321-38-0

Basic information

• Product Name: 1-Fluoronaphthalene
• Synonyms: 1-Fluornaftalen;1-fluoro-naphthalen;alpha-Fluoronaphthalene;1-FLUORONAPHTHALENE;1-FLUORONAPTHALENE;Fluoronaphthalene;1-FLUORONAPHTHALENE, 1000MG, NEAT;I-Fluoronaphthalene
• CAS NO: 321-38-0
• Molecular Formula: C₁₀H₇F
• Molecular Weight: 146.16
• EINECS: 206-287-0
• Product Categories: Other fluorin-contained compounds;Miscellaneous;Alpha Sort;E-LAlphabetic;F;FA - FLChemical Class;FluoroAnalytical Standards;Naphthalenes;Volatiles/ Semivolatiles;Method 625EPA;600 Series Wastewater Methods;8000 Series Solidwaste Methods;Chemical Class;FluoroEPA;Halogenated;Method 8100;Aryl;C9 to C12;Halogenated Hydrocarbons;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Fluorine series;Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 321-38-0.mol

Chemical Properties

• Melting Point: −13 °C(lit.)
• Boiling Point: 215 °C(lit.)
• Flash Point: 150 °F
• Appearance: clear slightly yellow to yellow-brown liquid
• Density: 1.1322 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0392mmHg at 25°C
• Refractive Index: n20/D 1.593(lit.)
• Storage Temp.: room temp
• Solubility: slightly soluble in water, well soluble in chloroform, ethyl acetate, and methanol.
• Water Solubility: Not miscible or difficult to mix in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1906413
• CAS DataBase Reference: 1-Fluoronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Fluoronaphthalene(321-38-0)
• EPA Substance Registry System: 1-Fluoronaphthalene(321-38-0)

Safety Data

• Hazard Codes: Xi,F,T,Xn
• Statements: 36/37/38-63-43-23/24/25-45-40
• Safety Statements: 26-36-36/37-24/25-23-53
• RIDADR: UN 2810
• WGK Germany: 3
• RTECS: QJ7100000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 321-38-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Fluoronaphthalene is used as a pharmaceutical intermediate for its role in the synthesis of various drugs. It serves as a key component in the production of LY248686, a potent inhibitor of serotonin and norepinephrine uptake, which is beneficial for the development of medications targeting mood disorders and other related conditions.
Used in Chemical Synthesis:
1-Fluoronaphthalene is used as a starting material or intermediate in the synthesis of various organic compounds, such as 6-substituted phenanthridines. This application is particularly relevant in the field of organic chemistry, where it contributes to the development of new molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
As a fluorinated naphthalene derivative, 1-Fluoronaphthalene is utilized in research and development for the study of its chemical properties, reactivity, and potential applications in various fields. Its unique structure and properties make it an interesting compound for scientists to explore and develop new methodologies and applications.

Preparation

The preparation of 1-Fluoronaphthalene is as follows:1) Diazotization reaction: 1500 g of hydrochloric acid (mass concentration: 25%) and 300 g of naphthylamine were added to a 3000 mL three-necked flask, stirred and heated to 75 ° C to dissolve, and the temperature was lowered to below 5 ° C, and 148 g was slowly added at this temperature. Sodium nitrite, stirred at low temperature for 0.3 hours after the addition, to obtain a diazonium salt solution;2) Substitution reaction: 360 g of fluoroboric acid solution (concentration: 45%) was added to the resulting solution obtained in the step 1), stirred for 0.25 h, filtered, and the filter cake was dried at a temperature of 50 ° C for 0.2 h to obtain Dry naphthylamine diazonium salt fluoroborate double salt;3) Hot air decomposition: the dried diazonium salt fluoroborate double salt is slowly added to the reactor through which hot air (hot air temperature is 85-90 ° C), and the dried powdered naphthylamine diazonium salt fluoroborate double salt is The hot air blows up the dispersion and absorbs the heat for thermal decomposition to obtain a 1-fluoronaphthalene solution containing a small amount of solid impurities;4) Purification treatment: the 1-fluoronaphthalene solution obtained in the step 3) is first washed with pure water for 3 to 6 times, then neutralized with a soda ash to a pH of 6.8 to 7.2, and finally the oil layer is separated by filtration, and the filtrate is taken. The distillation treatment gave 210 g of a naphthalene-based fluorine-containing intermediate 1-fluoronaphthalene in an amount of 99.8%.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Simple aromatic halogenated organic compounds, such as Fluoronaphthalene, are very unreactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

