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

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 16466-61-8 differently. You can refer to the following data:
1. Di-tert-butyl hydrazodicarboxylate, is used as starting reagent during the four-step synthesis of the aminobicyclopyrazolone hydrochloride. It was used as reagent during Pd-catalyzed amination reactions of halo-pyridine substrates.
2. Di-tert-butyl hydrazodiformate was used as starting reagent during the four-step synthesis of the aminobicyclopyrazolone hydrochloride. It was used as reagent during Pd-catalyzed amination reactions of halo-pyridine substrates.

Synthesis Reference(s)

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

General Description

Di-tert-butyl hydrazodiformate acts as hydrazine substrate during the preparation of protected pyridylhydrazine derivatives.

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

• 24608-52-4 tert-butyl chloroformate 
• 870-50-8 di-tert-butyl-diazodicarboxylate 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 1129-28-8 3-methoxycarbonylbenzyl bromide 
• 870-46-2 t-butoxycarbonylhydrazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 39982-09-7 potassium tert-butyl carbonate 
• 870-50-8 di-tert-butyl (E)-azodicarboxylate 
• 6044-68-4 3,3-dimethoxyprop-1-ene 
• 98-80-6 phenylboronic acid 
• 14618-58-7 t-Butylcarbonic diethylphosphoricanhydrid 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 2168-84-5 methyl dithioacetate 
• 57022-34-1 tert-butyl cyanoformate 

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.

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.

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

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