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870-46-2 - tert-Butyl carbazate, 98+% - Boc-hydrazine - tert-Butoxycarbonylhydrazine - A12383 - Alfa Aesar

A12383 tert-Butyl carbazate, 98+%

Codice CAS
870-46-2
Sinonimi
Boc-hydrazine
tert-Butoxycarbonylhydrazine

Dimensioni Prezzo ($) Quantità Disponibilità
25g 56,10
100g 121,00
500g 472,00
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tert-Butyl carbazate, 98+%

MDL
MFCD00007593
EINECS
212-795-3

Proprietà chimiche

Formula
C5H12N2O2
Peso formula
132.16
Punto di fusione
37-41°
Punto di ebollizione
63-65°/0.1mm
Punto di infiammabilità
91°(195°F)
Sensibilità
Moisture Sensitive
Solubilità
Soluble in ethanol and methanol.

Applicazioni

tert-Butyl carbazate is used in a palladium-catalyzed cross-coupling with vinyl halides to prepare N-Boc-N-alkenylhydrazines. It is utilized in solid phase peptide synthesis and in the optical purity determination of alfa-amino aldehyde. It reacts with aldehydes to get hydrazones, which finds application as an intermediate in the synthesis of HIV-1 protease inhibitors. In addition to this, it is used as a starting material for the preparation of BOC-azide, sulfonic and carboxylic hydrazides.

Note

Store in a cool place. Incompatible with strong oxidizing agents and strong bases.

Letteratura

Protected hydrazine derivative, permitting selective reaction at one N atom, followed by mild acidic cleavage of the Boc group. For preparation of, e.g. N-aminosuccinimide, free from the cyclic hydrazide, see: J. Org. Chem., 37, 2040 (1972). Similarly, reaction with carbonyl or sulfonyl halides, followed by cleavage with HCl, provides a route to monoacyl hydrazides: Synthesis, 244 (1980). It is also commonly used in the synthesis of aza-amino acids; see, for example: Synthesis, 141 (1991) and references therein.

Monoalkylhydrazines can be prepared via reduction of Boc-hydrazones with borane-THF, and cleavage with HCl: J. Org. Chem., 46, 5413 (1981).

Precursor of the somewhat unstable tert-butyl azidoformate, useful for introduction of the Boc protecting group, see: Org. Synth. Coll., 5, 157 (1973). Caution! Possible violent decomposition of this azide on heating.

Karpenko, I. A.; Margathe, J. F.; Rodriguez, T.; Pflimlin, E.; Dupuis, E.; Hibert, M.; Durroux, T.; Bonnet, D. Selective Nonpeptidic Fluorescent Ligands for Oxytocin Receptor: Design, Synthesis, and Application to Time-Resolved FRET Binding Assay. J. Med. Chem. 2015, 58 (5), 2547-2552.

Kheirabadi, M.; Shi, L.; Bagheri, R.; Kabiri, K.; Hilborn, J.; Ossipov, D. A. In situ forming interpenetrating hydrogels of hyaluronic acid hybridized with iron oxide nanoparticles. Biomater. Sci. 2015, 3 (11), 1466-1474.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H228

Flammable solid.

Dichiarazioni precauzionali: P260u-P201-P280a-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310a-P405-P501a

Obtain special instructions before use. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. 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.

Altri riferimenti

Beilstein
1756967
Classe di rischio
4.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2928.00
TSCA
Yes

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