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Methyl carbazate

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CAS:6294-89-9
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  • 2026-05-28
  • CAS:6294-89-9
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Methyl carbazate Basic information
Product Name:Methyl carbazate
Synonyms:Carbomethoxyhydrazide;hydrazinecarboxylicacid,methylester;Methoxy carbonyl hydrazide;METHYL CARBAZATE;METHYL HYDRAZINOFORMATE;CARBAZIC ACID METHYL ESTER;Methyl carbazate, tech., 95%;Hydrazinocarboxylicacidmethylester
CAS:6294-89-9
MF:C2H6N2O2
MW:90.08
EINECS:228-560-3
Product Categories:Amines;Isotope Labelled Compounds;bc0001;6294-89-9
Mol File:6294-89-9.mol
Methyl carbazate Structure
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
pka10.52±0.20(Predicted)
form Crystalline Powder, Crystals or Platelets
color White to pink
Water Solubility soluble
BRN 1679395
InChI1S/C2H6N2O2/c1-6-2(5)4-3/h3H2,1H3,(H,4,5)
InChIKeyWFJRIDQGVSJLLH-UHFFFAOYSA-N
SMILESCOC(=O)NN
CAS DataBase Reference6294-89-9(CAS DataBase Reference)
NIST Chemistry ReferenceHydrazinecarboxylic acid, methyl ester(6294-89-9)
EPA Substance Registry SystemHydrazinecarboxylic 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 Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
Methoxycarbonylhydrazine English
ACROS English
SigmaAldrich English
ALFA English
Methyl carbazate Usage And Synthesis
Chemical PropertiesWHITE TO PINK CRYSTALLINE PLATELETS
UsesHydrazine derivative.
UsesMethyl 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
Dimethyl carbonate

616-38-6

Methyl carbazate

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 MethodsTo 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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