4-FLUORO-1-NAPHTHALDEHYDE Chemical Properties

Melting point:

79-81 °C

Boiling point:

307.9±15.0 °C(Predicted)

Density 

1.249±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Off-White to Pale Beige

InChIKey

LZUCGZVKZDBILP-UHFFFAOYSA-N

Safety Information

Risk Statements 

52/53

Safety Statements 

61

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

4-FLUORO-1-NAPHTHALDEHYDE Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

4-Fluoro-1-naphthaldehyde (cas# 172033-73-7) is a compound useful in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 6592, 1995 DOI: 10.1021/jo00125a055

Synthesis

The general procedure for the synthesis of 4-fluoro-1-naphthalenecarboxaldehyde from 1,1-dichlorodimethyl ether and 1-fluoronaphthalene was as follows: a solution of 1,1-dichlorodimethyl ether (5.9 mL, 65 mmol) in methylene chloride (30 mL) was cooled in an ice bath, followed by the addition of stannum tetrachloride (7.6 mL, 65 mmol) drop-wise over a period of 15 min. After stirring for 45 minutes, a dichloromethane (30 mL) solution of 1-fluoronaphthalene (5.5 mL, 50 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was poured into ice water (100 mL) and diluted with dichloromethane (50 mL). The organic layer was separated and further diluted with dichloromethane (100 mL) followed by washing with water (3 x 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuum to give 4-fluoro-1-naphthaldehyde (7.62 g, 87% yield) as a pale yellow solid. Mass spectrum (ESI) m/z 175 (M + H)+.

References

[1] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6592 - 6594
[2] Patent: WO2004/52890, 2004, A1. Location in patent: Page 78
[3] Patent: CN105566284, 2016, A. Location in patent: Paragraph 0267; 0268
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3481 - 3486
[5] Patent: WO2008/407, 2008, A1. Location in patent: Page/Page column 57

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