HuagongsheHuagongshe Chemistry Print Report · For research reference only
2H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-
6-nitro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione · 6-Nitroisatoic anhydride · NSC 73615 · 6-Nitro IA · 5-NITROISATOIC ANHYDRIDE · 5-Nitroisatoic anhydride 96% · 6-nitro-1H-3,1-benzoxazine-2,4-dione · 4(1h)-dione,6-nitro-2h-1-benzoxazine-2
Identifiers & Physical Properties
| CAS No. | 4693-02-1 |
|---|---|
| Molecular formula | C8H4N2O5 |
| Average molar mass | 208.13 g/mol |
| Monoisotopic mass | 208.01202123 g/mol |
| SMILES | O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)o1 |
| InChIKey | WWUBAHSWMPFIQZ-UHFFFAOYSA-N |
| PubChem CID | 20821 |
| EC No. | 225-151-1 |
| DTXSID | DTXSID7063558 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 101 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 0 |
| Heavy atoms | 15 |
| Formal charge | 0 |
| Complexity | 323 |
| Melting point | 259 °C |
| Boiling point | 347.31°C (rough estimate) |
| Density | 1.623±0.06 g/cm3 (20 ºC 760 Torr) |
| Refractive index | 1.4900 (estimate) |
| Storage conditions | Sealed in dry,Room Temperature |
| pKa (acidity coefficient) | 9.29±0.20(Predicted) |
| CAS DataBase Reference | 4693-02-1(CAS DataBase Reference) |
| FDA UNII | E3HJ2SF662 |
| EPA Substance Registry System | 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro- (4693-02-1) |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
| TSCA inventory status | TSCA listed |
| Customs code | 2934999090 |
Safety & Regulations
| GHS classification | DangerH301 (92.9%): Toxic if swallowed [Danger Acute toxicity, oral]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264, P264+P265, P270, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (92.9%)Eye Irrit. 2A (100%) |
| TSCA inventory status | TSCA listed |
| Customs code | 2934999090 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| GHS hazard statements | H302-H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
Applications & Uses
Uses
6-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione is a useful research chemical for organic synthesis/bioactive molecule design. 6-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione is also used in the RNA structure probing studies.
Preparation & Synthesis
Preparation
5-Nitroisatoic anhydride is prepared from 5-nitro indole (9g) by stirring in a 4:1 mixture of CH3CN/H2O for 1 h at 40℃. 1 H NMR (DMSO-d6): δ12.34 (s, Br., 1H), 8.59 (s Hz, 1H), 8.51 (d, J = 7.8 Hz, 1H), 7.31 (d, J = 8.7 Hz, 1H).