUORESCENT MATERIAL COMPRISING THE SAME

The present invention refers to die [...] benzene derivatives represented by formula 1 are disclosed. The, head of the present invention die [...] benzene to yield fluorescent derivatives (Dicyanstyryl benzene) to minimize environmental pollution by reducing the drain diameter number fluorescent material can be [...] number can be improve. [Formula 1] (by machine translation)

Application of Phase-Transfer Catalysis to the Synthesis of Mono- and Bis-stilbenes and Styryls

A novel and convenient method has been developed for the synthesis of substituted stilbenes by the condensation of active methyl group in suitably substituted toluenes with aromatic aldehydes in aq. medium at room temperature using benzyltriethylammonium chloride as a phase-transfer catalyst.This method has also been applied for the preparation of heterocyclic styryls and extended to the synthesis of bis-stilbenes and bis-styryls using aromatic dialdehydes in place of monoaldehydes.A comparison of the results shows that the present method is superior to the conventional methods in many respects.