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Widely used for protection of amino groups in peptide synthesis and multi-step organic synthesis of small molecules.
Xavier Ariza; Fèlix Urpí; Carles Viladomat; Jaume Vilarrasa. One-pot conversion of azides to Boc-protected amines with trimethylphosphine and Boc-ON. Tetrahedron Letters., 1998, 39 (49), 9101-9102.
A. Paul Krapcho; Christopher S. Kuell. Mono-Protected Diamines. N-tert-Butoxycarbonyl-α,ω-Alkanediamines from α,ω-Alkanediamines. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 1990, 20(16), 2559-2564.
Reagent for the preparation of Boc-derivatives of amino acids, preferred on safety grounds to the unstable t-butyl azidoformate. In aqueous dioxane and in the presence of triethylamine as base, reaction is rapid at room temperature. The organic by-product, 2-hydroxyimino-2-phenylacetonitrile is easily removed by extraction into an organic phase: Tetrahedron Lett., 4393 (1975); Bull. Chem. Soc. Jpn., 50, 718 (1977). See Appendix 6.
Hazard Statements: H302-H312-H332-H315-H319-H335
Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.