tert-Butyl carbazate

Base Information

• Chemical Name: tert-Butyl carbazate
• CAS No.: 870-46-2
• Deprecated CAS: 2408684-07-9
• Molecular Formula: C5H12N2O2
• Molecular Weight: 132.162
• Hs Code.: 29280090
• European Community (EC) Number: 212-795-3
• NSC Number: 60250
• DSSTox Substance ID: DTXSID7061227
• Nikkaji Number: J150.814H
• Wikidata: Q55525261
• Mol file: 870-46-2.mol

Synonyms:tert-butyl carbazate

Chemical Property of tert-Butyl carbazate

Chemical Property:

• Appearance/Colour: White to pale yellow lumps
• Vapor Pressure: 0.024mmHg at 25°C
• Melting Point: 39-42 °C(lit.)
• Refractive Index: 1.4496 (estimate)
• Boiling Point: 303.6 °C at 760 mmHg
• PKA: 10.74±0.20(Predicted)
• Flash Point: 94.7 °C
• PSA: 64.35000
• Density: 1.039 g/cm³
• LogP: 1.47600
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in ethanol and methanol.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.089877630
• Heavy Atom Count: 9
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl carbazate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, F
• Hazard Codes: T-F,T,F
• Statements: 48-36/37/38-24/25-11
• Safety Statements: 45-36/37/39-16-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NN
• General Description: Tert-Butyl carbazate is a versatile reagent used in organic synthesis, particularly for the preparation of hydrazine derivatives. It serves as a key intermediate in reductive hydrazination reactions, as demonstrated in the synthesis of 3-substituted L-fuco-azafagomines, which act as selective inhibitors of α-L-fucosidases. Additionally, it is employed as a precursor in ring-closing metathesis (RCM) reactions to generate fluorinated cyclic hydrazines, highlighting its utility in constructing biologically relevant heterocycles. Its role in these synthetic pathways underscores its importance in medicinal chemistry and the development of potential therapeutic agents.

Technology Process of tert-Butyl carbazate

There total 16 articles about tert-Butyl carbazate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tert-butyl phenyl carbonate (6627-89-0) → t-butoxycarbonylhydrazine (870-46-2)

Guidance literature:

With hydrazine hydrate; Heating;

DOI:10.1016/0040-4039(91)80694-2

Reference yield: 99.0%

tert-butyl 2,2,2-trichloroethyl hydrazine-1,2-dicarboxylate → t-butoxycarbonylhydrazine (870-46-2)

Guidance literature:

With chloro-trimethyl-silane; mischmetal (50 percent Ce, 25 percent La, 16 percent Nd, 6 percentPr); In tetrahydrofuran; for 2h; Heating;

Reference yield: 97.0%

di-tert-butyl dicarbonate (24424-99-5) → t-butoxycarbonylhydrazine (870-46-2)

Guidance literature:

With hydrazine hydrate;

DOI:10.1016/j.ejmech.2012.04.020

upstream raw materials:

S-Methyl-monothiokohlensaeure-tert.-butylester

tert-butyl phenyl carbonate

tert-butyl 2,2,2-trichloroacetate

α-Nitroisobuttersaeure-tert-butylester

Downstream raw materials:

3-(3,4-Dimethoxybenzyliden)-carbazinsaeure-tert-butylester

3-Phenyl-carbimidoyl-tert.butylcarbazat

N'-(2-aminoacetyl)hydrazinecarboxylic acid tert-butyl ester

Cinnamaldehyde t-Butoxycarbohydrazone

Refernces

RCM-mediated synthesis of fluorinated cyclic hydrazines

10.1055/s-2008-1032043

The research article details the synthesis of fluorinated cyclic hydrazine derivatives, which are significant due to their presence in biologically active compounds. The study employs ring-closing metathesis (RCM) as the key reaction to cyclize fluorinated and trifluoromethylated olefins into the desired hydrazines. The precursors for the RCM were prepared through a series of alkylation steps starting from diethyl azodicarboxylate or tert-butyl carbazate. The synthesized compounds were characterized using infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS). Crystallographic data for one of the synthesized hydrazines was also deposited, confirming its structure. The research provides a novel pathway to synthesize a potentially useful class of fluorinated cyclic hydrazines with potential pharmaceutical relevance.

Synthesis of novel 3-amino(hydroxy)methyl- l - Fuco -azafagomines as leads for selective inhibitors of α- L -fucosidases

10.1055/s-0029-1219906

The study reports the synthesis of 3-substituted L-fuco-azafagomines from D-lyxose, representing the first example of aza-C-glycosides with a biimino moiety. These compounds are potential selective inhibitors of a-L-fucosidases, enzymes involved in the biosynthetic processing of fucose-containing glycoconjugates and associated with various physiological and pathological events. The key step in the synthesis involves reductive hydrazination of a 1-deoxy-ketohexose with tert-butyl carbazate. The synthesized compounds, 3a and 3b, were tested for their inhibitory activities against twelve glycosidases, with 3a showing selective and competitive inhibition of a-L-fucosidase from bovine kidney. The study highlights the potential of these compounds as leads for developing new therapeutic agents targeting a-L-fucosidases.