Ethyl 5-nitro-1H-indole-2-carboxylate

HCID 280312CAS 16732-57-3

Substructure search Find similar structures

Basic information

Standard SMILES: CCOC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]1
InChIKey: DVFJMQCNICEPAI-UHFFFAOYSA-N
Molecular formula: C11H10N2O4
Average molar mass: 234.21 g/mol
Monoisotopic mass: 234.0640568

Names & identifiers

Preferred name: Ethyl 5-nitro-1H-indole-2-carboxylate
IUPAC: ethyl 5-nitro-1H-indole-2-carboxylate
English name: Ethyl 5-nitroindole-2-carboxylate
Molecular formula: C11H10N2O4
Molecular weight: 234.21

Names & synonyms

ethyl 5-nitro-1H-indole-2-carboxylateRefChem:595826674-199-3ethyl 5-nitroindole-2-carboxylate16732-57-35-nitroindole-2-carboxylic acid ethyl esterMFCD00216477ethyl-5-nitroindole-2-carboxylate1H-Indole-2-carboxylic acid, 5-nitro-, ethyl esterSCHEMBL6561562-Ethoxycarbonyl-5-nitroindoleethyl 5-nitro-2-indolecarboxylate

Show more names

OXALIC ACID MONO-(N-METHYL)-AMIDELABOTEST-BB LT004412915-Nitroindole-2-Carboxylic5-Nitroindole-2-carboxylateETHYL 5-NITRO-2-CARBOXYLATEEthyl 5-Nitro Indole-2-Carbonateethyl-5-nitro-1h-indole-carboxylate2-(Ethoxycarbonyl)-5-nitro-1H-indole

AC-7290E11765-Nitro-1H-indole-2-carboxylic acid ethyl esterNSC131897Oprea1_174962SCHEMBL8409653DTXSID80299657DVFJMQCNICEPAI-UHFFFAOYSA-N

Database identifiers

CAS: 16732-57-3
PubChem CID: 280312
DTXSID: DTXSID80299657
EC Number: 674-199-3
Nikkaji: J769.703A

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 87.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 17
Formal charge: 0
Complexity: 315

Physicochemical properties

Melting point: 220 · 220-225 °C
Boiling point: 376.52 °C · 376.52°C (rough estimate)
Density: 1.324 · 1.3240 (rough estimate)
refractive index: 1.53 · 1.5300 (estimate)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
form: Powder
pka: 13.26 · 13.26±0.30(Predicted)
color: Yellow to brown
Water Solubility: negligible
CAS DataBase Reference: 16732 · 16732-57-3(CAS DataBase Reference)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38-41-36
Safety Statements: 24 · 24/25-39-26
HazardClass: IRRITANT
HS Code: 29349990 · 29349990

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H315 (80%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (80%)

Safety data

hs_code: 29349990
risk_code: 36/37/38-41-36
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 24/25-39-26
hazard_class: IRRITANT
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 2 items

UsesEthyl 5-Nitroindole-2-carboxylate is used as a reagent in the synthesis of indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors. Ethyl 5-Nitroindole-2-carboxylate is also a useful synthetic intermediate in the synthesis of Delavirdine which is a bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.

UsesEthyl 5-Nitroindole-2-carboxylate is used as a reagent in the synthesis of indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors. Ethyl 5-Nitroindole-2-carboxylate is also a useful synthetic intermediate in the synthesis of Delavirdine (D230625) which is a bisheteroarylpiperazine (BHAP) reverse transcriptase inhibitor.