1-Fluoro-4-(1-methylethenyl)benzene Chemical Properties

Boiling point:

183°C

Density 

1.01 g/mL at 20 °C(lit.)

refractive index 

1.5085-1.5125

Flash point:

53 °C

storage temp. 

Sealed in dry,2-8°C

solubility 

soluble in Methanol

form 

clear liquid

color 

colorless to yellow/brown

BRN 

2039696

CAS DataBase Reference

350-40-3(CAS DataBase Reference)

NIST Chemistry Reference

4-FC6H4C(CH3)=CH2(350-40-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10

Safety Statements 

16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

3

PackingGroup 

III

HS Code 

2942000090

MSDS

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1-Fluoro-4-(1-methylethenyl)benzene Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid

Uses

4-Fluoro-a-methylstyrene is used in the synthesis of Paroxetine (P205750), which is a selective serotonin reuptake inhibitor. Used as an antidepressant.

Synthesis

GENERAL METHOD: Potassium tert-butoxide (t-BuOK, 2.47 g, 22.00 mmol) was added to an anhydrous tetrahydrofuran (THF, 70 mL) solution of methyltriphenylphosphonium bromide (7.12 g, 20.00 mmol) in four batches at 0 °C. The reaction mixture was stirred at 0 °C for 2 h, followed by slow dropwise addition of anhydrous THF (20 mL) solution of 4-fluoroacetophenone (20 mmol) over 30 min. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl, 50 mL) solution. The reaction solution was extracted three times with petroleum ether (3 x 50 mL). All organic phases were combined, washed with saturated saline (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Finally, the residue was purified by fast column chromatography using petroleum ether (Pet) as eluent to afford the target product 1-fluoro-4-(prop-1-en-2-yl)benzene.

References

[1] Tetrahedron, 2008, vol. 64, # 37, p. 8610 - 8617
[2] Organic Letters, 2018, vol. 20, # 18, p. 5747 - 5751
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 32, p. 8450 - 8453
[4] Angew. Chem., 2013, vol. 125, # 32, p. 8608 - 8611,4
[5] Tetrahedron, 2017, vol. 73, # 49, p. 6901 - 6905

1-Fluoro-4-(1-methylethenyl)benzene(350-40-3)Related Product Information

• 4-Vinylbenzyl chloride
• 2-METHYLSTYRENE
• Vinylbenzyl chloride
• 2-Aminobenzotrifluoride
• Allylbenzene
• 2-(Trifluoromethyl)benzoic acid
• (Trifluoromethoxy)benzene
• Trifluoromethanesulfonic acid
• 2-Phenyl-1-propene
• 4-Methylstyrene
• Xylene
• Trifluoropropene
• 3-(Trifluoromethyl)benzaldehyde
• Perfluoroethylene propylene copolymer
• POLY(ALPHA-METHYLSTYRENE)
• Benzene
• Fluorine
• 4-(4-FLUOROPHENYL)-1,2,3,6-TETRAHYDROPYRIDINE HYDROCHLORIDE