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497401

Sigma-Aldrich

(R)-(+)-2-Methyl-2-propanesulfinamide

98%

Sinónimos:

(R)-2-methyl-2-propanesulfinamide, (R)-2-methylpropane-2-sulfinamide, (R)-tert-butanesulfinamide, (R)-tert-butylsulfinamide

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1 G
$69.82
5 G
$177.00
25 G
$311.00

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1 G
$69.82
5 G
$177.00
25 G
$311.00

About This Item

Fórmula lineal:
(CH3)3CS(O)NH2
Número de CAS:
196929-78-9
Peso molecular:
121.20
Número MDL:
MFCD05861479
Código UNSPSC:
12352111
ID de la sustancia en PubChem:
24873117
NACRES:
NA.22

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Ensayo

98%

actividad óptica

[α]20/D +4°, c = 1.0242 in chloroform stab. with amylenes

mp

103-107 °C (lit.)

temp. de almacenamiento

2-8°C

cadena SMILES

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

InChI

1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1

Clave InChI

CESUXLKAADQNTB-SSDOTTSWSA-N

Categorías relacionadas

Descripción general

(R)-(+)-2-Methyl-2-propanesulfinamide is a chiral auxiliary used in the condensation of the aldehyde. [1]

Aplicación

Ellman′s Sulfinamides
(R)-(+)-2-Methyl-2-propanesulfinamide may be used to prepare N-(1-cyclohexylmethylidene)-2-methylpropane-2-sulfinamide via copper mediated condensation with cyclohexane carboxaldehyde.[2] It may also be used to prepare (20E)-N-[t-butyl-(R)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the development of androgen receptor antagonists.[3]
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.[4]
Preparation of ß-chloro sulfinamides in a synthesis of chiral azridines.[5] Also used to prepare an organocatalyst for enantioselective reduction of imines.[6]
Useful reagent for synthesizing chiral amines.[7][8][9]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKCW1907
MKCT9317
MKCT2204
MKCR4737
MKCN8525

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Bram Denolf et al.
Organic letters, 8(14), 3129-3132 (2006-06-30)
[reaction: see text] Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with
Asymmetric synthesis of a, a-difluoro-?-amino acid derivatives from enantiomerically pure N-tert-butylsulfinimines.
Staas, DD, et al.
The Journal of Organic Chemistry, 67(23), 8276-8279 (2002)
A stereoselective synthesis of (S)-2-(((3-fluoro-4-methylphenoxy) carbonyl)(1-(4-((5-methyl-2-phenyloxazol-4-yl) methoxy) phenyl) ethyl) amino) acetic acid, a highly potent PPAR alpha gamma dual agonist
Xinhua Q et al.
Tetrahedron, 71, 9408-9414 (2015)
Dong Pei et al.
Organic letters, 8(25), 5913-5915 (2006-12-01)
Easily accessible chiral sulfinamide 2 has been developed as the first highly efficient and enantioselective organocatalyst relying solely on a chiral sulfur center for stereochemical induction. In the presence of 20 mol % of 2, a broad range of N-aryl
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
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Artículos

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.

Contenido relacionado

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. 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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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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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