Fluoronaphthalene

• CAS: 321-38-0
• Catalog Number: ACM321380
• Category: Main Products
• Molecular Weight: 146.16
• Molecular Formula: C₁₀H₇F
• Synonyms: 1-Fluornaftalen;1-fluoro-naphthalen;alpha-Fluoronaphthalene;1-FLUORONAPHTHALENE;1-FLUORONAPTHALENE;Fluoronaphthalene;1-FLUORONAPHTHALENE, 1000MG, NEAT;I-Fluoronaphthalene
• IUPAC Name: 1-fluoronaphthalene
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2F
• InChI Key: CWLKTJOTWITYSI-UHFFFAOYSA-N
• Boiling Point: 215°C(lit.)
• Melting Point: -13°C(lit.)
• Flash Point: 150°F
• Density: 1.1322g/mL at 20°C(lit.)
• Appearance: Needles.
• EC Number: 206-287-0
• Exact Mass: 146.05300
• Hazard Statements: Xi,F,T,Xn
• RIDADR: NONH for all modes of transport
• Safety Description: 26-36-36/37-24/25-23-53
• Stability: Stable. Incompatible with strong oxidizing agents.
• Supplemental Hazard Statements: H227-H315-H319-H335-H351
• Symbol: GHS07,GHS08
• UN Number: 2810
• WGK Germany: 3

Case Study

Fluoronaphthalene as a candidate for absorption-enhancing component in photoresists

Ikeda, Sadatatsu, et al. Japanese Journal of Applied Physics 49.9R (2010): 096504.

With the reduction of photoresist thickness and miniaturization of feature size, improving the absorption coefficient of extreme ultraviolet (EUV) photoresists has become increasingly important from the perspective of efficient use of incident radiation. Fluorination of photoresist polymers is the most effective method to increase the absorption coefficient. Fluoronaphthalene was used as a possible candidate for suppressing the attachment of dissociative electrons to examine the electron flow in fluorinated photoresists. The molecular structure dependence of the reactivity with solvated electrons of tetrahydrofuran, the electron transfer of fluoronaphthalene radical anions to triphenylsulfonium-trifluoroethylene ester, the dissociation of fluoronaphthalene radical anions, and the charge recombination of fluoronaphthalene radical anions with protons were elucidated by comparing 8-fluoronaphthalene, 1-fluoronaphthalene, and naphthalene. The dissociation rate of fluoronaphthalene radical anions is negligible.
Octafluoronaphthalene (8FN), 1-fluoronaphthalene (1FN), and naphthalene (Nph) were used to elucidate the fluorination effect. TPS-tf was used as an acid generator. THF was used as a liquid matrix for efficient generation of anionic species. Two types of pulsed radiolysis systems were used to observe the kinetics of short-lived intermediates within the time frame of the induced reaction. The pulsed radiolysis experiments were conducted at the Institute of Scientific and Industrial Research, Osaka University. The energy of the electron pulse was 26 MeV. In addition, the effect of naphthalene derivatives on acid generation was investigated by measuring the acid yield generated in poly(4-hydroxystyrene) (PHS) films when exposed to EUV. All experiments were performed at room temperature.

RP-HPLC method for the analysis of 1-fluoronaphthalene

Karagiannidou, Evrykleia G., Eleni T. Bekiari, and Elli I. Vastardi. Journal of Chromatographic Science 53.8 (2015): 1296-1302.

A simple and precise reversed-phase HPLC method was developed and validated for the determination of 1-fluoronaphthalene and its process-related impurities 1-aminonaphthalene, 1-nitronaphthalene, naphthalene and 2-fluoronaphthalene. 1-Fluoronaphthalene is a key starting material for the synthesis of the duloxetine hydrochloride active pharmaceutical ingredient and is therefore a potential impurity of the API. The determination of the impurity profile is essential for the safety assessment of substances and their manufacturing processes. In the duloxetine hydrochloride active pharmaceutical ingredient, only 1-fluoronaphthalene was detected, while its related impurities 1-aminonaphthalene, 1-nitronaphthalene, naphthalene and 2-fluoronaphthalene were not detected. The average recoveries for all investigated impurities were in the range of 90-110%. Due to its specificity, high precision and accuracy, the developed method can be used for the determination of 1-fluoronaphthalene, a key starting material for the synthesis of the duloxetine hydrochloride API.
The flow rate of the mobile phase was 1.0 mL/min. The column temperature was maintained at 208°C and the autosampler temperature was maintained at 58°C. The detection was monitored at 230 nm and the injection volume was 10 mL. 1-Fluoronaphthalene and 1-Fluoronaphthalene were diluted with 50 mL of acetonitrile:water 60:40 v/v to obtain 5 solutions containing 500 mg/mL of 1-Fluoronaphthalene and each process impurity. In addition, 1.0 mL of the stock solutions of 1-aminonaphthalene, 1-nitronaphthalene, naphthalene, and 2-Fluoronaphthalene were diluted to 10 mL with acetonitrile:water 60:40 v/v to obtain solutions containing 50 mg/mL of 1-aminonaphthalene, 1-nitronaphthalene, naphthalene, and 2-Fluoronaphthalene. Accurately weigh 50 mg of 1-fluoronaphthalene and dilute it in 100 mL with acetonitrile:water 60:40 v/v. Pipette 5 mL of solution B into the same 100 mL volumetric flask to obtain a solution containing 500 mg/mL.

