Safety and Handling:

• GHS Classification: Harmful if swallowed (H302), causes skin irritation (H315), and causes serious eye irritation (H319).
• Reactivity: Incompatible with strong bases and oxidizing agents.

Applications:

This compound is commonly used in chemical research for synthesizing nitrogen-containing compounds, including amino acids, and as a protected form of hydroxylamine in organic synthesis

N-Boc-Hydroxylamine (CAS 36016-38-3) is a protected amine derivative commonly used in organic synthesis, notably as a building block for pharmaceuticals. Its primary synonyms include tert-butyl N-hydroxycarbamate, N-(tert-butoxycarbonyl) hydroxylamine, and N-hydroxycarbamic acid tert-butyl ester.

Key Synonyms and Identifiers

• Common Name: N-Boc-Hydroxylamine, N-Boc-hydroxyamine, BocNHOH
• IUPAC Name: tert-Butyl N-hydroxycarbamate
• Chemical Name: N-(tert-Butoxycarbonyl)hydroxylamine
• Other Names: N-Hydroxycarbamic acid tert-butyl ester, 1,1-Dimethylethyl N-hydroxycarbamate, tert-Butyl hydroxycarbamate, N-tert-butoxycarbonyl hydroxylamine
• CAS Number: 36016-38-3
• MDL Number: MFCD00002107
• PubChem CID: 97534

Commonly Used Abbreviations

• BocNHOH
• HONHBoc
• N-Boc-hydroxylamine
• t-butyl-N-hydroxycarbamate

N-Boc-Hydroxylamine (CAS 36016-38-3), or tert-butyl N-hydroxycarbamate, is a versatile building block used primarily in organic synthesis for pharmaceutical development and chemical research. It serves as a protected reagent for introducing nitrogen, creating complex molecules, preparing aziridines, and generating functionalized polymers or prodrugs.

Key Applications and Uses:

• Pharmaceutical and Organic Synthesis:It is widely used to prepare amino acids and amino-containing molecules. It is particularly valuable as a protected hydroxylamine for constructing complex nitrogen-containing molecules, often used to develop novel therapeutic compounds.
• AziridinePreparation: Used in the synthesis of aziridines via the cycloaddition of azides with nitroso Diels-Alder adducts.
• Building Block for Derivatives:It functions as a reagent for synthesizing t-butyl-N-(acyloxy)carbamates and N,O-diacylated N-hydroxyarylsulfonamides.
• Functionalized Polymers and Materials:Applied in polymer chemistry for creating functionalized polymers for coatings and drug delivery systems.
• Analytical Chemistry:Employed for the derivatization of carbonyl compounds to improve their detection and quantification.
• Bioconjugation:It is utilized to facilitate the conjugation of biomolecules such as proteins and peptides, which is useful for creating diagnostics.

This reagent is highly valued by researchers for its stability and ease of handling compared to free hydroxylamine.