196657
1-Fluoronaphthalene
99%
Synonym(s):
α-Fluoronaphthalene
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About This Item
Empirical Formula (Hill Notation):
C10H7F
CAS Number:
Molecular Weight:
146.16
Beilstein:
1906413
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
99%
form
liquid
refractive index
n20/D 1.593 (lit.)
bp
215 °C (lit.)
mp
−13 °C (lit.)
density
1.1322 g/mL at 20 °C (lit.)
functional group
fluoro
SMILES string
Fc1cccc2ccccc12
InChI
1S/C10H7F/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
InChI key
CWLKTJOTWITYSI-UHFFFAOYSA-N
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General description
Flash photolysis of O2 and 1-fluoronaphthalene mixtures in the gas phase have been investigated.
Application
1-Fluoronaphthalene was used in t-BuLi-mediated synthesis of 6-substituted phenanthridines. It was also used in the synthesis of LY248686, a potent inhibitor of serotonin and norepinephrine uptake.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
149.0 °F - closed cup
Flash Point(C)
65 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Jan Pawlas et al.
Organic letters, 4(16), 2687-2690 (2002-08-03)
[reaction: see text] A one-pot, t-BuLi-induced synthesis of 6-substituted phenanthridines from fluoroarenes and nitriles via 1,2-arynes is reported. Aryl- and hetaryl nitriles, cyanamides, and trimethylacetonitrile gave phenanthridine products. The method was extended to provide bisphenanthridine 10 by a one-pot bis-cyclization
Formation of O 2 (1Sigma g+) by 1-fluoronaphthalene sensitization.
Andrews LJ and Abrahamson EW.
Chemical Physics Letters, 10, 113-116 (1971)
Asymmetric synthesis and absolute stereochemistry of LY248686.
Deeter J, et al.
Tetrahedron Letters, 31(49), 7101-7104 (1990)
C E Cerniglia et al.
Applied and environmental microbiology, 48(2), 294-300 (1984-08-01)
The metabolism of 1-fluoronaphthalene by Cunninghamella elegans ATCC 36112 was studied. The metabolites were isolated by reverse-phase high-pressure liquid chromatography and characterized by the application of UV absorption, 1H nuclear magnetic resonance, and mass spectral techniques. C. elegans oxidized 1-fluoronaphthalene
Peter Wipf et al.
Organic letters, 5(7), 1155-1158 (2003-03-28)
[reaction: see text] Electron-rich dinaphthyl ethers were synthesized by S(N)Ar reactions between naphthols and activated fluoronaphthalenes. 2-tert-Butyl-1,1,3,3-tetramethylguanidine (Barton's base) was found to be an excellent, mild alternative to traditional inorganic bases for promoting the coupling reaction.
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