Resonant two-photon mass analysis threshold ionization spectra of 1-fluoronaphthalene

Tzeng, Sheng Yuan, et al. Journal of Molecular Spectroscopy 281 (2012): 40-46.

The resonant two-photon mass analysis threshold ionization (MATI) technique was applied to record the cationic spectra of 1-fluoronaphthalene (1FN) and 2-fluoronaphthalene (2FN) by ionization in several intermediate vibrational states. The adiabatic ionization energies of 1FN and 2FN were found to be 66 194 and 66 771 ± 5 cm, respectively. Distinct MATI bands arising from in-plane ring deformations were found at 437, 517, 703, and 779 cm for 1FN; and 286, 455, 494, 764, and 1031 cm for 2FN. The frequencies of these modes are slightly larger than the corresponding frequencies in the vibrational spectra. This indicates that the molecular geometry in the cationic Dstate is slightly higher than that in the neutral S state. Comparison of the present experimental data with those for naphthalene shows that the frequency differences for each mode depend on the vibrational mode, the position of the F atom, and the extent to which the F atom participates in the overall vibration.
The experiments were performed using a laser-based photoionization time-of-flight mass spectrometer described elsewhere. 1-Fluoronaphthalene (1FN) and 2-Fluoronaphthalene (2FN) with a purity of 99% were used without further purification. The samples were heated to about 110 °C to obtain sufficient vapor pressure. The vapor was added to 2-3 bar of helium and expanded into vacuum through a pulse valve with an aperture of 0.15 mm. The two-color resonant two-photon excitation process was initiated by utilizing two independent tunable UV laser systems controlled by a delay/pulse generator. The two counter-propagating laser beams were focused and intersected perpendicularly with the molecular beam 50 mm downstream of the nozzle orifice.

Reaction of metal ions with fluoronaphthalene in the gas phase

Bjarnason, Asgeir, and Ben S. Freiser. Rapid Communications in Mass Spectrometry 8.5 (1994): 366-370.

Ti+, V+, Fe+, Co+, and Ni+ with fluoronaphthalene were studied in a Fourier transform mass spectrometer. Sc+, Ti+, V+, and Fe+ were found to defluorinate hydrocarbons in a sequential manner of up to three neutral fluoronaphthalene molecules to form ions. Sc+ was also able to eliminate C2H2 from fluoronaphthalene, showing unusual reactivity, and Ti+ was found to eliminate one hydrogen atom. Secondary and higher order reactions were studied, and several ionic products from primary and secondary reactions were studied by collision induced dissociation. The formation of unmetallated ions was also observed.
The metal ions were produced using a laser desorption method and then monitored for reactions with fluoronaphthalene, which was present at static pressure in the cell of the mass spectrometer. Sc+, Ti+, and V+ were produced by laser desorption of pure metals, and Fe+ and Ni+ were produced from stainless steel; but Co+ was produced by laser desorption of chloride salts rather than pure metals, because metals are ferromagnetic. All reaction pathways were confirmed using double resonance techniques. Argon or nitrogen buffer gas, maintained at 40-100 times the sample gas pressure, was used for repeated experiments to minimize the abundance of "hot" metal ions.

Custom Q&A

What is the molecular formula of fluoronaphthalene?

The molecular formula of fluoronaphthalene is C10H7F.

What is the molecular weight of fluoronaphthalene?

The molecular weight of fluoronaphthalene is 146.16 g/mol.

What is the IUPAC name of fluoronaphthalene?

The IUPAC name of fluoronaphthalene is 1-fluoronaphthalene.

What is the InChIKey of fluoronaphthalene?

The InChIKey of fluoronaphthalene is CWLKTJOTWITYSI-UHFFFAOYSA-N.

What is the CAS number of fluoronaphthalene?

The CAS number of fluoronaphthalene is 321-38-0.

What is the UNII of fluoronaphthalene?

The UNII of fluoronaphthalene is 0920702UT7.

What is the UN number of fluoronaphthalene?

The UN number of fluoronaphthalene is 2810.

How many hydrogen bond donor counts does fluoronaphthalene have?

Fluoronaphthalene has 0 hydrogen bond donor counts.

How many rotatable bond counts does fluoronaphthalene have?

Fluoronaphthalene has 0 rotatable bond counts.