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349593

Sigma-Aldrich

6-Fluoroindole

98%

Synonym(s):

NSC 520436

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About This Item

Empirical Formula (Hill Notation):
C8H6FN
CAS Number:
399-51-9
Molecular Weight:
135.14
Beilstein/REAXYS Number:
112192
MDL number:
MFCD00056933
UNSPSC Code:
12352100
PubChem Substance ID:
24861689
NACRES:
NA.22

Quality Level

100

assay

98%

mp

72-76 °C (lit.)

SMILES string

Fc1ccc2cc[nH]c2c1

InChI

1S/C8H6FN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H

InChI key

YYFFEPUCAKVRJX-UHFFFAOYSA-N

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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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
Na, Y. M.
Bull. Korean Chem. Soc., 31, 3467-3467 (2010)
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
Chun-Hsu Yao et al.
Journal of medicinal chemistry, 54(1), 166-178 (2010-12-07)
A novel series of N-linked β-D-xylosides were synthesized and evaluated for inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) in a cell-based assay. Of these, the 4-chloro-3-(4-cyclopropylbenzyl)-1-(β-D-xylopyranosyl)-1H-indole 19m was found to be the most potent inhibitor, with an EC(50) value
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