2-Methyl-2-Propanesulfinamide, CAS No.: 146374-27-8

Product Name: 2-Methyl-2-propanesulfinamide

Synonyms: T-Butylsulfinamide; Tert-Butylsulfinamide; Tert-Butylsulphinamide; TERT-BUTANESULFINAMIDE; (S)-Tert-Butanesulfinamide; Racemic Tert Butylsulfinamide; 2-Methylpropane-1-Sulfinamide; Racemic 2-Methyl-2-propanesulfinamide; 2-Methyl-2-Propanesulfinamide, Racemic; 2-METHYL-PROPANE-2-SULFINIC ACID AMIDE; 2-Methyl-Propane-2-Sulfinic Acid Amide

CAS No.: 146374-27-8

EINECS No.: 1312995-182-4

Molecular Formula: C4H11NOS

Molecular Weight: 121.2

Brief Introduction:

2-Methyl-2-propanesulfinamide, also known as 2-methylpropane-2-sulfinamide or (S)-Tert-Butanesulfinamide, is a compound with a molecular formula of C4H11NOS and a molecular weight of 121.2012. 2-Methyl-2-propanesulfinamide is a new type of pharmaceutical intermediate and a key chiral source for the synthesis of chiral amine drugs. It is not only widely used in the synthesis of chiral drugs, but also can be used as a chiral ligand to induce catalytic asymmetric synthesis reactions.

Features:

As a chiral auxiliary, tert-butylsulphinamide has the following advantages:

(1) It is easy to form imines with various aldehydes or ketones;

(2) Due to the activation of tert-butylsulfenyl group, the generated imine is more electrophilic and easier to react with nucleophilic reagents or be reduced by metal boron reagents, inducing high diastereoselectivity;

(3) In the addition product, tert-butylsulfenyl group is also a good protecting group that can tolerate strong bases, transition metals, etc. in the reaction;

(4) Under acidic conditions, tert-butylsulfenyl group is easy to remove, and the resulting hydrochloride can be purified with ether solvents with an almost quantitative yield.

Synthetic Route:

Tert-butyl mercaptan is used as the raw material, oxidized by a catalyst and hydrogen peroxide, and then asymmetric oxidation is carried out by hydrogen peroxide, a vanadium catalyst and a chiral ligand to obtain chiral tert-butyl thiosulfinate, and then optically pure tert-butylsulfinamide is obtained under deep cooling conditions using liquid ammonia, metallic lithium and ferric nitrate.

Applications:

1) Used to synthesize 4-sulfonyliminopiperidine;

2) Tert-Butylsulfinamide can react with benzyl Grignard reagent to form 4-benzyl-4-aminopiperidine, an important pharmaceutical building block;

3) Tert-Butylsulfinamide can also be used to insert methylene into derivatized sulfonyl imines to prepare N-Tosylaziridine.

Packaging:

1kg/Aluminum Foil Bag, 5kg/Carton, 10kg/Carton, 25kg/Fibre Drum or according to the specific requirements from customers.

Storage Conditions:

Store in a sealed unopened container at a temperature ≤ 30°C and a humidity ≤ 75% RH; protect from heat, light and oxygen.

Shelf Life:

12 months if stored under above mentioned conditions.