16466-61-8

Basic information

• Product Name: DI-TERT-BUTYL HYDRAZODICARBOXYLATE
• Synonyms: TERT-BUTYL HYDRAZODIFORMATE;N,N'-DI-BOC-HYDRAZINE;LABOTEST-BB LT00453977;DI-TERT-BUTYL HYDRAZODICARBOXYLATE;DI-TERT-BUTYL HYDRAZODIFORMATE;N,N-Di-tert-butoxycarbonylhydrazine~Di-tert-butyl hydrazodiformate~Hydrazine-N,N-dicarboxylic acid di-tert-butyl ester;di-tert-butyl bicarbamate;n,n'-di-tert-butoxycarbonylhydrazine
• CAS NO: 16466-61-8
• Molecular Formula: C₁₀H₂₀N₂O₄
• Molecular Weight: 232.28
• EINECS: 240-512-3
• Mol File: 16466-61-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 123-126 °C (dec.)(lit.)
• Boiling Point: 281.7 °C at 760 mmHg
• Flash Point: 124.2 °C
• Appearance: White/Powder or Crystalline Powder
• Density: 1.196 g/cm³
• Vapor Pressure: 0.00161mmHg at 25°C
• Refractive Index: 1.453
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 8.73±0.43(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 1794023
• CAS DataBase Reference: DI-TERT-BUTYL HYDRAZODICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DI-TERT-BUTYL HYDRAZODICARBOXYLATE(16466-61-8)
• EPA Substance Registry System: DI-TERT-BUTYL HYDRAZODICARBOXYLATE(16466-61-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 16466-61-8(Hazardous Substances Data)

Usage

Description

Di-tert-butyl hydrazodicarboxylate is a white powder chemical compound that acts as a hydrazine substrate during the preparation of protected pyridylhydrazine derivatives. It is commonly used as a starting reagent in various chemical synthesis processes.

Uses

Used in Chemical Synthesis:
Di-tert-butyl hydrazodicarboxylate is used as a starting reagent in the four-step synthesis of aminobicyclopyrazolone hydrochloride. It plays a crucial role in the formation of the final product, which can be used for various applications in the pharmaceutical and chemical industries.
Used in Pd-Catalyzed Amination Reactions:
Di-tert-butyl hydrazodicarboxylate is also used as a reagent during Pd-catalyzed amination reactions of halo-pyridine substrates. This reaction is an important step in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Preparation of Protected Pyridylhydrazine Derivatives:
As a hydrazine substrate, Di-tert-butyl hydrazodicarboxylate is used in the preparation of protected pyridylhydrazine derivatives. These derivatives are valuable intermediates in the synthesis of various heterocyclic compounds and can be further modified to obtain desired products.

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2725, 1960 DOI: 10.1021/ja01496a018

InChI:InChI=1/C10H20N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3,(H,11,13)(H,12,14)

Upstream product

• 870-50-8 di-tert-butyl (E)-azodicarboxylate 
• 98-80-6 phenylboronic acid 
• 870-50-8 di-tert-butyl-diazodicarboxylate 
• 24608-52-4 tert-butyl chloroformate 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 870-46-2 t-butoxycarbonylhydrazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50624-94-7 oxalic acid tert-butyl ester ethyl ester 
• 29518-83-0 S-Methyl-monothiokohlensaeure-tert.-butylester 
• 35454-04-7 oxalamic Acid Tert-butyl Ester 
• 39982-09-7 potassium tert-butyl carbonate 
• 6044-68-4 3,3-dimethoxyprop-1-ene 
• 14618-58-7 t-Butylcarbonic diethylphosphoricanhydrid 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 

Downstream Products

• 900863-80-1 C₂₂H₂₅N₅O₆ 
• 205862-12-0 C₅₂H₇₂N₆O₈ 
• 396732-02-8 C₂₂H₃₀N₂O₄ 
• 350792-39-1 C₅₀H₆₈N₆O₆ 
• 350792-37-9 di(t-butyl) 2a,14b-di(4-heptylphenyl)-1,4-dioxo-1,2,2a,3,4,5,8,9,10,11,14,14b-dodecahydro-2,3,4a,9,10,14a-hexaazacyclopenta[8,1]azuleno[5,6-b]anthracene-9,10-dicarboxylate 
• 843651-78-5 N,N'-di(tert-butoxycarbonyl)-N'-[2-(4-fluorophenyl)allyl]hydrazine 
• 340256-13-5 tert-butyl 2-[(tert-butyl)oxycarbonyl]perhydropyridazine-1-carboxylate 
• 630087-82-0 C₁₉H₂₈N₂O₄ 
• 185456-43-3 N-benzyl-N’-[(tert-butoxy)carbonyl](tert-butoxy)carbohydrazide 
• 250665-96-4 [2S,1'S,2'S]-(+)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-2-(3,5-dibenzyloxy-4-methoxyphenyl)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 250665-95-3 [2S,1'S,2'S]-(+)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4,5-trimethoxyphenyl)acetamide 
• 250665-93-1 [2S,1'S,2'S]-(+)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 250665-92-0 [2S,1'S,2'S]-(+)-2-(3,4-dimethoxyphenyl)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 146605-64-3 1,2-bis-tert-butoxycarbonylpyrazolidine 

Relevant articles and documents

Synthesis of Diprotected Monosubstituted Hydrazine Derivatives from tert-Butyl Carbazates and Boronic Acids

(Equation presented) Diprotected monosubstituted hydrazine derivatives have been prepared via the reaction of tert-butyl carbazates with boronic acids catalyzed by cuprous chloride at room temperature.

A Modular Approach to Arylazo-1,2,3-triazole Photoswitches

Azoheteroarenes make up an emerging class of photoswitchable compounds with unique photophysical properties and advantages over traditional azobenzenes. Therefore, methods for synthesizing azoheteroarenes are highly desirable. Here, we utilize azide-alkyne click chemistry to access arylazo-1,2,3-triazoles, a previously unexplored class of azoheteroarenes that exhibit high thermal stabilities and near-quantitative bidirectional photoconversion. Controlling the catalyst or 1,3-dipole grants access to both regioisomeric arylazotriazoles and arylazoisoxazoles, highlighting the versatility of our approach.

Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

Synthesis of 1,2,3-Triazole and pyrazole analogues as bioisosteres of biphenyl-neolignans

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