4-Nitrophthalonitrile
- Product Name
- 4-Nitrophthalonitrile
- CAS No.
- 31643-49-9
- Chemical Name
- 4-Nitrophthalonitrile
- Synonyms
- 4-NITROPHTHALONITRILE;4-NITROPHTALONITRILE;4NPN;4-nitro phthalic nitrile;ROXA-012;RSYY（Avanafil)-57;TIMTEC-BB SBB008410;4-nitro-phthalonitril;p-nitrophthalonitrile;Febuxostat Impurity 11
- CBNumber
- CB9102334
- Molecular Formula
- C8H3N3O2
- Formula Weight
- 173.13
- MOL File
- 31643-49-9.mol
4-Nitrophthalonitrile Property
- 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
- 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 DataBase Reference
- 31643-49-9(CAS DataBase Reference)
- EPA Substance Registry System
- 1,2-Benzenedicarbonitrile, 4-nitro- (31643-49-9)
Safety
- 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.
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 330590
- Product name
- 4-Nitrophthalonitrile
- Purity
- 99%
- Packaging
- 5g
- Price
- $316.63
- Updated
- 2025/07/31
- Product number
- N0524
- Product name
- 4-Nitrophthalonitrile
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $68
- Updated
- 2025/07/31
- Product number
- N0524
- Product name
- 4-Nitrophthalonitrile
- Purity
- >98.0%(GC)
- Packaging
- 100g
- Price
- $240
- Updated
- 2025/07/31
- Product number
- N900810
- Product name
- 4-Nitrophthalonitrile
- Packaging
- 2.5g
- Price
- $75
- Updated
- 2021/12/16
- Product number
- 074180
- Product name
- 4-Nitro-1,2-benzenedicarbonitrile
- Purity
- 95+%
- Packaging
- 5g
- Price
- $11
- Updated
- 2021/12/16
4-Nitrophthalonitrile Chemical Properties,Usage,Production
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.
References
[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 Preparation Products And Raw materials
Raw materials
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View Lastest Price from 4-Nitrophthalonitrile manufacturers
- Product
- 5-Nitrobenzene-12-dicarbonitrile 31643-49-9
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-12-17
- Product
- 4-Nitrophthalonitrile 31643-49-9
- Price
- US $76.74/Kg/Drum
- Min. Order
- 25Kg/Drum
- Purity
- 99.50%HPLC
- Supply Ability
- 3tons/month
- Release date
- 2021-09-23
- Product
- 4-Nitrophthalonitrile 31643-49-9
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-20