Ethyl 7-nitroindole-2-carboxylate Chemical Properties

Melting point:

90-96 °C

Boiling point:

376.52°C (rough estimate)

Density 

1.3240 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

2-8°C

pka

11.98±0.30(Predicted)

form 

Solid

Appearance

Light yellow to yellow Solid

Water Solubility 

Negligible

InChI

InChI=1S/C11H10N2O4/c1-2-17-11(14)8-6-7-4-3-5-9(13(15)16)10(7)12-8/h3-6,12H,2H2,1H3

InChIKey

GTZAIVBXGPLYGD-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2[N+]([O-])=O)C=C1C(OCC)=O

CAS DataBase Reference

6960-46-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

Hazard Note 

Irritant

HS Code 

29339980

MSDS

• Language:English Provider:ACROS

Ethyl 7-nitroindole-2-carboxylate Usage And Synthesis

Chemical Properties

yellow to brown powder

Uses

Ethyl 7-Nitroindole-2-carboxylate is used to prepare aryl(indolyl)oxadiazoles via Fischer indole synthesis of pyruvate nitrophenylhydrazones. It is also used to synthesize p38 Inhibitors.

Synthesis

Example 2: Synthesis of ethyl 7-nitro-1H-indole-2-carboxylate In a 250 mL three-neck flask, dry Compounds 1a and 1b (12.00 g, 47.76 mmol) and polyphosphoric acid (64.56 g, 191.05 mmol) were added. The mixture was heated to 70 °C with thorough stirring, followed by warming to 80 °C for 12 h of reaction. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the viscous black reaction solution was slowly poured into cold water (400 g) while it was still hot and stirred until the polyphosphoric acid was completely hydrolyzed. At this point, the solution was black in color and a brown-black solid precipitated. The solid was collected by filtration and dried. The dried brown-black solid was extracted continuously for 12 h using Soxhlet extraction method with petroleum ether (boiling point 60-90 °C) as solvent. After completion of extraction, the petroleum ether solution was concentrated to give a yellow solid. Further by ethanol recrystallization, needle-like yellow crystals were obtained, i.e., the target product ethyl 7-nitro-1H-indole-2-carboxylate (10.5 g, 94% yield). Product characterization: Melting point: 92-93°C (literature value: 91-93°C); 1H NMR (200 MHz, CDCl3) δ: 1.41 (t, J = 7.2 Hz, 3H, CH3), 4.42 (q, J = 7.2 Hz, 2H, CH2), 7.20 (t, J = 7.9 Hz, 1H, ArH), 7.28 (d, J = 2.1 Hz, 1H, ArH), 7.97 (d, J = 7.8 Hz, 1H , ArH), 8.21 (d, J = 8.0 Hz, 1H, ArH), 10.25 (s, 1H, NH). 13C NMR (50 MHz, CDCl3) δ: 14.8, 62.0, 109.7, 120.5, 122.6, 130.0, 130.6, 131.1, 131.3, 133.8, 161.1; MS (EI) m/z. MS (EI) m/z: 235 (M+1, 100%), 234 (M+, 69%), 189 (M-45, 38%).

References

[1] Patent: EP2366687, 2011, A2. Location in patent: Page/Page column 8-10
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 6, p. 1850 - 1862
[3] Patent: CN107098846, 2017, A. Location in patent: Paragraph 2633; 2640-2642
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 4621
[5] Journal of Organic Chemistry, 1957, vol. 22, p. 84

Ethyl 7-nitroindole-2-carboxylate(6960-46-9)Related Product Information

• RESMETHRIN
• Triethyl orthoformate
• Ethyl cyanoformate
• Ethylbenzene
• Ethyl acetate
• Ethanol
• Ethyl acrylate
• Ethyl propionate
• 7-Nitroindole
• Ethylparaben
• Urethane
• Ethyl formate
• Ethyl chloroformate
• 7-Nitroindole-2-carboxylic acid
• 7-Aminoindole
• ETHYL 5-NITROINDOLE-2-CARBOXYLATE
• Diethyl ether
• ETHYL 3-(2-CARBOXY-VINYL)-7-NITRO-1H-INDOLE-2-CARBOXYLATE