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A12383 tert-Butyl carbazate, 98+%

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

Stock No. Size Price ($) Quantity Availability
A12383-14 25g 58.40
A12383-22 100g 129.00
A12383-36 500g 491.00
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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)
Storage & Sensitivity
Keep Cold. 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-H301-H311-H315-H319-H335

Flammable solid. Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P240-P241-P261-P264b-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P361-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Remove/Take off immediately all contaminated clothing. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

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

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