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HomeProduct name listEthyl indole-2-carboxylate

Ethyl indole-2-carboxylate

Synonym(s):2-Ethoxycarbonylindole;NSC 10076

  • CAS NO.:3770-50-1
  • Empirical Formula: C11H11NO2
  • Molecular Weight: 189.21
  • MDL number: MFCD00005609
  • EINECS: 223-206-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-11 15:28:25
Ethyl indole-2-carboxylate Structural

What is Ethyl indole-2-carboxylate?

Chemical properties

white to yellow crystals or crystalline powder

The Uses of Ethyl indole-2-carboxylate

Reactant for preparation of:• ;CRTH2 receptor antagonists1• ;Indoleamine 2,3-dioxygenase (IDO) inhibitors2• ;Cannabinoid CB1 receptor antagonists3• ;Inhibitors of Human Reticulocyte 15-Lipoxygenase-14• ;N-(benzoylphenyl)-1H-indole-2-carboxamides as potent antihypertriglyceridemic agents5• ;A antiproliferative agent against human leukemia K562 cells6• ;Inhibitors of p38 MAP kinase7• ;Acetolactate synthase inhibitors8

The Uses of Ethyl indole-2-carboxylate

Reactant for preparation of:CRTH2 receptor antagonists;Indoleamine 2,3-dioxygenase (IDO) inhibitors;Cannabinoid CB1 receptor antagonists; Inhibitors of Human Reticulocyte 15-Lipoxygenase-1;N-(benzoylphenyl)-1H-indole-2-carboxamides as potent antihypertriglyceridemic agents;A antiproliferative agent against human leukemia K562 cells;Inhibitors of p38 MAP kinase; Acetolactate synthase inhibitors.

The Uses of Ethyl indole-2-carboxylate

2-Ethoxycarbonylindole is a building block that has been used as a reactant for the preparation of pyridazinoindole derivatives that have antimicrobial activities.

Preparation

Indole-2-carb-oxy-lic acid (0.50 g, 3.1 mmol) was dissolved in SOCl2 (19 ml) at 0°C. After stirring for 1 h, the solution was rotary evaporated, and the resulting oil was added to absolute ethanol (17 ml) at room temperature. After stirring overnight, the solution was vacuum filtered to yield ethyl 1H-indole-2-carboxyl-ate as a beige solid, which was recrystallized from methanol to yield 0.54 g (2.9 mmol, 93%) of the product[1].

References

[1] Will E. Lynch , Clifford W. Padgett, Christine R. Whitlock . “Ethyl 1H-indole-2-carboxyl-ate.” IUCrData 5 (2020): Article x201205.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 39, p. 1152, 1991 DOI: 10.1248/cpb.39.1152

structure and hydrogen bonding

Lynch et al. report the crystal structure of ethyl 1H-indole-2-carboxyl-ate, which forms a hydrogen-bonded dimer. The hydrogen bonding occurs between N atoms of the indole ring and the keto oxygen atoms with an R(10) synthon. The hydrogen bond between N1 and O2i is characterized by an N…O separation of 2.877 Å;, and the ring motifs are placed on inversion centres in the space group P21/c. The crystal structure exhibits a classic herringbone pattern, with the blocks of hydrogen-bonded dimers and the zigzag running along the b-axis direction. The mol-ecule is nearly planar, with a r.m.s.d. of 0.028 Å for the non-hydrogen atoms. No other short contacts or π–π inter-actions are observed in the crystal[1].

Properties of Ethyl indole-2-carboxylate

Melting point: 122-125 °C (lit.)
Boiling point: 324.47°C (rough estimate)
Density  1.1596 (rough estimate)
refractive index  1.5012 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
form  Crystals or Crystalline Powder
pka 15.01±0.30(Predicted)
color  White to yellow
BRN  146395
InChI InChI=1S/C11H11NO2/c1-2-14-11(13)10-7-8-5-3-4-6-9(8)12-10/h3-7,12H,2H2,1H3
CAS DataBase Reference 3770-50-1(CAS DataBase Reference)
NIST Chemistry Reference 1H-indole-2-carboxylic acid, ethyl ester(3770-50-1)

Safety information for Ethyl indole-2-carboxylate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H332:Acute toxicity,inhalation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Ethyl indole-2-carboxylate

InChIKey QQXQAEWRSVZPJM-UHFFFAOYSA-N
SMILES N1C2=C(C=CC=C2)C=C1C(OCC)=O

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