1-Fluoronaphthalene Property

Melting point:

-13 °C (lit.)

Boiling point:

215 °C (lit.)

Density 

1.1322 g/mL at 20 °C (lit.)

refractive index 

n20/D 1.593(lit.)

Flash point:

150 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

slightly soluble in water, well soluble in chloroform, ethyl acetate, and methanol.

form 

Oil

color 

Colourless to Yellow

Specific Gravity

1.332

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

1906413

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

CWLKTJOTWITYSI-UHFFFAOYSA-N

CAS DataBase Reference

321-38-0(CAS DataBase Reference)

NIST Chemistry Reference

Naphthalene, 1-fluoro-(321-38-0)

EPA Substance Registry System

1-Fluoronaphthalene (321-38-0)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN2810

WGK Germany 

3

RTECS 

QJ7100000

Hazard Note 

Flammable

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Fluoronaphthalene Chemical Properties,Usage,Production

Chemical Properties

clear slightly yellow to yellow-brown liquid

Uses

1-Fluoronaphthalene is a fluorinated naphthalene derivative that is metabolized by fungal monooxygenase-epoxide hydrolase. It is also used as a pharmaceutical intermediate. It is Duloxetine impurity.

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.

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.