| Identification | More | [Name]
4-Bromo-1-indanone | [CAS]
15115-60-3 | [Synonyms]
4-BROMO-1-INDANONE
4-BROMO-INDAN-1-ONE
4-bromo-1-indanon
4-BROMO-2,3-DIHYDRO-1H-INDEN-1-ONE
4-BROMO-1-INDANONE HPLC 97%
4-bromo-2,3-dihydroinden-1-one | [EINECS(EC#)]
628-019-5 | [Molecular Formula]
C9H7BrO | [MDL Number]
MFCD01719772 | [Molecular Weight]
211.06 | [MOL File]
15115-60-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Orange-brown crystalline powder | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S22:Do not breathe dust . | [WGK Germany ]
2
| [RTECS ]
NK7536100
| [HS Code ]
29147000 |
| Hazard Information | Back Directory | [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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