CAS 611-09-6 5-Nitroisatin (HCID 4669250)

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Basic information

CAS: 611-09-6
Standard SMILES: O=C1Nc2ccc([N+](=O)[O-])cc2C1=O
InChIKey: UNMYHYODJHKLOC-UHFFFAOYSA-N
Molecular formula: C8H4N2O4
Average molar mass: 192.13 g/mol
Monoisotopic mass: 192.01710661

Overview

5-Nitroisatin is a member of indoles. It has a role as an anticoronaviral agent.

Names & identifiers

Preferred name: 5-Nitroisatin
IUPAC: 5-nitro-1H-indole-2,3-dione
English name: 5-Nitroisatin
Molecular formula: C8H4N2O4
Molecular weight: 192.13

Names & synonyms

5-Nitroisatin611-09-65-Nitroindoline-2,3-dione5-Nitro-1H-indole-2,3-dione5-Nitroindole-2,3-dione1H-Indole-2,3-dione, 5-nitro-N-NitroisatinIsatin, 5-nitro-INDOLE-2,3-DIONE, 5-NITRO-5-Nitro-2,3-indolinedioneCCRIS 4031NSC 525798

Show more names

NitroisatinAKOS B0225615-Nitrosotin5-nitro-isati5-Nitroisatin>AKOS BBS-00006405

2,3-Dihydro-5-nitroindole-2,3-dioneDTXSID8049331EINECS 210-252-5BRN 0180223NITROISATIN, 5-J4J633881ZNSC-525798DTXCID3029287

Database identifiers

CAS: 611-09-6
PubChem CID: 4669250
DTXSID: DTXSID8049331
ChEMBL: CHEMBL118305
ChEBI: CHEBI:149791
UNII: J4J633881Z
EC Number: 210-252-5
Nikkaji: J2.990D

Properties

Computed structural properties

XLogP: 0.5
Topological polar surface area: 92 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 309

Experimental & physicochemical properties

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

LogP0.47

Physicochemical properties

Melting point: 251 °C · 251 °C (dec.) (lit.)
Boiling point: 328.09 °C · 328.09°C (rough estimate)
Density: 1.5513 · 1.5513 (rough estimate)
refractive index: 1.49 · 1.4900 (estimate)
storage temp.: Sealed in dry,Room Temperature
form: Crystalline Powder
pka: 8.06 · 8.06±0.20(Predicted)
color: Orange-yellow to orange
BRN: 180223 · 180223
InChI: InChI=1S/C8H4N2O4/c11-7-5-3-4(10(13)14)1-2-6(5)9-8(7)12/h1-3H,(H,9,11,12)
InChIKey: UNMYHYODJHKLOC-UHFFFAOYSA-N

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (90.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (90.9%)

Safety data

PPE: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: NL7970000
ridadr: 2811
hs_code: 29337900
risk_code: 20/21/22-40-68-22
Signal word: Warning
Symbol(GHS): GHS07,GHS08
hazard_code: Xn,Xi
safety_code: 7-22-36/37/39-45-36/37
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H302+H312+H332-H351
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2
Precautionary statements: P202-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313

Chemistry & industry

Applications · 1 item

UsesReactant for preparation of:Potential antibacterial and antifungal agentsspiro[indole-thiazolidinones] as a medicinally important scaffoldPotential antimycobacterial agentsAnticonvulsant agentsInhibitors of human transglutaminase 2Anthelmintic agentsAnti-human immunodeficiency virus (HIV) agentsAntimicrobial agentsPotential antitubercular agentsInhibitors of acetylcholinesterase

Preparation methods · 1 item

PreparationIsatin 30 (14.7 g, 0.1 mol) was added to conc. H2SO4 (121 ml) cooled to 0 ºC in an ice-salt bath. Fuming HNO3 (4.2 ml) was added to this, drop by drop, in such a way that temperature should not rise above 5 ºC. The reaction mixture was allowed to stand for about 30 minutes and then poured over crushed ice (500 g). A yellow precipitate separated immediately. The 5-Nitroisatin was filtered and washed with water and air dried to a constant weight (15 g). Yield : 85%