Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Organic Chemistry >  Carboxylic acids and derivatives >  Ethyl indole-2-carboxylate

Ethyl indole-2-carboxylate

Basic information Safety Supplier Related

Ethyl indole-2-carboxylate Basic information

Product Name:
Ethyl indole-2-carboxylate
Synonyms:
  • INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
  • ETHYL 2-INDOLECARBOXYLATE
  • ETHYL 1H-INDOLE-2-CARBOXYLATE
  • ETHYL INDOLE-2-CARBOXYLATE
  • 2-CARBETHOXYINDOLE
  • 1H-INDOLE-2-CARBOXYLIC ACID, ETHYL ESTER
  • SPECS AF-966/00545036
  • Ethyl fluoroindole-2-carboxylate
CAS:
3770-50-1
MF:
C11H11NO2
MW:
189.21
EINECS:
223-206-4
Product Categories:
  • Building Blocks
  • C11
  • Building Blocks
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • Heterocycle-Indole series
  • Pharmaceutical Intermediates
  • Esters
  • Pyrroles & Indoles
  • Indole
  • Indoles
  • Simple Indoles
  • Pyrroles & Indoles
  • Heterocyclic Building Blocks
  • Indole/indoline/oxindole
  • Indole and Indoline
  • Indoles and derivatives
Mol File:
3770-50-1.mol
More
Less

Ethyl indole-2-carboxylate Chemical Properties

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
pka
15.01±0.30(Predicted)
form 
Crystals or Crystalline Powder
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
InChIKey
QQXQAEWRSVZPJM-UHFFFAOYSA-N
SMILES
N1C2=C(C=CC=C2)C=C1C(OCC)=O
CAS DataBase Reference
3770-50-1(CAS DataBase Reference)
NIST Chemistry Reference
1H-indole-2-carboxylic acid, ethyl ester(3770-50-1)
More
Less

Safety Information

Safety Statements 
24/25
WGK Germany 
3
Hazard Note 
Keep Cold
HazardClass 
IRRITANT
HS Code 
29339990

MSDS

More
Less

Ethyl indole-2-carboxylate Usage And Synthesis

Chemical Properties

white to yellow crystals or crystalline powder

Uses

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.

Uses

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].

Ethyl indole-2-carboxylateSupplier

Shangqiu Ladybug Network Technology Co., LTD Gold
Tel
0370-2059268 15672839268
Email
2352713635@qq.com
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Email
market03@meryer.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Email
3bsc@sina.com
Alfa Aesar
Tel
400-6106006
Email
saleschina@alfa-asia.com