(R)-(+)-2-Methyl-2-propanesulfinamide
[CAS# 196929-78-9]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Sulfonamides and synergists
• Name: (R)-(+)-2-Methyl-2-propanesulfinamide
• Synonyms: (R)-2-methylpropane-2-sulfinamide
• Molecular Formula: C₃H₁₁CNOS
• Molecular Weight: 121.20
• CAS Registry Number: 196929-78-9
• EC Number: 676-338-3
• SMILES: CC(C)(C)[S@@](=O)N

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 103-107 °C (Expl.)
• alpha: 4 ° (c=1, CHCl3 + amylenes)
• alpha: 4 (Expl.)
• Index of Refraction: 1.523, Calc.^*
• Boiling Point: 220.0±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 86.8±22.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(R)-(+)-2-Methyl-2-propanesulfinamide, commonly known as (R)-tert-butanesulfinamide, is an organosulfur compound that has become a valuable reagent in asymmetric synthesis. First introduced in the 1990s by Professor Jonathan Ellman, this chiral auxiliary compound has since gained widespread use in organic chemistry, particularly in the synthesis of chiral amines. Ellman’s work highlighted the compound’s potential as a robust, enantioselective tool for introducing chiral centers in synthetic molecules, paving the way for its use in pharmaceuticals and other fine chemicals.

The principal application of (R)-(+)-2-methyl-2-propanesulfinamide is in the asymmetric synthesis of amines, which are critical intermediates in the production of many pharmaceuticals. Due to the reagent’s high stereoselectivity, (R)-tert-butanesulfinamide facilitates the synthesis of chiral amines with excellent enantiomeric purity. The process involves forming imines with carbonyl compounds and subsequently reducing them to yield chiral amines. This reaction pathway is highly efficient and allows chemists to control the stereochemistry of the product. This capability is particularly important in drug synthesis, as the stereochemistry of chiral centers can significantly influence the biological activity and safety profile of pharmaceuticals. As a result, (R)-(+)-2-methyl-2-propanesulfinamide has become an essential reagent in the development of drugs with high enantiomeric purity.

Beyond amine synthesis, (R)-(+)-2-methyl-2-propanesulfinamide is also useful in asymmetric transformations in complex molecule synthesis. In the creation of bioactive molecules, such as alkaloids and natural product derivatives, the reagent’s chiral sulfinyl group enables precise stereochemical control, which is often crucial for biological function. This utility extends to agrochemicals and materials science, where the synthesis of enantiomerically pure compounds can optimize activity and performance.

The compound’s stability, ease of handling, and versatility have also contributed to its popularity in research and industry. Unlike other chiral auxiliaries, (R)-tert-butanesulfinamide is both commercially available and stable under typical storage conditions, making it accessible and reliable for synthetic chemists. Its application extends to laboratories and industrial settings where enantiomeric purity and stereocontrol are essential.

References

2022. Synthesis of (+)-Cochlearol B. *Synfacts*.
DOI: 10.1055/s-0041-1738541

2021. Synthesis of Chiral o-Aminobenzylamines by Stereoselective Addition of Grignard Reagents to N-[(o-Aminophenyl)methylene] sulfinamides. *Synlett*.
DOI: 10.1055/a-1423-5679

2017. An efficient synthesis of structurally diverse 2-methyl-N-[(3-phenylamino)oxetan-3-yl]-2-propanesulfinamide derivatives under catalyst free conditions. *Chemical Papers*.
DOI: 10.1007/s11696-017-0237-1