2-Fluoroethyl 4-methylbenzenesulfonate Chemical Properties

Boiling point:

140°C/1mmHg(lit.)

Density 

1.290 g/cm3

refractive index 

1.5060 to 1.5100

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Clear Colourless to Pale Brown

InChI

InChI=1S/C9H11FO3S/c1-8-2-4-9(5-3-8)14(11,12)13-7-6-10/h2-5H,6-7H2,1H3

InChIKey

XNRDLSNSMTUXBV-UHFFFAOYSA-N

SMILES

C(OS(C1=CC=C(C)C=C1)(=O)=O)CF

CAS DataBase Reference

383-50-6(CAS DataBase Reference)

Safety Information

HS Code 

2930909899

2-Fluoroethyl 4-methylbenzenesulfonate Usage And Synthesis

Uses

2-Fluoroethyl Tosylate is an intermediate used in the preparation and pre-clinical evaluation of new class of high-affinity 18F-labeled PSMA ligands for detection of prostate cancer by positron emission tomography (PET) imaging.

Synthesis

2-Fluoroethanol (1.00 mL, 16.9 mmol), p-toluenesulfonyl chloride (3.85 g, 20.2 mmol), N-methylmorpholine (9.30 mL, 84.5 mmol), and dichloromethane (50 mL) were added to the reaction vessel, and the reaction was stirred for 17 hours at room temperature. After completion of the reaction, water was added to the reaction system and extracted with ethyl acetate three times to combine the organic layers. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by fast silica gel column chromatography (eluent: ethyl acetate/hexane=19:81→40:60) to afford fluoroethyl p-toluenesulfonate (3.79 g, 17.2 mmol, yield >100%) as a pale yellow liquid.1H NMR (600 MHz, CDCl3): δ 7.81 (d, J=8.4 Hz, 2H), δ 7.36 (d, J=8.4 Hz, 2H), 4.63-4.60 (m, 1H), 4.55-4.52 (m, 1H), 4.31-4.27 (m, 1H), 4.26-4.23 (m, 1H), 2.46 (s, 3H). lRMS (EI) Calculated value (C9H11F3O): 218.0, measured value: 218.0.

References

[1] Patent: US2018/30074, 2018, A1. Location in patent: Paragraph 0188-0191
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2008, vol. 51, # 7, p. 286 - 292
[3] Patent: US2013/177501, 2013, A1. Location in patent: Paragraph 0168
[4] Patent: US9168317, 2015, B2. Location in patent: Page/Page column 25; 26
[5] Patent: US9314541, 2016, B2. Location in patent: Page/Page column 26

2-Fluoroethyl 4-methylbenzenesulfonate(383-50-6)Related Product Information

• Ethyl p-toluenesulfonate
• P-Toluenesulfonic anhydride
• p-Toluenesulfonic acid
• Iron(III) p-toluenesulfonate
• Tosufloxacin tosylate
• Sodium p-toluenesulfonate
• Propargyl p-toluenesulfonate
• Methyl 2-(4-methylphenylsulfonamido)acetate
• 3-Butynyl p-toluenesulfonate
• 2,2,2-TRIFLUOROETHYL P-TOLUENESULFONATE
• HEXAFLUOROISOPROPYL TOSYLATE
• 1H,1H-PENTAFLUOROPROPYL P-TOLUENESULFONATE
• 2,2,3,3,4,4,4-HEPTAFLUOROBUTYL P-TOLUENESULFONATE
• 1H,1H,5H-OCTAFLUOROPENTYL P-TOLUENESULFONATE
• 1H,1H-PERFLUOROHEPTYL P-TOLUENESULFONATE
• 1H,1H,7H-DODECAFLUOROHEPTYL P-TOLUENESULFONATE
• 4-(HEPTAFLUOROISOPROPOXY)HEXAFLUOROBUTANOIC ACID
• 1H,1H,9H-PERFLUORONONYL P-TOLUENESULFONATE