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ALD00558

Sigma-Aldrich

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

95%

Synonym(s):

Baran cyclobutylation reagent

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About This Item

Empirical Formula (Hill Notation):
C10H8F2O2S
Molecular Weight:
230.23
UNSPSC Code:
12352101
PubChem Substance ID:
329772718
NACRES:
NA.22

Assay

95%

form

powder or crystals

reaction suitability

reaction type: C-C Bond Formation

storage temp.

2-8°C

General description

1-((3,5-Difluorophenyl)sulfonyl)bicyclo[1.1.0]butane can be used as a cyclobutylation agent to introduce bicyclobutane group onto a variety of amines and thiols without affecting other functional groups.

Application

The following "spring-loaded" electrophile is a convenient reagent for the installation of cyclobutane to primary and secondary amines. This product is one of several synthetically useful reagents reported by Baran and coworkers on strain-release amination.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

593230

Phenyllithium solution

1-((3, 5-Difluorophenyl) sulfonyl) bicyclo [1.1. 0] butane
Lopchuk JM and Baran PS
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-3 (2001)

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Baran Group – Professor Product Portal

The Baran Group works with Sigma-Aldrich in providing a portfolio of zinc-based reagents promoting difluoromethylation, trifluoromethylation, trifluoroethylation and isopropylation of aryl and heteroaryl motifs. Baran’s lab has also helped introduce a portable desaturase (Tz0Cl), which promotes the installation of alcohol and amine groups and leaves behind a highly useful tosyl group for further transformations.

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