5-Bromoindole-2-carboxylic acid Chemical Properties

Melting point:

287-288

Boiling point:

470.9±25.0 °C(Predicted)

Density 

1.838±0.06 g/cm3(Predicted)

storage temp. 

-20°C

pka

4.25±0.30(Predicted)

form 

Solid

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H6BrNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13)

InChIKey

YAULOOYNCJDPPU-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Br)C=C2)C=C1C(O)=O

CAS DataBase Reference

7254-19-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich

5-Bromoindole-2-carboxylic acid Usage And Synthesis

Uses

Reactant involved in studies of biologically active molecules including:

• Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases
• Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors
• cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors
• Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors
• Preparation of dual PPARγ/δ agonists
• Synthesis of chemical probes to examine the role of hFPRL1 receptor in inflammation

Uses

5-Bromoindole-2-carboxylic acid,Reactant involved in studies of biologically active molecules including:Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases1;Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors2 ;cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors3 ;Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors4 ;Preparation of dual PPARγ/δ agonists5;Synthesis of chemical probes to examine the role of hFPRL1 receptor .

Synthesis

The general procedure for the synthesis of 5-bromoindole-2-carboxylic acid from ethyl 5-bromoindole-2-carboxylate was as follows: 134 g of ethyl 5-bromoindole-2-carboxylate was dissolved in a solvent mixture of 31.25 g of 96% methanol and 183 mL of water, and was heated and refluxed for 0.5 h. The reaction was completed with the addition of 10% hydrochloric acid. After completion of the reaction, it was cooled to 40 °C and the pH was adjusted to 3-4 by slowly adding 10% hydrochloric acid solution.Subsequently, the reaction mixture was filtered to give 109.1 g of off-white solid 5-bromoindole-2-carboxylic acid in 91% yield, which was analyzed by high-performance liquid chromatography (HPLC) and showed ≥96% purity.

References

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7512 - 7527
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0050; 0053

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