118132-11-9

Basic information

• Product Name: 4,5-DIOCTYLOXY-1,2-BENZENEDICARBONITRILE
• Synonyms: 4,5-DIOCTYLOXY-1,2-BENZENEDICARBONITRILE;4,5-DIOCTYLOXYPHTHALONITRILE;4,5-DIOCTYLOXY-1,2-BENZENEDICARBONITRILE 97%;4,5-bis(octyloxy)-1,2-benzenedicarbonitrile;4,5-dioctoxybenzene-1,2-dicarbonitrile
• CAS NO: 118132-11-9
• Molecular Formula: C₂₄H₃₆N₂O₂
• Molecular Weight: 384.55
• Product Categories: Building Blocks;C10 to C27;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 118132-11-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 106-108 °C(lit.)
• Boiling Point: 529.3°C at 760 mmHg
• Flash Point: 181.6°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 2.75E-11mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 4,5-DIOCTYLOXY-1,2-BENZENEDICARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIOCTYLOXY-1,2-BENZENEDICARBONITRILE(118132-11-9)
• EPA Substance Registry System: 4,5-DIOCTYLOXY-1,2-BENZENEDICARBONITRILE(118132-11-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 118132-11-9(Hazardous Substances Data)

Usage

Description

4,5-Dioctyloxy-1,2-benzenedicarbonitrile, also known as 4,5-Dioctyloxyphthalonitrile, is an organic compound with the molecular formula C20H27N3O2. It is characterized by its octyloxy substituents and dicyano groups, which contribute to its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
4,5-Dioctyloxy-1,2-benzenedicarbonitrile is used as a key intermediate for the preparation of new unsymmetrically substituted DB24C8-phthalocyanines. These phthalocyanines have potential applications in the development of novel pharmaceutical compounds, particularly in the area of cancer treatment and imaging.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4,5-Dioctyloxy-1,2-benzenedicarbonitrile is utilized for the synthesis of tetrathiafluvalene (TTF)-annulated symmetrical and unsymmetrical phthalocyanines. These compounds are of interest due to their unique electronic properties and potential applications in various areas, such as organic electronics, sensors, and catalysis.
Used in Material Science:
The unique structure and properties of 4,5-Dioctyloxy-1,2-benzenedicarbonitrile make it a promising candidate for the development of new materials with specific characteristics. For example, it can be used in the synthesis of novel phthalocyanine-based materials with tailored properties for applications in areas such as solar energy conversion, light-emitting diodes (LEDs), and nonlinear optics.

InChI:InChI=1/C24H36N2O2/c1-3-5-7-9-11-13-15-27-23-17-21(19-25)22(20-26)18-24(23)28-16-14-12-10-8-6-4-2/h17-18H,3-16H2,1-2H3

Upstream product

• 111-87-5 octanol 
• 4956-41-6 1,2-dioctyloxybenzene 
• 111-83-1 1-bromo-octane 
• 300853-66-1 4,5-dihydroxyphthalonitrile 
• 2563-26-0 4,5-dibromobenzene-1,2-diol 
• 120-80-9 benzene-1,2-diol 
• 118132-04-0 1,2-Dibromo-4,5-bis(octyloxy)benzene 
• 544-92-3 copper(I) cyanide 
• 118156-18-6 1,3-dihydro-1,3-diimino-5,6-bis(octyloxy)isoindole 

Downstream Products

• 118156-18-6 1,3-dihydro-1,3-diimino-5,6-bis(octyloxy)isoindole 
• 261504-18-1 2,3,9,10,16,17,23,24-octakis(octyloxy)-29H,31H-phthalocyanine 
• 1639428-88-8 C₁₄₄H₁₈₆N₁₂O₁₄Zn 
• 1639428-89-9 C₁₃₄H₁₈₀N₁₀O₁₃Zn 
• 1639428-90-2 C₅₂H₆₆N₂O₆ 
• 119495-09-9 2,3,9,10,16,17,23,24-octakis(octyloxy)phthalocyanine-copper(II) 

Relevant articles and documents

Liquid crystalline octasubstituted lead(ii) phthalocyanines: Effects of alkoxy and alkylthio substituents on film alignment and electrical properties

Octasubstituted lead(ii) phthalocyanines containing alkylthio- and alkoxy- groups in peripheral positions have been synthesized and characterized using 1H and 13C NMR, UV-Vis, IR and mass spectroscopies as well as elemental analysis. The mesogenic properties of the octasubstituted lead(ii) phthalocyanines have been investigated by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction. The sandwich structures ITO/PbPc/In were prepared to investigate the J(V) characteristics of thin films of these molecules. The dissimilar behavior of the films before and after heat-treatment is expected to result in changing the alignment inside the columnar stacking of the molecules in the films.

SYNTHESIS AND CHARACTERIZATION OF SOLUBLE PHTHALOCYANINES: STRUCTURE-PROPERTY RELATIONSHIP

(μ-Oxo)bis 6a-c are obtained by treatment of the cyclotetramerisation product of 4,5-bis(alkoxy)-phthalonitriles in lithium pentanolate with iron(II) acetate.Compounds 6a-c are reduced to bisaxially coordinated octaalkoxyphthalocyaninatoiron(II) in the presence of ligands such as pyridine and t-butylisocyanide. reaction of 6a with bidentate bridging ligands (e.g. pyrazine, 1,4-dicyanobenzene) yields the bridged complexes 8a and 9a.The Moessbauer spectroscopic data are described and compared with the analogous unsubstituted phthalocyaninatoiron derivatives.

Evidence of an ordered columnar mesophase in peripherally octa-n-alkoxy-substituted phthalocyanines

Liquid crystalline phthalocyanines with eight n-alkoxy chains have been synthesized and their mesophase structures determined by X-ray diffraction.The mesophases appear to be of the Dho type.Reasons for the preference of ordered columns are dis