1,2-Benzenedicarbonitrile, 4-nitro-
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Basic information
- CAS
31643-49-9- Standard SMILES
N#Cc1ccc([N+](=O)[O-])cc1C#N- InChIKey
NTZMSBAAHBICLE-UHFFFAOYSA-N- Molecular formula
- C8H3N3O2
- Average molar mass
- 173.13 g/mol
- Monoisotopic mass
- 173.02252634
Names & identifiers
- Preferred name
- 1,2-Benzenedicarbonitrile, 4-nitro-
- IUPAC
- 4-nitrobenzene-1,2-dicarbonitrile
- English name
- 4-Nitrophthalonitrile
- Molecular formula
- C8H3N3O2
- Molecular weight
- 173.13
Names & synonyms
4-Nitrophthalonitrile31643-49-94-nitrobenzene-1,2-dicarbonitrile5-Nitrobenzene-1,2-dicarbonitrile4-Nitro-1,2-benzenedicarbonitrile3,4-Dicyanonitrobenzene1,2-Benzenedicarbonitrile, 4-nitro-Phthalonitrile, 4-nitro-5-Nitro-1,2-benzenedicarbonitrileNSC 123374EINECS 250-748-9DTXSID4067642
Show more names
4NPN4-NITROPHTALONITRILE4-Nitrophthalodinitrile4-nitro phthalic nitrileROXA-012RSYY（Avanafil)-57TIMTEC-BB SBB0084104-nitro-phthalonitrilp-nitrophthalonitrile
EC 250-748-9RefChem:411090DTXCID1038400250-748-94-Nitro-phthalonitrile1,2-Dicyano-4-nitrobenzeneMFCD000403014-NITROBENZENE-1,2-DINITRILE
Database identifiers
- CAS
31643-49-9- PubChem CID
- 97443
- DTXSID
DTXSID4067642- EC Number
- 250-748-9
- Nikkaji
- J208.808H
Properties
Computed structural propertiesFilling in
- XLogP
- 1.2
- Topological polar surface area
- 93.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 302
Physicochemical properties
- Melting point
- 142 · 142-144 °C(lit.)
- Boiling point
- 303.75 °C · 303.75°C (rough estimate)
- Density
- 1.4553 · 1.4553 (rough estimate)
- refractive index
- 1.65 · 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 · 1877554
- Major Application
- diagnostic assay manufacturinghematologyhistology
- 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 · 31643-49-9(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: No longer Valid Update: 29-06-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/6278
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TI8576000
- 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.
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
Chemistry & industry
Uses & manufacturing
General Manufacturing Information1,2-Benzenedicarbonitrile, 4-nitro-: ACTIVE
Applications
Uses4-Nitrophthalonitrile is a useful chemical in organic synthesis. Dyes and metabolites.
Preparation methods
PreparationSynthesis 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)
Upstream & downstream products
Upstream raw materials
Related reactions
152 records
Compound notes
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