31643-49-9

Basic information

• Product Name: 5-Nitrobenzene-1,2-dicarbonitrile
• Synonyms: 4-nitro-2-benzenedicarbonitrile;4-nitro-phthalonitril;4-NITRO-1,2-BENZENE DICARBONITRILE;4-NITRO-1,2-DICYANOBENZENE;4-NITRO-O-BENZENEDINITRILE;4-NITROBENZENE-1,2-DINITRILE;4-NITROPHTHALIC ACID DINITRILE;4-NITROPHTHALONITRILE
• CAS NO: 31643-49-9
• Molecular Formula: C₈H₃N₃O₂
• Molecular Weight: 173.13
• EINECS: 250-748-9
• Product Categories: Fluorobenzene;Aromatic Nitriles;Benzene derivates;Nitriles;Functional Materials;Phthalonitriles & Naphthalonitriles;Phthalonitriles (Building Blocks for Phthalocyanines);N;Stains and Dyes;Stains&Dyes, A to;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Aromatic
• Mol File: 31643-49-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 142-144 °C(lit.)
• Boiling Point: 303.75°C (rough estimate)
• Flash Point: 189.6 °C
• Appearance: Light yellow, light greenish or light gray to beige/Crystalline Powder, Crystals and/or Chunks
• Density: 1.4553 (rough estimate)
• Vapor Pressure: 2.76E-06mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
• BRN: 1877554
• CAS DataBase Reference: 5-Nitrobenzene-1,2-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitrobenzene-1,2-dicarbonitrile(31643-49-9)
• EPA Substance Registry System: 5-Nitrobenzene-1,2-dicarbonitrile(31643-49-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TI8576000
• TSCA: Yes
• Hazardous Substances Data: 31643-49-9(Hazardous Substances Data)

Usage

Chemical Properties

light yellow, light greenish or light grey to

Uses

4-Nitrophthalonitrile is a useful chemical in organic synthesis. Dyes and metabolites.

Preparation

Synthesis of 4-Nitrophthalonitrile: SOCl2 (83.5 mL. 1.144 mol) was added dropwise under nitrogen purge to dry DMF (200 mL) which had been cooled to 0-5 °C. The solution was allowed to stir for 15 min at 0-5 °C. The 4-nitrophthalamide (60.1 g, 0.286 mol) was then added and the solution was allowed to slowly warm to room temperature and react for 18 h under nitrogen purge. The solution was then slowly added to ice water to crystallize and precipitate the product. The 4-nitrophthalonitrile was collected using vacuum filtration, washed with ice cold water, and allowed to air dry overnight; yield: 45.2 g (92%); m.p.: 141 °C (det. by DSC) 1 H NMR((CD3)2SO): 8.41 (dd, 1H), 8.67 (dd, 1H), 9.03 (dd, 1H) FTIR: 3091 (m, aromatic C-H stretch), 2242 (d, CN stretch), 1534 (s, asymmetric N=O stretch), 1349 (s, symmetric N=O stretch), 853 (s, C-N stretch)

Synthesis

4-Nitrophthalonitrile synthesized from phthalimide in three steps. The reaction time of ruthenium chloride and HZSM-5 catalysts was very shorter than ammonium molybdate and Hβ catalysts. The yield while we used ruthenium chloride and HZSM-5 catalysts were very higher than another.In a three necked flask, 70 mL of dry dimethylformamide (DMF) was cooled to 0 °C under a stream of nitrogen and 7.3 mL of thionyl chloride was added so that the internal temperature did not go beyond 5 °C. After addition, nitrogen flow was ceased and a calcium chloride tube was added to the top of flask. Meanwhile, the color of the medium was observed to be yellow. Then, 10 g (0.048 mol) of 4- nitrophthalamide was slowly added so that the internal temperature did not go beyond 5 °C. The mixture was stirred over ice bath for 1 hour. The mixture was stirred at room temperature for 2 hours and then poured over 500 g of ice-water. The precipitate was filtered and washed successively with water, 250 mL 5% sodium hydrogencarbonate solution, and water again and dried in a vacuum oven at 110-120 °C. Molecular formula: C8H3N3O2. Yield: 7.4 g (90%). Mp: 141 °C.

