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4114-31-2 - Ethyl carbazate, 97% - Ethoxycarbonylhydrazine - Ethyl hydrazinocarboxylate - A13860 - Alfa Aesar

A13860 Ethyl carbazate, 97%

Codice CAS
4114-31-2
Sinonimi
Ethoxycarbonylhydrazine
Ethyl hydrazinocarboxylate

Dimensioni Prezzo ($) Quantità Disponibilità
50g 42,60
250g 153,00
1000g 478,00
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Ethyl carbazate, 97%

MDL
MFCD00007595
EINECS
223-903-3

Proprietà chimiche

Formula
C3H8N2O2
Peso formula
104.11
Punto di fusione
44-47°
Punto di ebollizione
85-86°/7mm
Punto di infiammabilità
86°(186°F)
Sensibilità
Moisture Sensitive
Solubilità
Very soluble in water.

Applicazioni

Prepare 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.

Note

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.

Letteratura

A. Davoodnia,; M. Bakavoli,; M. Soleimany,;H. Behm. A new one-pot neat synthesis of 1,2,4-triazol-3-ones through 4-(N,N-dimethylamino) pyridine (DMAP) catalyzed cyclocondensation of ethyl carbazate with aryl nitriles. Chinese Chemical Letters. 2008, 19 (6),685-688.

N. I. Ghali,; D. L. Venton,; S. C. Hung,; G. C. Le Breton. High-yielding synthesis of monoalkylhydrazines. J. Org. Chem., . 1981, 46 (26), 5413-5414.

Forms crystalline ethoxycarbonyl hydrazones with aldehydes and ketones. With o-acylphenols, Pb(OAc)4 treatment of the resulting hydrazone results in replacement of the phenolic OH with ethoxycarbonyl, providing a route to ethyl o-acylbenzoates: Tetrahedron Lett ., 31, 6781 (1990).

Reaction with methyl ketones, followed by treatment with SOCl2, leads to 4-substituted 1,2,3-thiadiazoles: J. Am. Chem. Soc., 77, 5359 (1955). In the presence of base, these readily lose N2 to give alkynethiolates: Can. J. Chem., 46, 1057 (1968):

More recently, this sequence has been used in the synthesis of dendrimers from 1,3,5-triacetylbenzene: J. Chem. Soc., Perkin 1, 2203 (1994).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H300-H315-H319-H335

Fatal if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P280h-P305+P351+P338-P309-P310a

Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell:

Altri riferimenti

Beilstein
878265
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2928.00
TSCA
Yes
RTECS
FE2545000

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