(S)-(-)-2-Methyl-2-propanesulfinamide, CAS No. 343338-28-3

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343338-28-3

Catalog No. EBD33160

CAS 343338-28-3

Name (S)-(-)-2-Methyl-2-propanesulfinamide

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Basic Information

Synonyms: (S)-(-)-Tert-ButylSulphinamide (S)-(-)-T-Butylmethylsulfinamide (S)-(-)-T-Butylsulfinamide 2-Methyl-2-Propane-Sulfinamide(S-Isomer) (S)-(+)-Tert-butanesulfinamide (S)-(-)-Tert-ButylSulphin (S)-tert-Butanesulfinamide (S)-(-)-2-Methyl-2-propanesulfinamide (S)-tert-butylsulfinamide S-(-)-T-Butylsulfinimide (S)-(-)-2-Methyl-2-Propanesulphinamide (S)-2-Methylpropane-2-Sulfinamide (S)-(-)-2-Methyl-Propane-2-SulfinicAcidAmide (S)-(-)-Tert-Butylsulfinamide

Molecular Formula: C4H11NOS

Molecular Weight: 121.2

MDL Number: MFCD05861480

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Chiral Auxiliaries and Resolution Reagents Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

(S)-(-)-2-Methyl-2-propanesulfinamide, also known as (S)-tert-butanesulfinamide, is a chiral sulfinamide compound with the CAS number 343338-28-3. It features a tert-butyl group attached to a sulfinamide moiety, with the sulfur atom bearing a stereogenic center in the S-configuration. This compound is a white to off-white crystalline solid, soluble in common organic solvents like dichloromethane and methanol. As a versatile chiral auxiliary, (S)-tert-butanesulfinamide is widely employed in asymmetric synthesis, particularly for the preparation of chiral amines via the sulfinimine (N-sulfinyl imine) methodology. It acts as a directing group in nucleophilic additions, enabling high diastereoselectivity in the formation of ж┴-branched amines, amino acids, and heterocyclic compounds. Its tert-butyl group provides steric bulk, enhancing stereochemical control, while the sulfinyl group can be easily removed under mild acidic conditions after the desired transformation. This reagent is a staple in medicinal chemistry and pharmaceutical research for constructing enantiomerically pure building blocks. It is also utilized in the synthesis of natural products and chiral ligands. Due to its stability and broad substrate scope, it is considered a fundamental tool in modern organic synthesis, often stored under inert atmosphere to prevent oxidation.

Physical Properties

Melting Point: 97-101 °C(lit.)

Boiling Point: 220 °C at 760 mmHg

Flash Point: 86.8 °C

Density: 1.124 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: white to light yellow crystal powder