1094627-41-4

Usage

Uses

Used in Pharmaceutical and Chemical Research:
2-Amino-2-(2-methylphenyl)ethan-1-ol is used as a building block for the synthesis of various drugs and molecules. Its unique structure, containing both an amino group and a hydroxyl group, allows for the creation of a wide range of compounds with diverse therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Amino-2-(2-methylphenyl)ethan-1-ol serves as a valuable intermediate for the production of various organic compounds. Its ability to participate in a range of chemical reactions makes it a useful component in the synthesis of complex organic molecules.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
2-Amino-2-(2-methylphenyl)ethan-1-ol is also utilized as a chiral auxiliary in asymmetric synthesis. This application is crucial for the production of enantiomerically pure compounds, which are essential in many pharmaceutical and chemical applications where the stereochemistry of a molecule can significantly impact its biological activity and efficacy.

Upstream product

• 19819-98-8 2-o-tolylethanol 
• 2783-26-8 o-methylstyrene oxide 

Relevant academic research and scientific papers

Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines

The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.