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196657

Sigma-Aldrich

1-Fluoronaphthalene

99%

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Synonym(s):
α-Fluoronaphthalene
Empirical Formula (Hill Notation):
C10H7F
CAS Number:
Molecular Weight:
146.16
Beilstein/REAXYS Number:
1906413
EC Number:
MDL number:
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.)

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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1 of 4

This Item
190403537195391573
vibrant-m

196657

1-Fluoronaphthalene

vibrant-m

190403

2,3-Dimethyl-1-butene

vibrant-m

537195

1-Bromo-4-fluoronaphthalene

vibrant-m

391573

1-Bromopyrene

assay

99%

assay

97%

assay

97%

assay

96%

mp

−13 °C (lit.)

mp

−158 °C (lit.)

mp

35-38 °C (lit.)

mp

102-105 °C (lit.)

refractive index

n20/D 1.593 (lit.)

refractive index

n20/D 1.389 (lit.)

refractive index

-

refractive index

-

form

liquid

form

liquid

form

-

form

powder

density

1.1322 g/mL at 20 °C (lit.)

density

0.68 g/mL at 25 °C (lit.)

density

-

density

-

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

149.0 °F - closed cup

flash_point_c

65 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Asymmetric synthesis and absolute stereochemistry of LY248686.
Deeter J, et al.
Tetrahedron Letters, 31(49), 7101-7104 (1990)
Formation of O 2 (1Sigma g+) by 1-fluoronaphthalene sensitization.
Andrews LJ and Abrahamson EW.
Chemical Physics Letters, 10, 113-116 (1971)
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
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.

Protocols

US EPA Method 610 describes the analysis of polynuclear aromatic hydrocarbons (commonly referred to as PAHs or PNAs) by both HPLC and GC.

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