5-Nitrobenzol-1,2-dicarbonitril

Bezeichnung:5-Nitrobenzol-1,2-dicarbonitril

CAS-Nr31643-49-9

Englisch Name:4-Nitrophthalonitrile

CBNumberCB9102334

SummenformelC8H3N3O2

Molgewicht173.13

MOL-Datei31643-49-9.mol

Synonyma

5-Nitrobenzol-1,2-dicarbonitril

5-Nitrobenzol-1,2-dicarbonitril physikalisch-chemischer Eigenschaften

Schmelzpunkt	142-144 °C(lit.)
Siedepunkt	303.75°C (rough estimate)
Dichte	1.4553 (rough estimate)
Brechungsindex	1.6500 (estimate)
storage temp.	Sealed in dry,Room Temperature
Aggregatzustand	Crystalline Powder, Crystals and/or Chunks
Farbe	Light yellow, light greenish or light gray to beige
Wasserlöslichkeit	Sparingly soluble in water.(0.26 g/L) (25°C),
BRN	1877554
Major Application	diagnostic assay manufacturing hematology histology
InChI	InChI=1S/C8H3N3O2/c9-4-6-1-2-8(11(12)13)3-7(6)5-10/h1-3H
InChIKey	NTZMSBAAHBICLE-UHFFFAOYSA-N
SMILES	C1(C#N)=CC=C([N+]([O-])=O)C=C1C#N
CAS Datenbank	31643-49-9(CAS DataBase Reference)
EPA chemische Informationen	1,2-Benzenedicarbonitrile, 4-nitro- (31643-49-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38-20/21/22
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	TI8576000
TSCA	TSCA listed
HS Code	29269090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxizität	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.

Gefahreninformationscode (GHS)

4-Nitrophthalonitrile Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
light yellow, light greenish or light grey to
Verwenden
4-Nitrophthalonitrile is a useful chemical in organic synthesis. Dyes and metabolites.
synthetische
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)
Synthese
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.
Einzelnachweise
[1] Acta Chemica Scandinavica, 1999, vol. 53, # 9, p. 714 - 720
[2] Materials Research Bulletin, 2016, vol. 75, p. 144 - 154
[3] Heterocycles, 1984, vol. 22, # 9, p. 2047 - 2052
[4] Patent: EP413415, 1991, A1
[5] Russian Chemical Bulletin, 2003, vol. 52, # 1, p. 150 - 153

4-Nitrophthalonitrile Upstream-Materialien And Downstream Produkte

5-Nitrobenzol-1,2-dicarbonitril Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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