4-Fluorobenzenesulfonyl chloride Chemical Properties

Melting point:

29-31 °C (lit.)

Boiling point:

95-96 °C/2 mmHg (lit.)

Density 

1.467 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

dioxane: 0.1 g/mL, clear

form 

Crystalline Low Melting Mass

color 

White to light brown

Sensitive 

Moisture Sensitive

BRN 

2091633

Stability:

Moisture Sensitive

InChI

InChI=1S/C6H4ClFO2S/c7-11(9,10)6-3-1-5(8)2-4-6/h1-4H

InChIKey

BFXHJFKKRGVUMU-UHFFFAOYSA-N

SMILES

C1(S(Cl)(=O)=O)=CC=C(F)C=C1

CAS DataBase Reference

349-88-2(CAS DataBase Reference)

EPA Substance Registry System

Benzenesulfonyl chloride, 4-fluoro- (349-88-2)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-28-36/37/39-45-28A-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

Hazard Note 

Corrosive

TSCA 

T

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

MSDS

• Language:English Provider:4-Fluorobenzenesulfonyl chloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Fluorobenzenesulfonyl chloride Usage And Synthesis

Chemical Properties

white to light brown crystalline low melting mass

Uses

4-Fluorobenzenesulfonyl Chloride is found to be an excellent activating agent for the covalent attachment of biological substances to a variety of solid supports e.g. Sepharose beads. 4-Fluorobenzenesulfonyl Chloride is also used as a reagent for the studies of proteins by fluorine NMR.

Synthesis

The general procedure for the synthesis of 4-fluorobenzenesulfonyl chloride from p-fluorobenzenethiol is as follows: a mixture of mercaptan (1 mmol), 30% H2O2 (3 mmol, 0.3 mL), and TiCl4 (1 mmol, 0.11 mL) was reacted in CH3CN with stirring at 25 °C for the time referred to in Table 1.The reaction was carried out by the immediate precipitation of white solid (TiO2) . The progress of the reaction was monitored by TLC, and upon completion of the reaction, the reaction mixture was quenched by the addition of H2O (10 mL) and subsequently extracted with EtOAc (4 × 5 mL). The organic phases were combined and dried with anhydrous MgSO4. The filtrate was concentrated under reduced pressure to give an analytically pure product. The product can be further purified by short silica gel column chromatography and structurally confirmed by 1H NMR, 13C NMR spectroscopic analysis and comparison of melting points with real samples prepared by known methods.

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 24, p. 9287 - 9291
[2] Synlett, 2009, # 17, p. 2773 - 2776
[3] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 10, p. 3692 - 3695
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2012, vol. 187, # 6, p. 769 - 775
[5] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5847 - 5850

4-Fluorobenzenesulfonyl chloride(349-88-2)Related Product Information

• Benzyl chloride
• alpha-Toluenesulfonyl chloride
• Benzenesulfonyl chloride
• 4-Fluorophenol
• Ammonium chloride
• Calcium chloride
• Sodium chloride
• Mepiquat chloride
• Choline chloride
• Polyvinyl chloride
• N-Acetylsulfanilyl chloride
• 4-Nitrobenzenesulfonyl chloride
• 4-fluoro-3-methylbenzenesulfonyl chloride
• 2,3,4-TRIFLUOROBENZENESULFONYL CHLORIDE
• 2-CHLORO-4-FLUOROBENZENESULFONYL CHLORIDE
• 2,4,5-Trifluorobenzenesulfonyl chloride
• 2-Nitrobenzenesulfonyl chloride
• 3-Nitrobenzenesulfonyl chloride