4114-31-2

Basic information

• Product Name: Ethyl carbazate
• Synonyms: (Ethoxycarbonyl)hydrazide;(Monocarbethoxy)hydrazine;1-(Carbethoxy)hydrazine;1-(Ethoxycarbonyl)hydrazine;1-carbethoxyhydrazine;Carbethoxyhydrazine;ethoxycarbonylhydrazide;Ethyl carbazinate
• CAS NO: 4114-31-2
• Molecular Formula: C₃H₈N₂O₂
• Molecular Weight: 104.11
• EINECS: 223-903-3
• Product Categories: Pharmaceutical Intermediates;Miscellaneous;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 4114-31-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 44-47 °C(lit.)
• Boiling Point: 108-110 °C22 mm Hg(lit.)
• Flash Point: 187 °F
• Appearance: White to cream/Powder
• Density: 1.2719 (rough estimate)
• Vapor Pressure: 0.0399mmHg at 25°C
• Refractive Index: 1.4715 (estimate)
• Storage Temp.: 2-8°C
• PKA: 10.72±0.20(Predicted)
• Water Solubility: Very soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 878265
• CAS DataBase Reference: Ethyl carbazate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl carbazate(4114-31-2)
• EPA Substance Registry System: Ethyl carbazate(4114-31-2)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45
• RIDADR: 2811
• WGK Germany: 3
• RTECS: FE2545000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4114-31-2(Hazardous Substances Data)

Usage

Description

Ethyl carbazate, also known as N-hydroxyurethane, is an organic compound that serves as a synthetic intermediate in the production of various chemical compounds. It is characterized by its off-white crystalline appearance and is widely utilized in the chemical industry for the synthesis of different products.

Uses

1. Used in Pharmaceutical Industry:
Ethyl carbazate is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its ability to react with different reagents makes it a versatile building block in the synthesis of drugs.
2. Used in Chemical Synthesis:
Ethyl carbazate is used as a synthetic intermediate for the preparation of 4-phenylurazole, which can be further oxidized to yield 4-phenyl-1,2,4-triazole-3,5-dione. Ethyl carbazate is essential in the development of various chemical products.
3. Used in Analytical Chemistry:
Ethyl carbazate is used as a synthetic intermediate in the modification of procedures to isolate analytically pure monoalkylhydrazine hydrochlorides in greater than 90% yield, starting from a ketone or aldehyde.
4. Used in Organic Chemistry:
Ethyl carbazate is used in the treatment of primary amines with chloroamine or hydroxylamine-O-sulfonic acid, as well as in the condensation of a carbonyl compound with ethyl carbazate to form various organic compounds.
5. Used in Catalyst Synthesis:
Ethyl carbazate is used in the FeCl3-catalyzed reaction to produce β-hydroxyester in better yield, showcasing its utility in enhancing the efficiency of chemical reactions.
6. Used in Synthesis of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones:
Ethyl carbazate is used in a one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones through cyclocondensation with aryl nitriles, catalyzed by DMAP as an efficient and basic nucleophilic catalyst. This application highlights its role in the synthesis of complex organic compounds.

Hazard

Irritant.

Purification Methods

Fractionate 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].

InChI:InChI=1/C3H8N2O2/c1-2-5(4)3(6)7/h2,4H2,1H3,(H,6,7)/p-1

Upstream product

• 22012-90-4 nitrosourethane 
• 626-37-9 N-nitrourethane 
• 3206-31-3 tris(ethoxycarbonyl)amine 
• 541-41-3 chloroformic acid ethyl ester 
• 64-19-7 acetic acid 
• 105-58-8 Diethyl carbonate 
• 36133-63-8 N'-dichloromethylene-hydrazine-N,N-dicarboxylic acid diethyl ester 
• 58277-23-9 7-ethoxycarbonylamino-8-methyl-[1,3]dioxolo[4,5-g]quinazolinium betaine 
• 58277-22-8 4bH,13bH-bis[1,3]dioxolo[4,5-g;4',5'-g'][1,2,4,5]tetrazino[1,6-c;4,3-c']diquinazoline-5,14-dicarboxylic acid diethyl ester 
• 109-73-9 N-butylamine 
• 7803-57-8 hydrazine hydrate 
• 7647-01-0 hydrogenchloride 
• 101350-66-7 fluoren-9-ylidene-carbazic acid ethyl ester 
• 10203-17-5 fluoren-9-ylidene-hydrazine-N,N-dicarboxylic acid diethyl ester 

