Di-tert-butyl azodicarboxylate

Base Information

• Chemical Name: Di-tert-butyl azodicarboxylate
• CAS No.: 870-50-8
• Molecular Formula: C10H18N2O4
• Molecular Weight: 230.264
• Hs Code.: 29270000
• European Community (EC) Number: 212-796-9
• NSC Number: 109889
• Mol file: 870-50-8.mol

Synonyms:di-tert-butyl azodicarboxylate

Chemical Property of Di-tert-butyl azodicarboxylate

Chemical Property:

• Appearance/Colour: yellow crystals or crystalline powder
• Vapor Pressure: 0.00253mmHg at 25°C
• Melting Point: 89-92 °C
• Refractive Index: 1.459
• Boiling Point: 287.1 °C at 760 mmHg
• Flash Point: 107.2 °C
• PSA: 77.32000
• Density: 1.06 g/cm³
• LogP: 3.30880
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: Insoluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 230.12665706
• Heavy Atom Count: 16
• Complexity: 267

Purity/Quality:

98% HPLC ^*data from raw suppliers

Di-tert-butyl azodicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F
• Hazard Codes: Xi,F
• Statements: 36/37/38-11
• Safety Statements: 26-36-37/39-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C
• General Description: Di-tert-Butyl azodicarboxylate (DBAD) is a key reagent used in Mitsunobu reactions, where it acts as an oxidizing agent alongside triphenylphosphine to facilitate the conversion of alcohols into esters or other functional groups. It is also employed in copper-catalyzed tandem oxidation-olefination processes, demonstrating its versatility in organic synthesis for constructing complex molecules under mild, environmentally friendly conditions. Its role in these reactions highlights its importance in facilitating selective transformations, such as the synthesis of sulfoxides, sulfones, and alkenes, while maintaining compatibility with various functional groups.

Technology Process of Di-tert-butyl azodicarboxylate

There total 7 articles about Di-tert-butyl azodicarboxylate 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%

1,2-bis(t-butyloxycarbonyl)hydrazine (16466-61-8) → di-tert-butyl-diazodicarboxylate (870-50-8)

Guidance literature:

With pyridine; bromine; In dichloromethane; at 0 ℃; for 0.25h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → di-tert-butyl-diazodicarboxylate (870-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / methanol / Inert atmosphere

2: pyridine; bromine / dichloromethane / Inert atmosphere

With pyridine; bromine; hydrazine hydrate; In methanol; dichloromethane;

DOI:10.1021/ja309650u

Reference yield:

tert-butyl chloroformate (24608-52-4) → di-tert-butyl-diazodicarboxylate (870-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine / ethanol; water / 0.5 h / 10 - 20 °C

2: pyridine; bromine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

With pyridine; bromine; hydrazine; In ethanol; dichloromethane; water;

DOI:10.1039/c6ob02770a

upstream raw materials:

1,2-bis(t-butyloxycarbonyl)hydrazine

triphenylbismuth(V) diacetate

di-tert-butyl dicarbonate

tert-butyl chloroformate

Downstream raw materials:

di-tert-butyl 1-tosylhydrazine-1,2-dicarboxylate

C₂₂H₃₆N₃O₆P

C₁₇H₂₃F₃N₂O₄

(3(2S),4S)-3-(2-(N,N'-bis-(t-butoxycarbonyl)hydrazino)-3-methyl-1-oxobutyl)-4-(phenylmethyl)-2-oxazolidinone

Refernces

Synthesis of 8-arylsulfoxyl/sulfonyl adenines

10.1016/j.tetlet.2004.11.009

The research presents a novel method for synthesizing 9-N-alkyl-8-arylsulfoxyl adenines and 9-N-alkyl-8-arylsulfonyl adenines. The process begins with a one-pot tandem reaction using Mitsunobu conditions to convert 8-arylsulfanyl adenines into iminophosphorane-protected 9-N-alkyl-8-arylsulfanyl adenines. Key chemicals involved in this initial step include triphenylphosphine (PPh3) and di-tert-butylazodicarboxylate (DBAD). Subsequently, the compounds undergo selective oxidation mediated by OXONE? and alumina, resulting in sulfoxides and sulfones. The oxidation step is crucial and is influenced by the stoichiometry of OXONE?, with excess OXONE? favoring sulfone formation. The final step involves deprotection of the amine using acetic acid (AcOH) and ethanol (EtOH) under reflux conditions to obtain the desired products. The research highlights the importance of protecting the C6 amino group with an iminophosphorane group to withstand strong oxidizing conditions and the necessity of carefully controlling reaction conditions to achieve the desired oxidation state on sulfur. The study provides a convenient method for producing an array of 8-arylsulfoxyl/sulfonyl adenine derivatives, which have potential applications in biological research and drug development.

Copper-catalyzed tandem oxidation-olefination process

10.1021/ol802299d

The research presents a novel catalytic sequence for the aerobic oxidation-ole?nation process using a single, inexpensive copper catalyst. The purpose of this study is to develop a more environmentally friendly and efficient one-pot method for converting alcohols into alkenes, which is a significant transformation in organic synthesis. The key chemicals used include copper chloride (CuCl), 1,10-phenanthroline as a ligand, di-tert-butyl azodicarboxylate (DBAB), trimethylsilyldiazomethane (TMSCHN2), triphenylphosphine, and various alcohols as substrates. The reaction conditions involve aerobic oxidation followed by ole?nation, with the copper catalyst facilitating both steps. The study concludes that this method is highly functional group compatible, works under nonbasic conditions, and can be applied to a wide range of primary and secondary alcohols, yielding alkenes in good to excellent yields without racemization of chiral substrates. The process is also compatible with various diazocarbonyl reagents, allowing for the synthesis of different types of alkenes. This work highlights a significant advancement in green chemistry by minimizing solvent and reagent usage and avoiding the isolation of sensitive intermediates.

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