Benzyl carbazate, 98+%

Name: Benzyl carbazate, 98+%
SKU: A13005.14
Price: 165.00 EUR

CAS: 5331-43-1 | C8H10N2O2 | 166.18 g/mol

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Catalog number A13005.14

also known as A13005-14

Price (EUR)

165,00

Each

Quantity:

25 g

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Price (EUR)

165,00

Each

Chemical Identifiers

CAS5331-43-1

IUPAC Name(benzyloxy)carbohydrazide

Molecular FormulaC8H10N2O2

InChI KeyRXUBZLMIGSAPEJ-UHFFFAOYSA-N

SMILESNNC(=O)OCC1=CC=CC=C1

Specifications

Specification Sheet

Assay (GC)>98.0%

Appearance (Color)White to pale yellow

FormCrystalline powder or flakes

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Soluble in water (slightly), methanol and DMSO.

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.

RUO – Research Use Only

General 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).