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

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

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

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 870-46-2 t-butoxycarbonylhydrazine 
• 57022-34-1 tert-butyl cyanoformate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2168-84-5 methyl dithioacetate 
• 870-50-8 di-tert-butyl (E)-azodicarboxylate 
• 870-50-8 di-tert-butyl-diazodicarboxylate 
• 6044-68-4 3,3-dimethoxyprop-1-ene 
• 50624-94-7 oxalic acid tert-butyl ester ethyl ester 
• 1129-28-8 3-methoxycarbonylbenzyl bromide 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 24608-52-4 tert-butyl chloroformate 
• 29518-83-0 S-Methyl-monothiokohlensaeure-tert.-butylester 
• 35454-04-7 oxalamic Acid Tert-butyl Ester 

Downstream Products

• 870-50-8 di-tert-butyl-diazodicarboxylate 
• 173723-91-6 6,7-Bis-bromomethyl-1,4-dihydro-phthalazine-2,3-dicarboxylic acid di-tert-butyl ester 
• 152940-67-5 6-(Toluene-4-sulfonyl)-4,6-dihydro-1H-pyrrolo[3,4-d]pyridazine-2,3-dicarboxylic acid di-tert-butyl ester 
• 187850-51-7 5-Phenyl-6-(toluene-4-sulfonyl)-4,6-dihydro-1H-pyrrolo[3,4-d]pyridazine-2,3-dicarboxylic acid di-tert-butyl ester 
• 201600-30-8 di(tert-butyl) 4-[2a,7b-di(4-heptyl-phenyl)-1,4-dioxo-perhydro-2,3,4a,7a-tetraaza-cyclopenta[cd]inden-6-yliden]-1,2-pyrazolidine-dicarboxylate 
• 342635-34-1 bis(1,1-dimethylethyl) 1-(5-bromo-2-pyridyl)hydrazine-1,2-dicarboxylate 
• 146605-64-3 1,2-bis-tert-butoxycarbonylpyrazolidine 
• 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 
• 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 
• 250665-95-3 [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 
• 250665-96-4 [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 
• 185456-43-3 N-benzyl-N’-[(tert-butoxy)carbonyl](tert-butoxy)carbohydrazide 
• 630087-82-0 C₁₉H₂₈N₂O₄ 
• 65578-58-7 di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate 

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.

Copper salt catalyzed addition of arylboronic acids to azodicarboxylates

The addition of arylboronic acids 1 to azodicarboxylates 2 in the presence of a catalytic amount of a copper salt under mild reaction conditions gives aryl-substituted hydrazines 3 in high yields. The reaction is tolerant of a wide variety of functional groups.

Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.

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.

Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.

A containing hydrazine nitrogen phosphorus ligand complex and its in ester the application of the catalytic hydrogenation of

The invention relates to a composition containing hydrazine nitrogen and phosphorus ligands and application of the composition in catalytic hydrogenation with ester. The invention relates to the metal composition which is shown by a general formula MXY (L) and a method for preparing alcohols through hydrogenation reduction of carbonyl compounds such as ketones and estersby using the composition as catalysts. In the MXY (L), the M is metal Fe, Ru, Os, Co, Rh, Ir and other transition group metal, the X and the Y can be the same anion ligand or different anion ligands, and the L is a tetradentate ligand containing -NH-pyridyl and two heteroatoms. The composition disclosed by the invention has the advantages that the catalytic activity is high and the stability is strong.

Visible light-mediated decarboxylative amination of indoline-2-carboxylic acids catalyzed by Rose Bengal

A visible light-induced decarboxylative amination of indoline-2-carboxylic acids and azodicarboxylate esters has been developed, in which the oxidation of α-amino acids provides a versatile CO2-extrusion platform to generate α-aminoalkyl radicals. The corresponding products were obtained with yields of up to 72% catalyzed by a metal-free photocatalyst under mild conditions.

ORGANOCATALYTIC CARBONYL-OLEFIN AND OLEFIN-OLEFIN METATHESIS

The present invention provides, inter alia, organocatalytic carbonyl-olefin metathesis process. This process involves contacting a carbonyl-containing moiety with an olefin-containing moiety in the presence of a catalyst and under conditions sufficient to form a metathesis product with the proviso that the process takes place in the absence of photochemical promotion, stoichiometric amounts of transition metals, and Brnsted and Lewis acid catalysts. The present invention also provides an organocatalytic olefin-olefin metathesis process. This process involves contacting a first olefin-containing moiety with a second olefin-containing moiety in the presence of a catalyst and under conditions sufficient to form a metathesis product with the proviso that the process takes place in the absence of stoichiometric amounts of transition metals. Products made by the processes disclosed herein are also provided.

Efficient synthesis of cyclopropylhydrazine salts

An efficient procedure for the synthesis of cyclopropylhydrazine in the form of its salts is reported. The copper salt-catalyzed addition of cyclopropylboronic acid to the azo group of di-tert-butyl azodicarboxylate and subsequent deprotection gave the cy