Methyl carbazate Chemical Properties

Melting point:

70-73 °C (lit.)

Boiling point:

108 °C/12 mmHg (lit.)

Density 

1.3348 (rough estimate)

refractive index 

1.4368 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

578g/l

pka

10.52±0.20(Predicted)

form 

Crystalline Powder, Crystals or Platelets

color 

White to pink

Water Solubility 

soluble

BRN 

1679395

InChIKey

WFJRIDQGVSJLLH-UHFFFAOYSA-N

CAS DataBase Reference

6294-89-9(CAS DataBase Reference)

NIST Chemistry Reference

Hydrazinecarboxylic acid, methyl ester(6294-89-9)

EPA Substance Registry System

Hydrazinecarboxylic acid, methyl ester (6294-89-9)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-48-23/25-25

Safety Statements 

26-37/39-45-38-36/37/39-22-36/37

RIDADR 

2811

WGK Germany 

3

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29280000

MSDS

• Language:English Provider:Methoxycarbonylhydrazine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl carbazate Usage And Synthesis

Chemical Properties

WHITE TO PINK CRYSTALLINE PLATELETS

Uses

Methyl carbazate was used in the preparation of methyl 3-(4-methyl-benzyl-idene)carbazate. It was also used in the synthesis of imidazo[1,5-d][1,2,4]triazines. It is used as pharmaceutical intermediate.

Uses

Hydrazine derivative.

Synthesis

General procedure for the synthesis of methyl hydrazinecarboxylate from dimethyl carbonate: Dimethyl carbonate (1, 45.0 g, 0.50 mol) and hydrazine hydrate (29.4 mL, 0.48 mol) were added to a 250 mL round-bottomed flask and the unit was equipped with a condenser. The reaction mixture was heated to 50°C with continuous stirring for 30 minutes, followed by continued stirring at room temperature for 24 hours. After completion of the reaction, water, methanol and excess dimethyl carbonate were removed by distillation under reduced pressure. The product was dried to give white crystals of methyl hydrazinecarboxylate (2, 42.3 g) in 94% yield with a melting point of 69-70°C. The 1H NMR (300 MHz, CDCl3) data were as follows: δ 3.73 (s, 3H, CH3-O), 3.77 (d, 2H, J = 1.85 Hz, -NH2), 6.09 (s, 1H, -NH).

Purification Methods

To remove impurities, the material is melted and pumped under vacuum until the vapours are spectroscopically pure [Caminati et al. J Am Chem Soc 108 4364 1986]. Distil it in a vacuum. [Beilstein 3 I 46.]

References

[1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 10, p. 4279 - 4286
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8172 - 8175
[3] Angew. Chem., 2014, vol. 126, # 31, p. 8311 - 8314,4
[4] Chinese Chemical Letters, 2017, vol. 28, # 2, p. 372 - 376
[5] Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1238 - 1242

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