1-Naphthoyl chloride

1-Naphthoyl chloride Property

Melting point:

16-19 °C (lit.)

Boiling point:

190 °C/35 mmHg (lit.)

Density 

1.265 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.652(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly)

form 

Powder, Flakes or Crystals

Specific Gravity

1.265

color 

White to almost white

Water Solubility 

Reacts with water.

Sensitive 

Moisture Sensitive

BRN 

775785

Stability:

Stable. Incompatible with water, moisture, strong oxidizing agents, bases.

CAS DataBase Reference

879-18-5(CAS DataBase Reference)

NIST Chemistry Reference

1-Naphthalenecarbonyl chloride(879-18-5)

EPA Substance Registry System

1-Naphthalenecarbonyl chloride (879-18-5)

Safety

Hazard Codes 

C

Risk Statements 

34-37-14

Safety Statements 

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 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

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

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P363Wash contaminated clothing before reuse.

P405Store locked up.

1-Naphthoyl chloride Chemical Properties,Usage,Production

Chemical Properties

Low melting solid/Liquid

Uses

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.

Uses

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

Synthesis

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.

References

[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