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

A13860 Ethyl carbazate, 97%

CAS Number
4114-31-2
Synonyms
Ethoxycarbonylhydrazine
Ethyl hydrazinocarboxylate

Size Price ($) Quantity Availability
50g 40.41
250g 124.80
1000g 390.40
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Ethyl carbazate, 97%

MDL
MFCD00007595
EINECS
223-903-3

Chemical Properties

Formula
C3H8N2O2
Formula Weight
104.11
Melting point
44-47°
Boiling Point
85-86°/7mm
Flash Point
86°(186°F)
Sensitivity
Moisture Sensitive
Solubility
Very soluble in water.

Applications

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.

Notes

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

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H315-H319-H335

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

Precautionary Statements: P280h-P305+P351+P338-P309-P310

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: Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
878265
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2928.00
TSCA
Yes
RTECS
FE2545000

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