4-Bromo-1-indanone Chemical Properties

Melting point:

95-99 °C(lit.)

Boiling point:

125°C/1.5mmHg(lit.)

Density 

1.608±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

Orange-brown

InChI

InChI=1S/C9H7BrO/c10-8-3-1-2-7-6(8)4-5-9(7)11/h1-3H,4-5H2

InChIKey

UVVYFYLSZIMKMC-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(Br)=CC=C2)CC1

CAS DataBase Reference

15115-60-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-60-36

WGK Germany 

2

RTECS 

NK7536100

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich

4-Bromo-1-indanone Usage And Synthesis

Chemical Properties

Orange-brown crystalline powder

Uses

4-Bromo-1-indanone is used to prepare N''-indanyl-N-benzopyrazolyl ureas as TRPV1 antagonists for use as analgesics. It is also used to synthesize 1,4-dihydroindeno[1,2-c]pyrazoles as KDR kinase inhibitors.

General Description

4-Bromo-1-indanone is an organic synthetic or pharmaceutical intermediate compound that can be used to prepare the prescription drug Ozanimod. Ozanimod can be used to treat relapsing multiple sclerosis (MS), including clinical solitary syndrome, relapsing-remitting disease and active secondary progressive disease. This drug cannot cure multiple sclerosis, but it can slow down some disabling effects and reduce the frequency of disease recurrence. It can also be used to treat moderate to severe ulcerative colitis.

Synthesis

General procedure for the synthesis of 4-bromoinden-1-one from 3-(2-bromophenyl)propionic acid: trifluoromethanesulfonic acid (3 equiv.) was slowly added dropwise at 0 °C to an anhydrous dichloromethane (1.0 mL) solution of 3-(2-bromophenyl)propionic acid (0.5 mmol) which was placed in a 12 mL Q-tube?pressure tube (provided by QLabtech). Subsequently, the reaction mixture was warmed to room temperature. A PTFE septum was placed on top of the reaction tube and sealed using the appropriate cap and pressure adapter. The sealed reaction tube was heated in an oil bath at 80°C. The progress of the reaction was monitored by thin layer chromatography (TLC) and gas chromatography-mass spectrometry (GC/MS) until the reactants completely disappeared. After completion of the reaction, the mixture was poured into ice water and extracted three times with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Finally, the target compound 4-bromoinden-1-one was isolated and purified from the crude product by fast column chromatography.

References

[1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] Patent: WO2018/106636, 2018, A1. Location in patent: Paragraph 100231
[3] Patent: US2015/25205, 2015, A1. Location in patent: Page/Page column
[4] Patent: WO2015/95188, 2015, A1. Location in patent: Paragraph 00161
[5] Patent: WO2003/99795, 2003, A1. Location in patent: Page 111

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