Ethyl carbazate

Ethyl carbazate Basic information
Product Name:Ethyl carbazate
Synonyms:(Ethoxycarbonyl)hydrazide;(Monocarbethoxy)hydrazine;1-(Carbethoxy)hydrazine;1-(Ethoxycarbonyl)hydrazine;AKOS 90785;Ethoxycarbonylhydrazine~Ethyl hydrazinocarboxylate;ETHOXY CARBONYLHYDRAZINE;ETHOXY FORMHYDRAZINE
CAS:4114-31-2
MF:C3H8N2O2
MW:104.11
EINECS:223-903-3
Product Categories:Pharmaceutical Intermediates;Miscellaneous;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines;bc0001
Mol File:4114-31-2.mol
Ethyl carbazate Structure
Ethyl carbazate Chemical Properties
Melting point 44-47 °C (lit.)
Boiling point 108-110 °C/22 mmHg (lit.)
density 1.2719 (rough estimate)
refractive index 1.4715 (estimate)
Fp 187 °F
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
form Powder
pka10.72±0.20(Predicted)
color White to cream
Water Solubility Very soluble in water.
Sensitive Moisture Sensitive
BRN 878265
InChIKeyVYSYZMNJHYOXGN-UHFFFAOYSA-N
CAS DataBase Reference4114-31-2(CAS DataBase Reference)
NIST Chemistry ReferenceHydrazinecarboxylic acid, ethyl ester(4114-31-2)
EPA Substance Registry SystemHydrazinecarboxylic acid, ethyl ester (4114-31-2)
Safety Information
Hazard Codes Xi,T
Risk Statements 36/37/38-25
Safety Statements 26-36-45
RIDADR 2811
WGK Germany 3
RTECS FE2545000
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29280090
MSDS Information
ProviderLanguage
Carboethoxy hydrazine English
SigmaAldrich English
ACROS English
ALFA English
Ethyl carbazate Usage And Synthesis
Chemical PropertiesOff-white crystals.
UsesPrepare 4-phenylurazole from ethyl carbazate and then oxidize the urazole with gaseous dinitrogen tetroxide to yield 4-phenyl-1,2,4-tri- azoline-3,5-dione la. Modification of the ethyl carbazate procedure in which analytically pure monoalkylhydrazine hydrochlorides were isolated in greater than 90% yield, starting from a ketone or aldehyde. Treatment of primary amines is with chloroamine or hydroxylamine-0-sulfonic acid and the condensation of a carbonyl compound with ethyl carbazate. The FeCl 3 -catalyzed reaction of ethyl carbazate (2 b) proceeded readily to give β-hydroxyester 3 b in better yield. A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is described.
UsesSynthetic intermediate.
HazardIrritant.
Purification MethodsFractionate the carbazate using a Vigreux column (p 11) until the distillate crystallises [Allen & Bell Org Synth Coll Vol III 404 1955, Beilstein 3 IV 174].
Methyl carbazate Carbobenzoxyhydrazide Tebufenozide Ethyl carbazate hydrazine hydrate 1,3,4-OXADIAZOL-2(3H)-ONE, 5-PHENYL- Ethyl pyruvate Adipic dihydrazide Carbohydrazide Poly-AminoEthylFormate METHOXYFENOZIDE ISOXADIFEN-ETHYL DIETHYL HYDRAZODICARBOXYLATE Ethoxy 3-AMINO-2-OXAZOLIDINONE Furazolidone N-NITROSO-N-METHYLURETHANE tert-Butyl carbazate

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