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513210

Sigma-Aldrich

(S)-(−)-2-Methyl-2-propanesulfinamide

97%

Synonym(s):

(S)-(-)-tert-Butanesulfinamide, (S)-(-)-tert-Butyl sulfinamide, (S)-2-Methyl-2-propanesulfinamide, (S)-tert-Butanesulfinamide, (S)-tert-Butylsulfinamide

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About This Item

Linear Formula:
(CH3)3CS(O)NH2
CAS Number:
343338-28-3
Molecular Weight:
121.20
MDL number:
MFCD05861480
UNSPSC Code:
12352111
PubChem Substance ID:
24873681
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

97%

optical activity

[α]20/D −4.5°, c = 1 in chloroform

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/t7-/m0/s1

InChI key

CESUXLKAADQNTB-ZETCQYMHSA-N

Application

Ellman′s Sulfinamides
(S)-(-)-2-Methyl-2-propanesulfinamide may be used to develop benzofuran-based farnesyltransferase inhibitors as anti-cancer agents.[1] It may also be used to prepare (20E)-N-[t-butyl-(S)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the preparation of androgen receptor antagonists.[2]
Can be readily transformed into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones, which can undergo iridium-catalyzed asymmetric hydrogenation of olefins.[3]
Chiral auxiliary used in an asymmetric preparation of trifluoroethylamines by conversion of trifluoroacetaldehyde to a chiral imine followed by treatment with an aryl lithium and acidic methanolysis.[4]
Useful reagent for synthesizing chiral amines.[5][6][7]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ1917
MKCK8329
MKCC8950
MKCB1775V
MKBZ2676V

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Vouy Linh Truong et al.
Organic letters, 9(4), 683-685 (2007-01-30)
Condensation of N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give highly diastereomerically enriched adducts 5a-g. Acidic methanolysis of 5a-g provided the desired 1-aryl-2,2,2-trifluoroethylamine hydrochloride compounds
Synthesis and structure-activity relationships of novel benzofuran farnesyltransferase inhibitors.
Asoh K, et al.
Bioorganic & Medicinal Chemistry Letters, 19(6), 1753-1757 (2009)
20-Aminosteroids as a novel class of selective and complete androgen receptor antagonists and inhibitors of prostate cancer cell growth.
Fousteris MA, et al.
Bioorganic & Medicinal Chemistry Letters, 18(19), 6960-6969 (2010)
Journal of the American Chemical Society, 119, 9913-9914 (1997)
Jeffrey P McMahon et al.
Organic letters, 6(10), 1645-1647 (2004-05-07)
Addition of alkyl or aryl Grignard reagents to N-sulfinyl imines derived from 3- and 4-substituted cyclohexanones proceeds with good yields and with excellent diasteroselectivity. The selectivity of the reaction is controlled by the ring substituent rather than the sulfinyl group
View All Related Papers

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.

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.

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.

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

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

Ellman Group – Professor Product Portal

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

Ellman Group – Professor Product Portal

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

Ellman Group – Professor Product Portal

Ellman group developed electron-rich phosphine ligands for C-H functionalization and tert-Butanesulfinamide for asymmetric amine synthesis.

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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