4-Nitrophthalonitrile Chemical Properties

Melting point:

142-144 °C(lit.)

Boiling point:

303.75°C (rough estimate)

Density 

1.4553 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder, Crystals and/or Chunks

color 

Light yellow, light greenish or light gray to beige

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

BRN 

1877554

CAS DataBase Reference

31643-49-9(CAS DataBase Reference)

EPA Substance Registry System

1,2-Benzenedicarbonitrile, 4-nitro- (31643-49-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

TI8576000

TSCA 

Yes

HS Code 

29269090

Toxicity

mouse,LD50,oral,500mg/kg (500mg/kg),SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTIONBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION,Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(9), Pg. 92, 1987.

MSDS

• Language:English Provider:5-Nitrobenzene-1,2-dicarbonitrile
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-Nitrophthalonitrile Usage And Synthesis

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.

4-Nitrophthalonitrile(31643-49-9)Related Product Information

• 4-Nitrophthalic acid
• 4-(2-Methylpropoxy)-1,3-benzenedicarbothioaMide
• Febuxostat Impurity 8
• isopropyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE
• ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• 3-Cyano-4-isobutoxybenzoic acid
• FeBuxostat Impurity 33
• Febuxostat impurity 37
• Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
• Febuxostat-d9
• 2-[3-(AMinocarbonyl)-4-(2-Methylpropoxy)phenyl]-4-Methyl-5-thiazolecarboxylic Acid
• 2-[3-Carboxy-4-(2-Methylpropoxy)phenyl]-4-Methyl-5-thiazolecarboxylic Acid
• 2-HYDROXY-THIOBENZAMIDE
• 3-Cyano-4-(2-methylpropoxy)benzenecarbothioamide
• Febuxostat Impurity 6
• 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid
• 4-ISOBUTOXY-BENZALDEHYDE