InChI:InChI=1/C12H9F/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H

Upstream product

• 134-32-7 1-amino-naphthalene 
• 28912-93-8 1-naphthyldiazonium tetrafluoroborate 
• 91-20-3 naphthalene 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 4780-79-4 1-naphthalene methanol 
• 18052-80-7 1-naphthyltrimethylsilane 
• 394-61-6 1-fluoronaphthalene - picric acid complex 
• 130490-59-4 [1]naphthyl lead ⁽³⁺⁾; triacetate 
• 703-55-9 1-naphthylmagnesiumbromide 
• 642-28-4 phenyl(1-naphthyl)methanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 67-56-1 methanol 
• 14474-59-0 naphthalen-1-yl-lithium 
• 3759-61-3 1-naphthyl chloroformate 

Downstream Products

• 62062-39-9 1-naphthalen-1-yl-piperidine 
• 5465-85-0 N-(2-naphthyl)piperidine 
• 91-20-3 naphthalene 
• 84-95-7 N,N-diethyl-1-naphthylamine 
• 13672-17-8 N,N-diethylnaphthalen-2-amine 
• 315-99-1 2-fluoro-1-(4-fluoro-[1]naphthyl)-ethanone 
• 341-41-3 1-bromo-4-fluoronaphthalene 
• 341-92-4 1-fluoro-4-nitronaphthalene 
• 316-69-8 4-fluoro-naphthalene-1-sulfonyl chloride 
• 317-79-3 2-bromo-1-fluoronaphthalene 
• 3094-25-5 1-(chloromethyl)-4-fluoronaphthalene 
• 612-94-2 2-phenylnaphthalene 
• 605-02-7 1-phenylnaphthalene 
• 108981-94-8 2-phenyl-1-naphthalenecarboxylic acid 

Relevant articles and documents

Solvent effects in the fluorination of aromatic molecules with 'F-TEDA-BF4'

The type of functionalization of an aromatic molecule achieved with 1-chloro-4-fluoro-1,4-diazobicyclo-(2,2,2)octane bis-tetrafluoroborate, 'F-TEDA-BF4', in trifluoroacetic acid depends on its structure: naphthalene and phenanthrene gave fluorinated products, anthracene gave the trifluoroacetate, while an addition process occurred with 9-methoxy-phenanthrene in methanol, and an addition-elimination process in trifluoroacetic acid. - Keywords: Solvent effects; Fluorination; Aromate molecules; F-TEDA-BF4; Structural effects; Addition processes

Ruthenium-catalyzed nucleophilic fluorination of halobenzenes

The first π-coordination-catalyzed nucleophilic fluorination of unactivated aryl halides has been demonstrated. Chlorobenzene reacts with alkali metal fluorides (CsF, KF) in the presence of a Cp?Ru catalyst at 120-180°C to give fluorobenzene.

Preparation method of 1-fluoronaphthalene

The invention provides a preparation method of 1-fluoronaphthalene. The preparation method comprises: mixing 1-naphthylamine, a strong acid solution and a nitrite solution/nitrite ester, and carrying out a diazotization reaction to obtain a diazonium salt solution; mixing the diazonium salt solution with a fluorine-containing compound, and separating out salt to obtain diazonium salt, wherein the fluorine-containing compound is fluoboric acid, fluorophosphoric acid, fluoborate or fluorophosphate; mixing the diazonium salt with a solvent and a fluoride salt, and conducting cracking to obtain a 1-fluoronaphthalene crude product solution; and purifying the 1-fluoronaphthalene crude product solution to obtain 1-fluoronaphthalene. According to the method, 1-naphthylamine is taken as a raw material, and diazotization reaction is conducted on the 1-naphthylamine and nitrite in an acid environment to obtain a diazonium salt solution; then reaction with BF4 or PF6 in a fluorine-containing compound is conducted for salt precipitation, the obtained diazonium salt is cracked under the action of F, and a byproduct is converted into fluoborate or fluorophosphate, so that the yield of high-toxicity boron trifluoride and phosphorus fluoride is reduced, and the reaction safety is improved.

