1-Naphthoylchlorid

Bezeichnung:1-Naphthoylchlorid

CAS-Nr879-18-5

Englisch Name:1-Naphthoyl chloride

CBNumberCB8735331

SummenformelC11H7ClO

Molgewicht190.63

MOL-Datei879-18-5.mol

Synonyma

1-Naphthoylchlorid

1-Naphthoylchlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	16-19 °C (lit.)
Siedepunkt	190 °C/35 mmHg (lit.)
Dichte	1.265 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.652(lit.)
Flammpunkt	>230 °F
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	Chloroform (Slightly)
Aggregatzustand	Powder, Flakes or Crystals
Wichte	1.265
Farbe	White to almost white
Wasserlöslichkeit	Reacts with water.
Sensitive	Moisture Sensitive
BRN	775785
Stabilität	Stable. Incompatible with water, moisture, strong oxidizing agents, bases.
InChI	1S/C11H7ClO/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
InChIKey	NSNPSJGHTQIXDO-UHFFFAOYSA-N
SMILES	ClC(=O)c1cccc2ccccc12
CAS Datenbank	879-18-5(CAS DataBase Reference)
NIST chemische Informationen	1-Naphthalenecarbonyl chloride(879-18-5)
EPA chemische Informationen	1-Naphthalenecarbonyl chloride (879-18-5)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	34-37-14
S-Sätze:	26-36/37/39-45-28A-60-30-20-8
RIDADR	UN 3261 8/PG 2
WGK Germany	3
F	21
Hazard Note	Corrosive
TSCA	TSCA listed
HazardClass	8
PackingGroup	II
HS Code	29163990
Speicherklasse	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B

Gefahreninformationscode (GHS)

1-Naphthoyl chloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
R37:Reizt die Atmungsorgane.
R14:Reagiert heftig mit Wasser.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S30:Niemals Wasser hinzugießen.
S20:Bei der Arbeit nicht essen und trinken.
S8:Behälter trocken halten.
Chemische Eigenschaften
Low melting solid/Liquid
Verwenden
1-Naphthoyl chloride has been used:
- as derivatization reagent in analysis of short-chained dodecyl alcohol ethoxylates and dodecyl alcohol by solid-phase extraction combined with dispersive liquid-liquid microextraction method
- as fluorescent labeling reagent in determination of T-2 and HT-2 toxins by HPLC with fluorescence detection
- in Arndt-Eistert synthesis in the presence of trimethylsilyldiazomethane
- in preparation of 2-ethyl-1-pentyl-3-(1-naphthoyl)indole
Verwenden
1-Naphthoyl chloride has been used as derivatization reagent in analysis of short-chained dodecyl alcohol ethoxylates and dodecyl alcohol by solid-phase extraction combined with dispersive liquid-liquid micro extraction method, as fluorescent labeling reagent in determination of T-2 and HT-2 toxins by HPLC with fluorescence detection, in Arndt-Eistert synthesis in the presence of trimethylsilyldiazomethane and in preparation of 2-ethyl-1-pentyl-3-(1-naphthoyl)indole.
Synthese

86-55-5

879-18-5

General method: Method A: 1-Naphthalenecarboxylic acid (5.8 mmol) was dissolved in dry toluene (40 mL) and thionyl chloride (8.0 mmol) was added. After refluxing the reaction for 2 hours, evaporate under reduced pressure to remove the solvent and excess thionyl chloride to give 1-naphthalenecarboxylic acid as a colorless liquid in quantitative yield. Upon cooling, the product formed colorless needle-like crystals with a melting point of 18-19°C (literature value 26°C [54]). 1-Naphthalenecarbonyl chloride (5.8 mmol), triethylamine (8.7 mmol) and the corresponding substituted aniline (5.8 mmol) were dissolved in anhydrous dichloromethane (30 mL), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure, the solid residue was washed with 10% hydrochloric acid solution, the crude product was recrystallized with isopropanol and decolorized by the addition of activated carbon.
Einzelnachweise
[1] Molecules, 2014, vol. 19, # 7, p. 10386 - 10409
[2] Patent: WO2009/91324, 2009, A1. Location in patent: Page/Page column 29
[3] Organic Letters, 2005, vol. 7, # 3, p. 367 - 369
[4] Chemische Berichte, 1905, vol. 38, p. 180
[5] Chemische Berichte, 1868, vol. 1, p. 42

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