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Methyl carbazate

Product NameMethyl carbazate
CAS6294-89-9
MFC2H6N2O2
MW90.08
EINECS228-560-3
MOL File6294-89-9.mol

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
form	Crystalline Powder, Crystals or Platelets
pka	10.52±0.20(Predicted)
color	White to pink
Water Solubility	soluble
BRN	1679395
InChI	1S/C2H6N2O2/c1-6-2(5)4-3/h3H2,1H3,(H,4,5)
InChIKey	WFJRIDQGVSJLLH-UHFFFAOYSA-N
SMILES	COC(=O)NN
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	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29280000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
Methoxycarbonylhydrazine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

WHITE TO PINK CRYSTALLINE PLATELETS

Uses

Hydrazine derivative.

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.

Synthesis

616-38-6

6294-89-9

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

Methyl carbazate

Chemical Properties

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MSDS

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