Naphthalene-based fluorine-containing intermediate 1-fluoronaphthalene synthesis method

The invention discloses a naphthalene-based fluorine-containing intermediate 1-fluoronaphthalene synthesis method, which comprises: 1) diazotization reaction: mixing alpha-naphthylamine and a hydrochloric acid solution, adding sodium nitrite, and carrying out a diazotization reaction to obtain a diazonium salt solution; 2) substitution reaction: adding fluoroboric acid to the diazonium salt solution, carrying out a substitution reaction, and sequentially carrying out filtering and drying on the solid phase product after the reaction to obtain an alpha-naphthylamine-diazonium salt-fluoroboric acid compound salt; 3) hot air decomposition: carrying out hot air decomposition on the alpha-naphthylamine-diazonium salt-fluoroboric acid compound salt to obtain a 1-fluoronaphthalene solution; and 4) purification treatment: purifying the 1-fluoronaphthalene solution to obtain the naphthalene-based fluorine-containing intermediate 1-fluoronaphthalene. According to the present invention, the hot air is used as the heat source, the alpha-naphthylamine-diazonium salt-fluoroboric acid compound salt is decomposed after the alpha-naphthylamine-diazonium salt-fluoroboric acid compound salt absorbs the hot air energy, and the decomposing reaction is stably performed in the hot air flow, such that the reaction process is easily controlled, the reaction process has less dangerous and harmful factors, the safety degree is high, and the flammable and explosive rick sources are eliminated.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction

The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.

Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons

To date, cleavage of the C-N bond in aromatic amides has been achieved in molecules with a distorted constitutional framework around the nitrogen atom. In this report, a nickel-catalyzed reduction of planar amides to the corresponding lower hydrocarbon homologue has been reported. This involves a one-pot reductive cleavage of the C-N bond followed by a tandem C-CO bond break in the presence of a hydride source. Substrate scope circumscribes deamidation examples which proceed via oxidative addition of nickel in the amide bonds of nontwisted amides. Mechanistic studies involving isolation and characterization of involved intermediates via different spectroscopic techniques reveal a deeper introspection into the plausible catalytic cycle for the methodology.

Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates

This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.

PHOSPHORUS-CONTAINING CATALYSTS

The invention provides compounds of general structure I: (Ar1—Ar2—Ar3-E-P(=D)R2-)nMmXnLn″. In this structure: ?Ar1, Ar2 and Ar3 are aromatic groups wherein: —Ar1 and Ar3 are in a 1,3 relationship on Ar2, —each of Ar1, Ar2 and Ar3 optionally comprises one or more ring substituents of formula YR′r wherein each Y independently is absent or is O, S, B, N or Si and each R′ is independently H, halogen, alkyl, cycloalkyl, aryl or heteroaryl and r is 1, 2 or 3, where r is 1 if Y is absent or is O or S, 2 if Y is B or N and 3 if Y is Si, —Ar1, Ar2 and Ar3 are each independently carbocyclic or heterocyclic and each is independently monocyclic, bicyclic or polycyclic and each ring of each of Ar1, Ar2 and Ar3 independently has 5, 6 or 7 ring atoms; ?E is absent or is selected from the group consisting of O, S, NR″, SiR″2, AsR″2 and CR″2; ?M is a complexing metal; ?X is selected from the group consisting of H, F, Br, CI, I, OTf, dba (dibenzylidene acetone), OC(═O)CF3 and OAc; ?L is selected from the group consisting of PR″2, NR″2, OR″, SR″, SiR″3, AsR″3, alkene, alkyne, aryl and heteroaryl, each of said alkene, alkyne, aryl and heteroaryl being optionally substituted, for example with one or more halogens and/or with one or more R groups as defined herein; ?each R is independently alkyl, cycloalkyl, heterocyclyl, heterocycloalkyl, aryl or -, heteroaryl; ?D is absent or is ═S or —O or —Z-linker-Z—, where each Z independently is O or NH or N-alkyl and linker is an alkyl chain of 2-5 carbon atoms in length; ?each R″ is independently H, alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl, each other than H being optionally substituted, or R″2 is —Z-linker-Z— as defined above; and ?m is 0 or 1 or 2; wherein if m is 0, n is 1, n′ and n″ are 0 and -- is absent; and if m is 1 or 2, n is 1 or 2 and n′ and n″ are integers such that the coordination sphere of M is filled, and D is absent.

METAL OXIDE CATALYZED RADIOFLUORINATION

Inter alia, the first titania-catalyzed [18F]-radiofluorination in highly aqueous medium is provided. In embodiments, the method utilizes titanium dioxide, 1 : 1 acetonitrile- thexyl alcohol solvent mixture and tetrabutylammonium bicarbonate as a base. Radiolabeling may be directly performed with aqueous [18F]fluoride without the need for drying/azeotroping step, which reduces radiosynthesis time while keeping high fluoride conversion. The general applicability of the synthetic strategy to the synthesis of the wide range of PET probes from tosylated precursors is demonstrated.