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196657

Sigma-Aldrich

1-Fluoronaphthalene

99%

Synonym(s):

α-Fluoronaphthalene

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About This Item

Empirical Formula (Hill Notation):
C10H7F
CAS Number:
321-38-0
Molecular Weight:
146.16
Beilstein:
1906413
EC Number:
206-287-0
MDL number:
MFCD00003873
UNSPSC Code:
12352100
PubChem Substance ID:
24851780
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.)

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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