4-(Bromomethyl)benzenesulfonyl fluoride

• CAS: 7612-88-6
• Catalog Number: ACM7612886
• Category: Alkanes
• Molecular Weight: 253.09
• Hazard Statements: H304
• RIDADR: UN 3261 8 / PGII
• Symbol: GHS08

Case Study

4-(Bromomethyl)Benzenesulfonyl Fluoride Used for the Synthesis of Benzyl Quinolone Carboxylic Acid Analogues

Davie, Briana J., et al. Journal of medicinal chemistry, 2014, 57(12), 5405-5418.

Benzylquinolone carboxylic acid (BQCA) functions as both a positive allosteric modulator and an agonist for the M1 muscarinic acetylcholine receptor. This research described both the creation of 4-(bromomethyl)benzenesulfonyl fluoride (p-sulfonylfluorobenzyl bromide, 5) and its use as an irreversible allosteric ligand for the M1 mAChR GPCR. The N-benzylation reaction between the compound 5 and 4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3) produces fluorosulfonyl analog 4c (1-(4-(fluorosulfonyl)benzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid).
The resulting 4c retains BQCA's pharmacological activity, effectively binding (pK_B) and activating (τ_B) the M1 mAChR. Furthermore, 4c demonstrates positive binding (α) and functional (β) synergy with the endogenous neurotransmitter acetylcholine (ACh) in CHO cells stably expressing the receptor, mirroring the cooperative effects observed with BQCA.

4-(Bromomethyl)Benzenesulfonyl Fluoride for the Synthesis of Functional RAFT Agents via One-Pot Route

Wang, Peixi, et al. Macromolecular Rapid Communications, 2018, 39(3), 1700523.

The research introduced a new method for cyclic polymer ring-closing by combining reversible addition-fragmentation chain transfer polymerization (RAFT) with hexavalent sulfur-fluorine exchange (SuFEx) click reaction. The novel functional RAFT agent TBDMS-FSBCT was produced through a one-pot synthesis procedure using TBDMS-Thio, carbon disulfide, and 4-(bromomethyl)benzenesulfonyl fluoride.
Synthesis of the RAFT agent TBDMS-FSBCT
Combined TBDMS-Thio (1.24 g, 6.45 mmol), carbon disulfide (1.48 g, 19.35 mmol), potassium phosphate (1.46 g, 6.45 mmol) and 4-(bromomethyl)benzenesulfonyl fluoride (1.63 g, 6.45 mmol) in 10 mL of acetone to create a solution. After stirring the mixture overnight at room temperature it was acidified to pH < 2 using concentrated hydrochloric acid before being extracted three times using dichloromethane. Anhydrous magnesium sulfate was used to dry the organic phase. The dichloromethane solvent evaporated to leave a crude product which underwent purification by silica gel column chromatography using ethyl acetate and hexane in a 1:1 volume ratio. The reaction produced a light yellow solid which weighed 2.36 grams and represented a 78% yield.

Custom Q&A

What is the molecular formula of 4-(Bromomethyl)benzenesulfonyl fluoride?

The molecular formula of 4-(Bromomethyl)benzenesulfonyl fluoride is C7H6BrFO2S.

What is the molecular weight of 4-(Bromomethyl)benzenesulfonyl fluoride?

The molecular weight of 4-(Bromomethyl)benzenesulfonyl fluoride is 253.09 g/mol.

What is the IUPAC name of 4-(Bromomethyl)benzenesulfonyl fluoride?

The IUPAC name of 4-(Bromomethyl)benzenesulfonyl fluoride is 4-(bromomethyl)benzenesulfonyl fluoride.

What is the InChI of 4-(Bromomethyl)benzenesulfonyl fluoride?

The InChI of 4-(Bromomethyl)benzenesulfonyl fluoride is InChI=1S/C7H6BrFO2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5H2.

What is the InChIKey of 4-(Bromomethyl)benzenesulfonyl fluoride?

The InChIKey of 4-(Bromomethyl)benzenesulfonyl fluoride is WWAPDVQUZYCNCR-UHFFFAOYSA-N.

What is the Canonical SMILES of 4-(Bromomethyl)benzenesulfonyl fluoride?

The Canonical SMILES of 4-(Bromomethyl)benzenesulfonyl fluoride is C1=CC(=CC=C1CBr)S(=O)(=O)F.

What is the CAS number of 4-(Bromomethyl)benzenesulfonyl fluoride?

The CAS number of 4-(Bromomethyl)benzenesulfonyl fluoride is 7612-88-6.

What is the European Community (EC) Number of 4-(Bromomethyl)benzenesulfonyl fluoride?

The European Community (EC) Number of 4-(Bromomethyl)benzenesulfonyl fluoride is 809-755-8.

What is the XLogP3 value of 4-(Bromomethyl)benzenesulfonyl fluoride?

The XLogP3 value of 4-(Bromomethyl)benzenesulfonyl fluoride is 2.9.

Is 4-(Bromomethyl)benzenesulfonyl fluoride a canonicalized compound?

Yes, 4-(Bromomethyl)benzenesulfonyl fluoride is a canonicalized compound.