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5331-43-1 - Benzyl carbazate, 98+% - Benzyl hydrazinocarboxylate - Benzyloxycarbonylhydrazine - A13005 - Alfa Aesar

A13005 Benzyl carbazate, 98+%

CAS Number
5331-43-1
Synonyms
Benzyl hydrazinocarboxylate
Benzyloxycarbonylhydrazine

Size Price ($) Quantity Availability
5g 33.30
25g 134.10
100g 456.29
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Benzyl carbazate, 98+%

MDL
MFCD00041890
EINECS
226-230-3

Chemical Properties

Formula
C8H10N2O2
Formula Weight
166.18
Melting point
66-70°
Solubility
Soluble in water (slightly), methanol and DMSO.

Applications

Benzyl carbazate is used as a reagent for preparation of benzyloxycarbonyl (Z, Cbz) hydrazides of carboxylic acids, particularly N-protected amino acids. Subsequent hydrogenolysis gives the hydrazide which can be converted to the azide for coupling with a further amino acid residue by the azide method. It is also used in the preparation of simple acyl or sulfonyl hydrazides avoiding diacylation.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Handle under inert gas. Protect from moisture. Incompatible with strong oxidizing agents.

Literature References

ABRAHAM N. KURTZ.; CARL NIEMANN. Synthesis and Properties of Ethyl 1-Acetyl-2-benzyl Carbazate, an Analog of Acetyl-D- and L-Phenylalanine Ethyl Ester1. J. Org. Chem. 1961, 26 (6), 1843-1846.

Louis A. Carpino. Oxidative Reactions of Hydrazines. II. Isophthalimides. New Protective Groups on Nitrogen1,2. J. Am. Chem. Soc. 1957, 79 (1), 98-101.

Reagent for preparation of benzyloxycarbonyl (Z, Cbz) hydrazides of carboxylic acids, particularly N-protected amino acids. Subsequent hydrogenolysis gives the hydrazide which can be converted to the azide for coupling with a further amino acid residue by the azide method: J. Am. Chem. Soc., 74, 470 (1952); 87, 620 (1965); see Appendix 6:

Has also been used in a similar manner for the preparation of simple acyl or sulfonyl hydrazides avoiding diacylation; the residual benzyl group is removable by hydrogenolysis: Synthesis, 244 (1980).

GHS Hazard and Precautionary Statements

Hazard Statements: H318-H315-H335

Causes serious eye damage. Causes skin irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P310-P362-P312-P405-P403+P233-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. Immediately call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1952982
Harmonized Tariff Code
2928.00
TSCA
Yes
RTECS
MV1724950

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