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560871

Sigma-Aldrich

2-Methyl-2-propanesulfinamide

97%, racemic

Synonym(s):

(±)-tert-Butylsulfinamide, 1,1-Dimethylethylsulfinamide, 2-Methyl-2-propanesulfinamide, 2-Methylpropan-2-sulfinamide, tert-Butanesulfinamide, tert-Butylsulfinamide

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About This Item

Linear Formula:
(CH3)3CS(O)NH2
CAS Number:
146374-27-8
Molecular Weight:
121.20
MDL number:
MFCD01863616
UNSPSC Code:
12352100
PubChem Substance ID:
24879898
NACRES:
NA.22

Assay

97%

form

solid

mp

97-101 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)S(N)=O

InChI

1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3

InChI key

CESUXLKAADQNTB-UHFFFAOYSA-N

Application

Ellman′s Sulfinamides
Synthesis of 4-sulfonyliminopiperidine and its reaction with benzyl Grignard to form an important pharmaceutical building block, 4-benzyl-4-aminopiperidne. Also used to prepare spiro tosylaziridines via methylene insertion into the derived sulfonylimine.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Synlett, 2565-2565 (2006)
Synlett, 833-833 (2006)

Articles

Ellman's Sulfinamides

Ellman's sulfinamide is available in both enantiomeric and racemic forms for your research. This versatile and useful auxiliary has found extensive use both in academics and industry.

Related Content

Ellman Group – Professor Product Portal

The Ellman group has participated in the development of a variety of C-H functionalization methods. An electron rich phosphine ligand has proven to be very useful for a variety of Rh(I)-catalyzed C-C bond forming reactions applicable to heterocycle synthesis as exemplified in the recent Science paper “Proton Donor Acidity Controls Selectivity in Nonaromatic Nitrogen Heterocycle Synthesis.” Another useful ligand developed for the highly functional group compatible direct arylation of nitrogen heterocycles is described in a 2008 J. Am. Chem. Soc. paper “Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight.” The Ellman group also developed the chiral amine reagent tert-Butanesulfinamide, which is extensively used in academics and industry for the asymmetric synthesis of amines. A comprehensive survey of tert-Butanesulfinamide methods and applications up through 2009 is provided in the 2010 Chemical Reviews article, “Synthesis and Applications of tert-Butanesulfinamide.”

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