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:

99.9% ^*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
• Uses: Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates via photoorganocatalytic hydroacylation of dialkyl azodicarboxylates with aldehydes in presence of phenylglyoxylic acid as photocatalyst. Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions. Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.

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:

Thieno<3,2-c>pyridazin

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

C₂₆H₃₁N₃O₆

1,2-bis(t-butyloxycarbonyl)hydrazine

Refernces

• 1、 Du, Wanting,Ma, Zichao,Shao, Liming,Wang, Jian. "Hydrogen peroxide based oxidation of hydrazines using HBr catalyst". . . Retrieved 2021/11/18.
• 2、 Sakurai, Masayoshi,Kihara, Nobuhiro,Watanabe, Nobuhiro,Ikari, Yoshihiro,Takata, Toshikazu. "Synthesis of α-aminocarbonyl compounds via hetero dielsalder reaction". supporting information. p. 144 - 147. Retrieved 2018/01/01.