Bis(3,5-difluorophenyl)sulfoxide

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Cat Number

INT2055858278

CAS Number

2055858-27-8

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Product Detail Description Customer Q&A

CAS Number

2055858-27-8

Synonyms

1,1′-Sulfinylbis[3,5-difluorobenzene;Benzene, 1,1'-sulfinylbis[3,5-difluoro-;5,5'-Sulfinylbis(1,3-difluorobenzene)

Molecular Formula

C12H6F4OS

Molecular Weight

274.23

Smiles

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

Boiling Point

360.6℃

Relative Density

1.52

General Description

Bis(3,5-difluorophenyl)sulfoxide is a symmetrical sulfoxide bearing two 3,5-difluorophenyl groups attached to the sulfoxide (S=O) sulfur center. The dual difluorination at the meta positions of both phenyl rings provides a unique electronic and steric profile: the electron-withdrawing fluorine atoms lower the phenyl ring's electron density, modifying the sulfoxide's dipole moment and H-bonding capacity, while the meta substitution pattern avoids steric interference at the para positions critical for biological interactions.

Mechanism of Action

Bis(3,5-difluorophenyl)sulfoxide functions as a molecular scaffold in medicinal chemistry. The sulfoxide group is chiral (due to tetrahedral sulfur), allowing for the synthesis of enantiomerically pure derivatives. The 3,5-difluoro substitution pattern is a common feature in CNS drug candidates, as it reduces metabolic oxidation at the aromatic ring and improves lipophilicity. The sulfoxide can act as a hydrogen bond acceptor and can be further oxidized to the corresponding sulfone.

Application

Bis(3,5-difluorophenyl)sulfoxide is used as an intermediate in the synthesis of fluorinated pharmaceutical candidates targeting CNS disorders, including NMDA receptor modulators, serotonin receptor ligands, and enzyme inhibitors. The 3,5-difluorophenyl moiety is prevalent in modern CNS drug design due to its favorable ADME properties and reduced metabolic liability. The symmetrical structure simplifies synthetic routes and facilitates SAR studies.

What is the recommended storage condition for Bis(3,5-difluorophenyl)sulfoxide?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for Bis(3,5-difluorophenyl)sulfoxide?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

Is Bis(3,5-difluorophenyl)sulfoxide available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

What functional groups in Bis(3,5-difluorophenyl)sulfoxide are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

What quality standards govern the production of Bis(3,5-difluorophenyl)sulfoxide?

Production is carried out under GMP-aligned quality systems with full traceability and documented quality controls for each manufacturing run.