| Identification | More | [Name]
5-Nitrobenzene-1,2-dicarbonitrile | [CAS]
31643-49-9 | [Synonyms]
1,2-DICYANO-4-NITROBENZENE
3,4-DICYANO-1-NITROBENZENE
3,4-DICYANONITROBENZENE
4-NITRO-1,2-BENZENE DICARBONITRILE
4-NITRO-1,2-DICYANOBENZENE
4-NITROBENZENE-1,2-DINITRILE
4-NITRO-O-BENZENEDINITRILE
4-NITROPHTHALIC ACID DINITRILE
4-NITROPHTHALONITRILE
5-Nitrobenzene-1,2-dicarbonitrile
PHTHALONITRILE, 4-NITRO-
TIMTEC-BB SBB008410
4-nitro-2-benzenedicarbonitrile
4-nitro-phthalonitril
4-Nitrophthalonitrile99%
4-nitro-1,2-benzendicarbonitrile
4-Nitro-1,2-benzene-dicarbonitrile（4-nitrophthalonitrile）
4-nitro-2-benzenedicarbonitril
1,2-Benzenedicarbonitrile, 4-nitro-
4-NITROPHTALONITRILE | [EINECS(EC#)]
250-748-9 | [Molecular Formula]
C8H3N3O2 | [MDL Number]
MFCD00040301 | [Molecular Weight]
173.13 | [MOL File]
31643-49-9.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow, light greenish or light grey to | [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]
31643-49-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [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. |
| Hazard Information | Back Directory | [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]
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.
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