ChemicalBook Product Catalog Chemical Reagents Organic reagents Azo, diazo compound Di-tert-butyl hydrazodicarboxylate

Di-tert-butyl hydrazodicarboxylate

Product NameDi-tert-butyl hydrazodicarboxylate
CAS16466-61-8
MFC10H20N2O4
MW232.28
EINECS240-512-3
MOL File16466-61-8.mol

Chemical Properties

Melting point	123-126 °C (dec.)(lit.)
Boiling point	294.6±9.0 °C(Predicted)
Density	1.064±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	8.73±0.43(Predicted)
form	Powder or Crystalline Powder
color	White
Water Solubility	Insoluble in water.
BRN	1794023
InChI	InChI=1S/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)
InChIKey	TYSZETYVESRFNT-UHFFFAOYSA-N
SMILES	N(C(OC(C)(C)C)=O)NC(OC(C)(C)C)=O

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	29280000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

White powder

Uses

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.

Uses

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.

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.

Synthesis

24424-99-5

16466-61-8

General procedure for the synthesis of di-tert-butyl azodicarboxylate from di-tert-butyl dicarbonate: Hydrazine monohydrate (5.85 g, 85%, 200 mmol) was added dropwise to a methanol solution containing 50 ml of di-tert-butyl dicarbonate (48 g, 220 mmol) over a period of 30 min under ice bath cooling conditions. After the dropwise addition, the reaction mixture was stirred at room temperature for 3 hours. Subsequently, the methanol solvent was removed by rotary evaporator and 250 ml of n-hexane was added to the residue and the resulting white solid was collected by filtration and washed with n-hexane. A final white solid product of 19.34 g was obtained in 84% yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 20, p. 2715 - 2717
[2] Chemical Communications, 2011, vol. 47, # 1, p. 373 - 375
[3] Patent: CN104387418, 2016, B. Location in patent: Paragraph 0088; 0089; 0090
[4] Journal of the American Chemical Society, 2012, vol. 134, # 45, p. 18581 - 18584
[5] Patent: WO2014/22454, 2014, A1. Location in patent: Paragraph 0160

Di-tert-butyl hydrazodicarboxylate

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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