3029-30-9

Basic information

• Product Name: 1,4-DICYANONAPHTHALENE
• Synonyms: 1,4-NAPHTHALENEDICARBONITRILE;1,4-DICYANONAPHTHALENE;NAPHTHALENE-1,4-DICARBONITRILE;NAPHTHALENE-1,4-DICARBONITRILE, 98+%;Naphthalin-1,4-dicarbonitril;1,4-Dcyanonaphthalene;1,4-Nphthalenedicarbonitrile
• CAS NO: 3029-30-9
• Molecular Formula: C₁₂H₆N₂
• Molecular Weight: 178.19
• EINECS: 221-197-1
• Mol File: 3029-30-9.mol

Chemical Properties

• Melting Point: 209-211°C
• Boiling Point: 401.2 °C at 760 mmHg
• Flash Point: 205 °C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 1.21E-06mmHg at 25°C
• Refractive Index: 1.663
• BRN: 1870226
• CAS DataBase Reference: 1,4-DICYANONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DICYANONAPHTHALENE(3029-30-9)
• EPA Substance Registry System: 1,4-DICYANONAPHTHALENE(3029-30-9)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 22-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3029-30-9(Hazardous Substances Data)

Usage

Uses

1. Used in Biological Studies:
1,4-Dicyanonaphthalene is used as a component in the electron transfer mechanism of nucleic acid precursors and circular thermal DNA (ctDNA) with protein enzymes. It plays a crucial role in facilitating the transfer of electrons between these biological molecules, which is essential for various cellular processes.
2. Used in Fluorescence Probes:
1,4-Dicyanonaphthalene is utilized in the development of several fluorescence probes that can be used to study both static and excited states of molecules. Its unique electronic properties make it an ideal candidate for designing probes that can detect and monitor molecular interactions, conformational changes, and other biological events with high sensitivity and specificity.

Purification Methods

Purify it by recrystallization from EtOH (charcoal), m 208o, and sublime it in vacuo. [Bradbrook & Linstead J Chem Soc 1742 1936, Beilstein 9 H 917, 9 II 651, 9 III 464.]

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

Upstream product

• 58692-14-1 syn-1,2:3,4-naphthalene dioxide 
• 151-50-8 potassium cyanide 
• 83-53-4 1,4-dibromonaphthalene 
• 544-92-3 copper(I) cyanide 
• 129278-41-7 C₁₆H₁₁BrN₂S 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 100-39-0 benzyl bromide 
• 2746-25-0 p-Methoxybenzyl bromide 
• 76509-15-4 2,3-Bis(2,4-dimethylphenylamino)-1,2,3,4-tetrahydronaphthalin-1,4-dicarbonitril 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 104-81-4 4-Methylbenzyl bromide 
• 28227-42-1 1,4-di-tert-butyl-1,4-diazabutadiene 
• 613-73-0 1,2-phenylenediacetonitrile 
• 28227-41-0 1,4-diisopropyl-1,4-diazabuta-1,3-diene 

Downstream Products

• 605-70-9 naphthalene-1,4-dicarboxylic acid 
• 145866-37-1 [4-(1,4-Dicyano-1,2-dihydro-naphthalen-1-ylmethyl)-phenyl]-acetic acid methyl ester 
• 83242-05-1 1-Benzyl-1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 83242-06-2 2-benzyl-1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 154463-61-3 1-(Hydroxymethyl)-1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 79996-90-0 4-(Hydroxymethyl)-1-naphthalenecarbonitrile 
• 78075-59-9 4-benzyl-1-naphthalenecarbonitrile 
• 98689-34-0 3-Benzylnaphthalene-1-carbonitrile 
• 86-53-3 1-Cyanonaphthalene 
• 3962-43-4 1,2-diphenyl-1,2-dimethoxy ethane, meso 
• 83242-12-0 1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 109873-05-4 1-(Methoxy-phenyl-methyl)-1,2-dihydro-naphthalene-1,4-dicarbonitrile 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Kinetics of C-C and C-H bond cleavage in phenyl alkane radical cations generated by photoinduced electron transfer

Employing nanosecond laser flash photolysis, we determined the relative importance of two fragmentation modes, namely, C-C bond cleavage and deprotonation, for the radical cation of 1,1,2,2-tetraphenylethane photogenerated by electron transfer to cyanoaromatic singlet excited states in acetonitrile at room temperature. Analysis of the kinetic data for this phenyl alkane suggests that the C-C bond cleavage dominates over the deprotonation by a ratio of about 2:1. In addition, the deprotonation kinetics of diphenylmethane, 1,1-diphenylethane, triphenylmethane, and several phenyl-substituted alcohols have been investigated. To aid identification and characterization, experiments based on two laser pulses in tandem (308 and 337.1 nm) were performed to probe fluorescence and photochemistry of the transient radicals formed as products of radical ion fragmentation. The first-order rate constants for growth of transient absorptions due to fragmentation-derived radicals were measured to be ≥1 × 106 s-1. Activation parameters, with activation enthalpies in the range 10-18 kJ/mol and activation entropies between -60 and -91 J/(mol.K), are also reported for fragmentation kinetics of radical cations of several systems under study. (Graph Presented).

Triphenylbismuth Dichloride-Mediated Conversion of Thioamides to Nitriles

Thioamides were efficiently converted to nitriles using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process was also successfully extended to the synthesis of cyanamides starting from the corresponding thioureas and of thiocyanates from dithiocarbamates.

Catalytic Dehydrosulfurization of Thioamides to Nitriles by Gold Nanoparticles Supported on Carbon Nanotubes

A gold-carbon nanotube nanohybrid was shown to act as an efficient heterogeneous catalyst in the smooth and selective conversion of thioamides to the corresponding nitriles. The reaction was performed under mild conditions (room temperature, atmospheric pressure of oxygen) using only a gold loading of 0.35 mol %. Substituted aromatic or aliphatic nitriles were produced in very good to excellent yields and the catalyst could be easily recycled and reused over several consecutive cycles with no loss in dehydrosulfurization performances.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

Corresponding amine nitrile and method of manufacturing thereof

The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.

Environmentally benign and economic synthesis of covalent triazine-based frameworks

Covalent triazine-based frameworks (CTFs) are important microporous materials with a wide range of applications. Here, we demonstrate an environmentally benign and economic synthetic pathway to CTFs. The monomers used for CTFs, aromatic nitriles, were obtained by cyanation using nontoxic potassium hexacyanoferrate(II) in place of commonly used toxic cyanides. Then, the CTFs were synthesized by trimerization of the corresponding cyano monomers in molten zinc chloride. A series of CTFs was synthesized, and the highest Brunauer-Emmett-Teller surface area measured in this series was 2404 m2/g. Among the synthesized CTFs, CTFDCP exhibited excellent CO2 adsorption properties, with a CO2 uptake of 225 mg/g at 0 °C.

Corresponding amine nitrile and method of manufacturing thereof (by machine translation)

The invention relates to a method of manufacturing one kind of nitrile, compared with the prior art, has significantly reduced the amount of ammonia, the environmental pressure of the small, low energy consumption, low production cost, nitrile product purity and yield and the like, and can obtain more complex structure of the nitriles. The invention also relates to the corresponding amine by the nitrile manufacture method. (by machine translation)

An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid

Aryl and arylvinyl nitriles have been prepared in good yields from the corresponding bromides with potassium hexacyanoferrate (II) using palladium-catalyzed reactions in ionic liquid under microwave irradiation. Georg Thieme Verlag Stuttgart.

Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene

High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic biomination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.