6-Chloro-3-nitropyridin-2-ylamine
6-CHLORO-3-NITROPYRIDIN-2-AMINE · LABOTEST-BB LT00012599 · 2-Amino-6-chloro-3-nitrop... · 2-amino-3-nitrochloropyridine · 6-Chlor-3-nitropyridin-2-amin · 2-Amino-3-nitro-6-chloropyridi · 2-Amino-6-chloro-nitro pyridne · 2-Amino-6-chlor-3-nitropyridin
Identifiers & Physical Properties
| CAS No. | 27048-04-0 |
|---|---|
| Molecular formula | C5H4ClN3O2 |
| Average molar mass | 173.56 g/mol |
| Monoisotopic mass | 172.99920405 g/mol |
| SMILES | Nc1nc(Cl)ccc1[N+](=O)[O-] |
| InChIKey | WERABQRUGJIMKQ-UHFFFAOYSA-N |
| PubChem CID | 2724035 |
| EC No. | 248-188-5 |
| DTXSID | DTXSID40181524 |
Chemical & Physical Properties
| XLogP | 1.8 |
|---|---|
| Topological polar surface area | 84.7 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 0 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 160 |
| Melting point | 195-196 |
| Boiling point | 339.9±37.0 °C(Predicted) |
| Density | 1.596±0.06 g/cm3(Predicted) |
| Storage conditions | Keep in dark place,Inert atmosphere,2-8°C |
| Solubility | Chloroform, DMSOSlightly soluble in water. Soluble in dimethyl sulfoxide and chloroform. |
| Physical state | Crystalline |
| pKa (acidity coefficient) | -1.69±0.50(Predicted) |
| Color | Yellow |
| InChI | InChI=1S/C5H4ClN3O2/c6-4-2-1-3(9(10)11)5(7)8-4/h1-2H,(H2,7,8) |
| InChIKey | WERABQRUGJIMKQ-UHFFFAOYSA-N |
| SMILES | C1(N)=NC(Cl)=CC=C1[N+]([O-])=O |
| CAS DataBase Reference | 27048-04-0(CAS DataBase Reference) |
| GHS pictogram | GHS06 |
| Signal word | Warning |
| GHS hazard statements | H302-H312-H315-H319-H331-H335 |
| GHS precautionary statements | P261-P280-P304+P340-P305+P351+P338-P405-P501a |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 22-26-36/37/39 |
| UN transport number | 2811 |
| Hazard Note | Irritant |
| Hazard class | 6.1 |
| Packing group | Ⅲ |
| Customs code | 29333999 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 5.3% (1 of 19) of reports.WarningH302 (21.1%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, 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 19 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Status: Active Update: 15-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23183 |
| Hazard Classes and Categories | Acute Tox. 4 (21.1%) |
| UN transport number | 2811 |
| Customs code | 29333999 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS06 |
| Hazard symbols | Xi |
| hazard_note | Irritant |
| Safety statements (S) | 22-26-36/37/39 |
| Hazard class | 6.1 |
| Packing group | Ⅲ |
| GHS hazard statements | H302-H312-H315-H319-H331-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P280-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
Description
2-Amino-6-chloro-3-nitropyridine is a cytotoxic drug that has been shown to have anti-viral potency, as well as antiviral activity in an activity test. It is synthesized by reacting hydrogen tartrate with oxadiazole, and then hydrolyzing the resulting product with chloride. 2-Amino-6-chloro-3-nitropyridine has also been shown to inhibit human immunodeficiency virus type 1 (HIV) replication in vitro and to be effective against other viruses such as type 2 influenza. This drug can bind to the viral envelope and inhibit fusion of the viral membrane with host cells by preventing the release of viral contents into the cytoplasm. The binding affinity of 2-amino 6-chloro 3 nitropyridine for chloride may be due to hydrogen bonding interactions.
Uses
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.