349593
6-Fluoroindole
98%
Synonym(s):
NSC 520436
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About This Item
Empirical Formula (Hill Notation):
C8H6FN
CAS Number:
Molecular Weight:
135.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
112192
Assay:
98%
InChI
1S/C8H6FN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H
SMILES string
Fc1ccc2cc[nH]c2c1
InChI key
YYFFEPUCAKVRJX-UHFFFAOYSA-N
assay
98%
Quality Level
functional group
fluoro
General description
6-Fluoroindole is a halogen substituted indole. Experimental ionization potential of 6-fluoroindole has been evaluated. Preparation of 6-fluoroindole via nitration of indoline has been reported.
Application
6-Fluoroindole may be used as reactant in the preparation of:
- tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- antibacterial agents
- antifungal agents
- Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the management of hyperglycemia in diabetes
- potent selective serotonin reuptake inhibitors
- inhibitors of HIV-1 attachment
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Synthesis of 5-and 6-Halogenoindoles from Indoline
Ikan R, et al.
Israel J. Chem., 2(2), 37-42 (1964)
Journal of Medicinal Chemistry, 36, 2242-2242 (1993)
S Jimmy Budiardjo et al.
ACS synthetic biology, 5(12), 1475-1484 (2016-07-09)
Chemical biology has long sought to build protein switches for use in molecular diagnostics, imaging, and synthetic biology. The overarching challenge for any type of engineered protein switch is the ability to respond in a selective and predictable manner that
David F Cummings et al.
Bioorganic & medicinal chemistry, 18(13), 4783-4792 (2010-06-24)
Efforts to develop ligands that distinguish between clinically relevant 5-HT2A and 5-HT2C serotonin receptor subtypes have been challenging, because their sequences have high homology. Previous studies reported that a novel aplysinopsin belonging to a chemical class of natural products isolated
G S Sheppard et al.
Journal of medicinal chemistry, 37(13), 2011-2032 (1994-06-24)
(2RS,4R)-3-(2-(3-Pyridinyl)thiazolidin-4-oyl)indoles represent a new class of potent, orally active antagonists of platelet activating factor (PAF). The compounds were prepared by acylation of the magnesium or zinc salts of substituted indoles with (2RS,4R)-2-(3-pyridinyl)-3-(tert-butoxycarbonyl)thiazolidin-4-oyl chloride. The 3-acylindole moiety functions as a hydrolytically
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