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349593 Aldrich

6-Fluoroindole

98%

Synonym: NSC 520436

  • CAS Number 399-51-9

  • Empirical Formula (Hill Notation) C8H6FN

  • Molecular Weight 135.14

  •  Beilstein Registry Number 112192

  •  MDL number MFCD00056933

  •  PubChem Substance ID 24861689

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Description

Packaging

1, 5 g in glass bottle

Application

6-Fluoroindole may be used as reactant in the preparation of:
• tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1
• antibacterial agents2
• antifungal agents3
• Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the management of hyperglycemia in diabetes4
• potent selective serotonin reuptake inhibitors5,6
• inhibitors of HIV-1 attachment7

General description

6-Fluoroindole is a halogen substituted indole. Experimental ionization potential of 6-fluoroindole has been evaluated.8 Preparation of 6-fluoroindole via nitration of indoline has been reported.9

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
3

Protocols & Articles

Peer-Reviewed Papers

References

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1. Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. Dolusic, E.; et al. J. Med. Chem. 54, 5320, (2011)

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2. Synthesis and evaluation of 1-(1H-indol-3-yl)ethanamine derivatives as new antibacterial agents. Burchak, O. N.; et al. Bioorg. Med. Chem. 19, 3204, (2011)

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3. Na, Y. M. Bull. Korean Chem. Soc. 31, 3467, (2010)

4. Discovery of novel N-β-D-xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes. Yao, C.-H.; et al. J. Med. Chem. 54, 166, (2011)

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5. Conformationally restricted homotryptamines. Part 7: 3-cis-(3-aminocyclopentyl)indoles as potent selective serotonin reuptake inhibitors. King, H. D.; et al. J. Med. Chem. 53, 7564, (2010)

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6. Synthesis and structure-affinity relationships of novel small molecule natural product derivatives capable of discriminating between serotonin 5-HT1A, 5-HT2A, 5-HT2C receptor subtypes. Cummings, D. F.; et al. Bioorg. Med. Chem. 18, 4783, (2010)

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7. Meanwell, N., A.; et al. Bioorg. Med. Chem. Lett. 20, 1460, (2010)

8. Ionization potentials of fluoroindoles and the origin of nonexponential tryptophan fluorescence decay in proteins. Liu T, Callis PR, Hesp BH, et al. J. Am. Chem. Soc. 127(11), 4104-13, (2005)

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9. Synthesis of 5-and 6-Halogenoindoles from Indoline Ikan R, et al. Israel J. Chem. 2(2), 37-42, (1964)

J. Med. Chem. 36, 2242, (1993)

3-(2-(3-Pyridinyl)thiazolidin-4-oyl)indoles, a novel series of platelet activating factor antagonists. J. Med. Chem. 37, 2011, (1994)

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New indole derivatives as potent and selective serotonin uptake inhibitors. J. Med. Chem. 36, 1194, (1993)

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Beil. 20,V,7,32

FT-IR 2 (3), 3574:B

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