DI-TERT-BUTYL HYDRAZODICARBOXYLATE 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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DI-TERT-BUTYL HYDRAZODICARBOXYLATE Usage And Synthesis

Chemical Properties

White powder

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.

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.

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

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

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