22856-30-0

Basic information

• Product Name: 2,3-Dicyanonaphthalene
• Synonyms: 2,3-NAPHTHALENEDICARBONITRILE;2,3-DICYANONAPHTHALENE;2 3-NAPHTHALENEDICARBONITRILE 98%;NAPHTHALENE-2,3-DICARBONITRILE ;2,3-DICYANONAHTHALENE;2,3-Naphthalenedicarbonitrile,98%;,3-Dicyanonaphthalene
• CAS NO: 22856-30-0
• Molecular Formula: C₁₂H₆N₂
• Molecular Weight: 178.19
• Product Categories: Functional Materials;Naphthalonitriles (Building Blocks for Naphthalocyanines);Phthalonitriles & Naphthalonitriles;N;Stains and Dyes;Stains&Dyes, A to
• Mol File: 22856-30-0.mol

Chemical Properties

• Melting Point: 253-257 °C
• Boiling Point: 300.41°C (rough estimate)
• Flash Point: 213.4 °C
• Appearance: beige fluffy powder
• Density: 1.2218 (rough estimate)
• Vapor Pressure: 4.46E-07mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: slightly sol. in Chloroform
• BRN: 2574929
• CAS DataBase Reference: 2,3-Dicyanonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dicyanonaphthalene(22856-30-0)
• EPA Substance Registry System: 2,3-Dicyanonaphthalene(22856-30-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-37/39-26
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 22856-30-0(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
2,3-Dicyanonaphthalene is used as a precursor for molecular semiconductors due to its unique chemical structure and properties. It plays a crucial role in the development of advanced electronic devices and materials, contributing to the ongoing advancements in semiconductor technology.
Used in Chemical Industry:
In the chemical industry, 2,3-Dicyanonaphthalene is utilized as a key intermediate in the synthesis of various dyes and metabolites. Its ability to form meta-depside bonds and interact with biopolymers and macromolecules makes it a valuable component in the creation of a diverse array of chemical products.
Used in Pharmaceutical Industry:
2,3-Dicyanonaphthalene also finds application in the pharmaceutical industry, where it serves as a building block for the development of new drugs and therapeutic agents. Its unique chemical properties allow for the creation of novel drug delivery systems, enhancing the bioavailability and therapeutic outcomes of various medications.

InChI:InChI=1/C12H6N2/c13-7-11-5-9-3-1-2-4-10(9)6-12(11)8-14/h1-6H

Upstream product

• 151-50-8 potassium cyanide 
• 125261-31-6 naphthalene-2,3-diyl bis(trifluoromethanesulfonate) 
• 13209-15-9 1,2-bis(dibromomethyl)benzene 
• 764-42-1 1,2-Dicyanoethylene 
• 557-21-1 dicyanozinc 
• 4379-54-8 2,3-Naphthalimide 
• 7664-41-7 ammonia 
• 19005-05-1 2,3-Dicyanobenzobarrelene 
• 92-44-4 2,3-naphthalenediol 
• 764-42-1 butenedinitrile 
• 95-47-6 o-xylene 
• 643-79-8 o-phthalic dicarboxaldehyde 

Downstream Products

• 122681-31-6 titanium(IV) 2,3-naphthalocyanine dichloride 
• 1151520-18-1 3-(4,6-diamino-1,3,5-triazin-2-yl)-2-naphthonitrile 
• 26603-12-3 zinc 2,3-naphthalocyanine 
• 26603-19-0 iron naphthalocyanine 
• 33273-15-3 vanadyl-2,3-naphtalocyanine 
• 86837-58-3 fluoroaluminium 2,3-naphtocyanine 
• 142710-56-3 boron sub-2,3-naphthalocyanine chloride 
• 207389-03-5 [MnCl(C₄H₄C₆H₂C₂N₂)4] 
• 1019776-92-1 C₆₄H₅₇GaN₈O 

Relevant articles and documents

SILICON PHTHALOCYANINE AND A SILICON NAPHTHALOCYANINE: SYNTHESIS, ELECTROCHEMISTRY, AND ELECTROGENERATED CHEMILUMINESCENCE.

The synthesis, spectral characterization, and electrochemical behavior of bis(tri-n-hexylsiloxy)(2,3-phthalocyaninato)silicon left bracket SiPc(OR)//2 right bracket , its dimer left bracket RO(SiPcO)//2R right bracket , and its naphthalocyanine analog left bracket SiNc(OR)//2 right bracket are described. All compounds show near-UV absorption corresponding to Soret and N bands and intense absorption in the visible - near-IR region corresponding to Q bands. In CH//2Cl//2, within the solvent stability limit, there are two reductions and one oxidation for SiPc(OR)//2 and two reductions and two oxidations for RO(SiPcO)//2R and SiNc(OR)//2; all appear as reversible one-electron waves, although n equals 2 for the dimer. The difference in the peak potentials of the first oxidation and first reduction waves agrees well with the excitation energy and fluorescence (corresponding to Q bands) of SiPc(OR)//2 and SiNc(OR)//2.