Downstream Products

• 116056-07-6 2,5,6,7-tetrahydro-pyrrolo[2,1-c][1,2,4]triazol-3-one 
• 118801-67-5 5,6,7,8-tetrahydro-1,2,4-triazolo<4,3-a>pyridin-3(2H)-one 
• 27182-43-0 3-oxo-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine 
• 5407-77-2 (5-nitro-furan-2-ylmethylene)-hydrazinecarboxylic acid ethyl ester 
• 4114-28-7 diethyl hydrazodicarboxylate 
• 98951-35-0 3-cyclohexyl-carbazic acid ethyl ester 
• 35558-93-1 (2-chloro-benzylidene)-carbazic acid ethyl ester 
• 103988-10-9 3-p-tolylthiocarbamoyl-carbazic acid ethyl ester 
• 114841-79-1 3-benzylthiocarbamoyl-carbazic acid ethyl ester 
• 35559-12-7 (3-nitro-benzylidene)-carbazic acid ethyl ester 
• 94822-37-4 (α'-hydroxy-bibenzyl-α-ylidene)-carbazic acid ethyl ester 
• 16208-36-9 ethyl 3-benzylidenecarbazate 
• 78266-66-7 (4-hydroxy-benzylidene)-carbazic acid ethyl ester 
• 17696-94-5 ethyl 2-(tert-butylcarbamoyl)hydrazine-1-carboxylate 

Relevant articles and documents

On triazoles. XXXIV. The correct structure of the ethoxycarboxylated 5-amino-1H-1,2,4-triazole and its product with hydrazine

The structure of the ethoxycarboxylated product of 5-amino-1H-1,2,4-triazole and its hydrazide was corrected using their ir, pmr, cmr and mass spectra.

Design and synthesis of novel cylopentapyrazoles bearing 1,2,3-thiadiazole moiety as potent antifungal agents

In drug-resistant phytopathogenic fungi, there has been extensive research on microbiological and antifungal drug development. In this study, a novel series of cylopentapyrazole bearing a 1,2,3-thiadiazole ring 2a-e were designed and synthesized according to the principle of combination of bioactive structures. Thus, we have employed a [3 + 2] cycloaddition with 4-methyl-[1,2,3] thiadiazole-5-carboxylic acid hydrazones 1a-e and cyclopentadiene ring. Novel synthesized compounds were identified with IR, 1H and 13C NMR, mass spectrometry and elemental analysis then, antifungal activities were assayed. Based on our study, a combination of the compounds 1a and 2b possess remarkable antifungal activity against Botrytis cinerea AHU 9424 with 100% inhibition. EC50 values were calculated by studying different doses in combinations with high inhibition rates. The combination of 1a + 2b has an EC50 value at 6.37 and 13.85 μg/ml concentrations against B. cinerea and F. culmorum, respectively. The combination of compound 1a + 2b, having a cylopentapyrazole ring on the 1,2,3-thiadiazole backbone, shows promising fungicidal activity and deserves further development. Additionally, the homology model of the CYP51 enzyme that belongs to Fusarium moniliforme was generated using CYP51B (PDB ID: 6CR2), and molecular docking was performed using this homology model for each compound. The results of this study clearly indicate that these novel compounds can be identified as promising lead compounds and potential fungicidal agents in future.

1. 2, 3 - thiadiazole - 5 - a amidine compound synthesis method

The invention discloses a novel method for synthesizing a 1,2,3-thiadiazole-5-formamidine compound. The target compound shown in general formula TDCA is prepared from a compound as shown in general formula M by virtue of a methylation reaction. The target component as shown in the general formula M is prepared from a compound as shown in general formula A and a compound as shown in general formula N by virtue of a condensation reaction, wherein during the methylation reaction, preferably, a catalyst is an organic metallic catalyst consisting of cuprous iodide and a ligand, namely 2,2,6,6-tetramethyl-3,5-heptadione; during the reaction, preferably, dimethylbenzene is taken as a solvent, and the optimum reaction temperature is 100-140 DEG C. The method disclosed by the invention is high in yield and more environment-friendly (as shown in Specification).