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

A12383 tert-Butyl carbazate, 98+%

CAS Number
870-46-2
Synonyms
Boc-hydrazine
tert-Butoxycarbonylhydrazine

Size Price ($) Quantity Availability
25g 56.65
100g 122.57
500g 416.70
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tert-Butyl carbazate, 98+%

MDL
MFCD00007593
EINECS
212-795-3

Chemical Properties

Formula
C5H12N2O2
Formula Weight
132.16
Melting point
37-41°
Boiling Point
63-65°/0.1mm
Flash Point
91°(195°F)
Sensitivity
Moisture Sensitive
Solubility
Soluble in ethanol and methanol.

Applications

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.

Notes

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

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H228

Flammable solid.

Precautionary Statements: P210-P280-P240-P241-P370+P378a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. In case of fire: Use for extinction: CO2, powder or water spray.

Other References

Beilstein
1756967
Hazard Class
4.1
Packing Group
III
Harmonized Tariff Code
2928.00
TSCA
Yes

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