1-Fluoronaphthalene

1-Fluoronaphthalene Chemical Properties
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.)
Fp 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 Gravity1.332
Water Solubility Not miscible or difficult to mix in water.
BRN 1906413
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyCWLKTJOTWITYSI-UHFFFAOYSA-N
CAS DataBase Reference321-38-0(CAS DataBase Reference)
NIST Chemistry ReferenceNaphthalene, 1-fluoro-(321-38-0)
EPA Substance Registry System1-Fluoronaphthalene (321-38-0)
Safety Information
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
MSDS Information
ProviderLanguage
Fluoronaphthalene English
SigmaAldrich English
ACROS English
ALFA English
1-Fluoronaphthalene Usage And Synthesis
Chemical Propertiesclear slightly yellow to yellow-brown liquid
Uses1-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.
Application1-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.
PreparationThe 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%.

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Air & Water ReactionsInsoluble in water.
Reactivity ProfileSimple 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.
1-Fluoronaphthalene Preparation Products And Raw materials
Preparation Products4-Fluoronaphtalene-1-boronic acid-->2-(1-FLUORONAPHTHALEN-4-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->(R)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine-->Duloxetine-->3-Bromo-1-fluoronaphthalene-->(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine-->2-(1-NAPHTHYLENE)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE-->1-fluoro-2-iodonaphthalene-->4-FLUORONAPHTHALENE-1-SULFONYL CHLORIDE-->(S)-N,N-DIMETHYL-[3-(2-THIENYL)-3-(1-NAPHTHYLOXY)PROPYL]AMINE--PHOSPHORIC ACID (1:1)-->3-Bromo-1-fluoro-2-iodonaphthalene-->(S)-N,N-DIMETHYL-[3-(2-THIENYL)-3-(1-NAPHTHYLOXY)PROPYL]AMINE--PHOSPHORIC ACID (1:1)-->Duloxetine Impurity 4
4-FLUORO-1-NAPHTHOIC ACID 9-fluorophenanthrene ALPHA-HYDROXY HEPTAFLUORONAPHTHALENE 4-FLUORO-1-NAPHTHYLMAGNESIUM BROMIDE 4-fluorobenzo(j)fluoranthene 1-ACETYL-4-FLUORONAPHTHALENE, 97% 4-FLUORONAPHTHALENE-1-BORONIC ACID,4-Fluoronaphthalene-1-boronic acid ,98% 1,2,3,4-TETRAFLUORO-5-METHOXY-NAPHTHALENE BUTTPARK 34\09-43 12-fluoro-5-methylchrysene HEPTAFLUORO-2-NAPHTHOL 4-FLUORONAPHTHALENE-1-SULFONYL CHLORIDE,4-FLUORONAPHTHALENE-1-SULPHONYL CHLORIDE 1-Bromo-4-fluoronaphthalene 98%,1-Bromo-4-fluoronaphthalene,98%,1-BROMO-4-FLUORONAPHTHALENE BUTTPARK 34\09-31 BUTTPARK 27\09-02 1-Fluoronaphthalene PERFLUOROACENAPHTHYLENE Octafluoronaphthalene

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