1-(3,5-difluorobenzenesulfonyl)bicyclo[1.1.0]butane

EN300-6495224

Product class

Building Blocks

CAS number

1862202-13-8

MW

230.23

Purity

95%

Stock Availability

US, UA

Lead time

1-5 days delivery time

Reagent for installation of bicyclobutane and further remote diversification

1-((3,5-Difluorophenyl)sulfonyl)bicyclo[1.1.0]butane is a versatile reagent used for installing bicyclobutane onto amines and thiols, enabling remote diversification of molecules1. The reagent is a white solid, stable under ambient conditions, and recommended for long-term storage in a freezer. It exhibits high chemoselectivity for thiols over other functional groups and is used for late-stage functionalization of pharmaceuticals. A key feature of this reagent is the ability to remove the sulfone to reveal the parent bicyclobutane or use it as a handle for further remote diversification. Reported diversification reactions include deuterium labeling, allylation, fluorination, and olefination via a Julia reaction2.

Synonyms: None

1. Lopchuk, J. M.; Baran, P. S. 1-((3,5-Difluorophenyl)Sulfonyl)Bicyclo[1.1.0]Butane. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd: Chichester, UK, 2017; pp 1–3. https://doi.org/10.1002/047084289X.rn02057 2. Gianatassio, R.; Lopchuk, J. M.; Wang, J.; Pan, C.-M.; Malins, L. R.; Prieto, L.; Brandt, T. A.; Collins, M. R.; Gallego, G. M.; Sach, N. W.; Spangler, J. E.; Zhu, H.; Zhu, J.; Baran, P. S. Strain-Release Amination. Science (1979) 2016, 351 (6270), 241–246. https://doi.org/10.1126/science.aad6252

Name:

1-(3,5-difluorobenzenesulfonyl)bicyclo[1.1.0]butane

SMILES:

O=S(=O)(C=1C=C(F)C=C(F)C1)C23CC3C2

CAS number:

1862202-13-8

Product class:

Building Blocks

ACD number:

MFCD30533755

CLogP:

1.066

Class:

MedChem Highlights

Formula:

C₁₀H₈F₂O₂S

Subclass:

-

MW:

230.23