Photophysical and photochemical properties and aggregation behavior of phthalocyanine and naphthalocyanine derivatives

The photophysical and photochemical properties of phthalocyanine and naphthalocyanine with similar structures were studied in solution and with density-functional theory (DFT) computational method. The extended π-conjugated system in naphthalocyanines causes a bathochromic shift in UV-Vis, emission and excitation bands, and promotes lesser generation of singlet oxygen in solution when compared to phthalocyanines. Time dependent DFT (TD-DFT) calculations point out the molecular orbitals involved in Q-band transition, corresponding to highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) transition with a concentration of charge along x-axis, while the transition to LUMO+1 is in y-axis direction. The presence of tert-butyl substituents does not affect the molecular orbitals shape, but affect their energies. Aggregation studies in dimethyl sulfoxide (DMSO):water solutions showed that naphthalocyanines studied have more aggregation tendency than the phthalocyanines. DFT studies indicated that stacked-dimers are preferred to rotated-stacked conformation due the interaction between ZnII and nitrogen atom from different monomers.

Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction

Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.

The impact of the extended π-conjugation in photophysical, photochemical and aggregation behavior of new phthalocyanine–naphthalocyanine hybrids

We report the synthesis and characterization of phthalocyanine–naphthalocyanine hybrids and the impact of the extended π-conjugation on the macrocycles aggregation, singlet oxygen production, fluorescence lifetime and quantum yields in solution. We observed that the addition of naphthalol units in the structure causes a bathochromic shift in UV-vis, emission and excitation bands and decreases the quantum yield of singlet oxygen in solution.

Iterative synthesis of acenes via homo-elongation

Starting from aromatic ortho-dialdehydes, we devised a homo-elongation protocol that combines a Wittig olefination and subsequent intramolecular Knoevenagel condensation to produce acene diesters and dinitriles. The Royal Society of Chemistry.

An easy route from catechols to phthalonitriles

An easy synthetic route from substituted catechols via their corresponding aryl bistriflates to substituted phthalonitriles is described. The displacement of the triflate groups in catechol triflates by cyanide ions proceeded in high yields using zinc cyanide and palladium-1,1′-bis(diphenylphosphino)ferrocene as catalyst. The mild reaction conditions tolerate numerous functional groups and represent a desirable alternative to the generally low-yielding Rosenmund-von Braun reaction.

SYNTHESIS AND ELECTRICAL PROPERTIES OF A NEW MOLECULAR SEMICONDUCTOR: THE UNSYMMETRICAL LUTETIUM PHTHALONAPHTHALOCYANINE

We propose a new synthetic method for the preparation of PcLuNPc.The electrochemical and electrical properties of thin films of this compound show it is a new molecular semiconductor. - Keywords: phthalocyanines, molecular semiconductors, naphthalocyanines, intrinsic semiconductors, lutetium

Optical recording medium

The present invention relates to an optical recording medium laminated having on a substrate a recording layer comprising an organic thin film containing a silicon naphthalocyanine compound represented by the following general formula (I): wherein L and L' each represents a group capable of linking to silicon.

Electrophotographic plate containing naphthalocyanines which contain siloxy groups

An electrophotographic plate comprising an electroconductive support and a photoconductive layer containing a naphthalocyanine compound having siloxy groups bonded to the central metal silicon as a charge generating substance has high sensitivity to the longer wavelength light of about 800 nm without conducting a special treatment. The naphthalocyanine compound having siloxy groups bonded to the central metal silicon has the following formula: STR1 wherein L is a group of the formula: R1 R2 R3 Si--O--; and R1, R2 and R3 are independently hydrogen, an alkyl group or an alkoxy group.

Metal naphthalocyanine derivative and process for producing the same

A metal naphthalocyanine derivative and process for producing said derivative which is represented by the following formula (I): STR1 wherein M represents germanium or tin; L and L' each independently represent a halogen, a hydroxyl group, an alkyl group, an alkoxy group or a siloxy group of the formula R1 R2 R3 SiO-- (wherein R1, R2 and R3 each independently represent a hydrogen atom, an alkyl group, an alkoxy group or an aryl group).