InChI:InChI=1/C8H3N3O2/c9-4-6-1-2-8(11(12)13)3-7(6)5-10/h1-3H

Upstream product

• 13138-53-9 4-nitrophthalic amide 
• 91-15-6 phthalonitrile 
• 99-96-7 4-hydroxy-benzoic acid 
• 99-51-4 4-nitro-o-xylene 
• 89-40-7 4-nitrophthalimide 
• 136918-14-4 phthalimide 
• 1033995-63-9 oxonium 
• 24564-72-5 4-nitrophthalic acid chloride 
• 610-27-5 4-nitrophthalic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 130028-42-1 4-([1,3]Dioxolan-4-ylmethoxy)-phthalonitrile 
• 130028-43-2 4-(2,2-Diethyl-[1,3]dioxolan-4-ylmethoxy)-phthalonitrile 
• 83577-72-4 4-[6-(tetrahydro-pyran-2-yloxy)hexyloxy]phthalonitrile 
• 109702-53-6 4-(4-ethylphenoxy) phthalonitrile 
• 73265-04-0 1,12-Bis<3,4-dicyanophenoxy>dodecane 
• 125023-51-0 4-(4–tert-butylphenoxy) phthalonitrile 
• 83482-57-9 4-[4-(1-methyl-1-phenylethyl)phenoxy]-1,2-dicyanobenzene 
• 126993-10-0 N-(3,4-dicyanophenyl)aminoethanol 
• 93673-01-9 1,3-bis(3',4'-dicyanophenoxy)-2,2-dimethylpropane 
• 133863-65-7 4-dodecyl-mercaptophthalonitrile 
• 165406-19-9 1,2-dicyano-4-(2-ethylhexyloxy)benzene 
• 165406-20-2 1,2-dicyano-4-(2,2-dimethyl-3-phenylpropoxy)benzene 
• 86251-74-3 5-nitro-5-(5-nitro-1,3-dioxa-5-cyclohexyl)-1,3-dioxacyclohexane 
• 183059-86-1 4-(p-tolylthio)phthalonitrile 

Relevant articles and documents

A 2-pyridone modified zinc phthalocyanine with three-in-one multiple functions for photodynamic therapy

A 2-pyridone modified zinc phthalocyanine (denoted ZnPc-PYR) achieves a one stone for three birds outcome in the photodynamic therapy (PDT) treatment of cancer. ZnPc-PYR can be excited by both 665 and 808 nm light to treat superficial and deep tumors, store and slowly release singlet oxygen (1O2) to improve its utilization and downregulate the HIF-1 (hypoxia-inducible factor 1) expression level to enhance the tumor cell's sensitivity to PDT treatment under hypoxic conditions.

Palladium(II) phthalocyanines efficiently promote phosphine-free Sonogashira cross-coupling reaction at room temperature

Herein we report that exceptionally simple and inexpensive Pd(II) complexes of phthalocyanines efficiently catalyze direct formation of diphenylacetylenes at ambient conditions with low loading of catalyst (0.5 mol%). Results of this study demonstrate that terminal alkynes reacted mildly with p-substituted aryl bromides at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes in yields up to 98%. Also we have examined this catalyst in Sonogashira cross-coupling with aryl chlorides and it was very effective and this reaction at room temperature that there is no examples in recent articles. This protocol represents the first use of palladium phthalocyanine as homogeneous catalyst in the Pd/Cu-promoted Sonogashira reaction. The palladium(II) phthalocyanine complex is significantly more active in Sonogashira cross-coupling between aryl halides and terminal alkynes as compared with traditional catalysts because of absence of palladium black formation through agglomeration of metal particles and deactivation of catalyst.

New anthracene-based-phtalocyanine semi-conducting materials: Synthesis and optoelectronic properties

A new anthracene-based semi-conducting phtalocyanines AnPc and AnPc-Tr were synthesized in solvent-free conditions. The supramolecular structure of these compounds was confirmed by NMR and FT-IR spectroscopies. Their optical properties were investigated by UV-vis and photoluminescence spectroscopies. The optical gaps were estimated from the absorption-onsets films, and the obtained values were of 1.50 eV and 1.47 eV for AnPc-Tr and AnPc respectively. In solid state, a weaker π-π-interactions of conjugated systems were obtained in the case of AnPc-Tr in comparison with AnPc. This behavior was explained by steric hindrance of triazol groups, which decrease the planarity of macromolecular structure. The HOMO and LUMO levels were estimated using cyclic voltammetry analysis; two phtalocyanine derivatives show a comparable ionization potential. The phtalacyanine containing triazole groups (AnPc-Tr) reveals a higher electron affinity in comparison with AnPc. Single-layer diode devices were fabricated and showed relatively low turn-on voltages.