3-amino-4-pyrazolecarboxylic acid ethyl ester
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid; sodium nitrite In ethanol for 1h; Heating; | 99% |
With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 0.5h; | 80 g |
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 20℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid for 16h; Reflux; | 97% |
With thionyl chloride at 0 - 20℃; for 3h; | 80% |
With sulfuric acid |
ethyl 2-formyl-3-oxopropanoate
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With hydrazine dihydrochloride In ethanol at 0 - 20℃; for 32h; | 92% |
With hydrazine In ethanol at 0 - 20℃; for 24h; | 86% |
With hydrazine In ethanol at 0 - 20℃; for 17h; | 72.4% |
With hydrazine In ethanol at 20℃; for 17h; | 72.4% |
4-iodopyrazole
ethanol
carbon monoxide
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With triethylamine at 100℃; for 4h; Inert atmosphere; | 90% |
ethyl 1-(hydroxymethyl)-1H-pyrazole-4-carboxylate
A
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether; methyl fluorosulfonate In tetrahydrofuran Heating; |
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With hydrazine hydrate; acetic acid |
ethyl 2-cyanoacetate
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic anhydride / 5 h / 120 °C 2: hydrazine hydrate / ethanol / 8 h / 0 °C 3: sodium nitrite; acetic acid; hydrogenchloride / water / 0.5 h / 0 °C View Scheme |
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene / 2 h / -50 °C 2: antimony(III) fluoride / N,N-dimethyl-formamide / 1 h / 90 °C 3: acetic acid; hydrogenchloride / 0.5 h / 0 °C View Scheme |
ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid at 0℃; for 0.5h; Reagent/catalyst; |
4-ethoxycarbonylpyrazole
methyl iodide
ethyl 1-methylpyrazole-4-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 85% |
Stage #1: 4-ethoxycarbonylpyrazole With sodium hydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 60 - 65℃; for 6h; | 83% |
4-ethoxycarbonylpyrazole
(2-bromo-5-methyl-1,3-thiazol-4-yl)methanol
ethyl 1-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methyl]-1H-pyrazole-4-carboxylate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; | 100% |
4-ethoxycarbonylpyrazole
ethyl 1-({5-[3-(trifluoromethyl)phenyl]thiophen-2-yl}methyl)-1H-pyrazole-4-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; | 100% |
4-ethoxycarbonylpyrazole
p-methoxybenzyl chloride
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 4h; Reflux; Inert atmosphere; | 100% |
With potassium carbonate In acetonitrile for 4h; Reflux; | 100% |
In acetonitrile at 20℃; for 4h; Reflux; | 99% |
4-ethoxycarbonylpyrazole
methylamine
N-methyl-1H-pyrazole-4-carboxamide
Conditions | Yield |
---|---|
In water at 50 - 55℃; for 4h; Inert atmosphere; | 100% |
In water at 65℃; for 2h; |
4-ethoxycarbonylpyrazole
1-(allyloxy)-2-(chloromethyl)benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 6h; Reflux; | 100% |
4-ethoxycarbonylpyrazole
sodium chlorodifluoroacetate
ethyl 1-(difluoromethyl)-1H-pyrazole-4-carboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; | 100% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 40h; |
4-ethoxycarbonylpyrazole
[3-[N-(tert-butoxycarbonyl)amino]phenyl]methyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Reflux; | 100% |
4-ethoxycarbonylpyrazole
(2-trimethylethylsilylethoxy)methyl chloride
ethyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-4-carboxylate
Conditions | Yield |
---|---|
Stage #1: 4-ethoxycarbonylpyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; | 99.3% |
Stage #1: 4-ethoxycarbonylpyrazole With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 98% |
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 96% |
4-ethoxycarbonylpyrazole
3,5-dibromo-1H-pyrazole-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With bromine; sodium acetate In ethanol at 20℃; for 5h; | 99% |
With bromine; sodium acetate In ethanol; water at 20℃; for 10h; | 92% |
With bromine; sodium acetate In ethanol at 20℃; |
4-ethoxycarbonylpyrazole
dimethylamino sulfonyl chloride
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile for 1h; Inert atmosphere; | 99% |
Stage #1: 4-ethoxycarbonylpyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran; mineral oil at 25℃; for 22h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In tert-butyl alcohol at 80℃; Inert atmosphere; | 99% |
4-ethoxycarbonylpyrazole
2-(tert-butyldimethylsilyloxy)ethyl bromide
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 16h; Cooling with ice; Inert atmosphere; regioselective reaction; | 99% |
4-ethoxycarbonylpyrazole
(1-bromoethyl)benzne
Conditions | Yield |
---|---|
Stage #1: 4-ethoxycarbonylpyrazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: (1-bromoethyl)benzne In N,N-dimethyl-formamide at 20℃; for 2h; | 99% |
2-chloro-6-nitro-4-quinazolone
4-ethoxycarbonylpyrazole
1-(6-nitro-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
In xylenes at 20 - 130℃; for 19h; | 98% |
4-ethoxycarbonylpyrazole
2-chloro-1-{4-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-4-[3,5-di-tert-butyl-4-(3-pyrazol-1-ylpropoxy)phenylsulfanyl]-piperidin-1-yl}ethanone
1-(2-{4-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-4-[3,5-di-tert-butyl-4-(3-pyrazol-1-ylpropoxy)phenylsulfanyl]piperidin-1-yl}-2-oxoethyl)-1H-pyrazole-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-ethoxycarbonylpyrazole; 2-chloro-1-{4-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-4-[3,5-di-tert-butyl-4-(3-pyrazol-1-ylpropoxy)phenylsulfanyl]-piperidin-1-yl}ethanone With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: With ammonium chloride In tetrahydrofuran; mineral oil | 98% |
4-ethoxycarbonylpyrazole
ethyl 1-(3'-cyano-4'-neopentyloxyphenyl)-pyrazol-4-carboxylate
Conditions | Yield |
---|---|
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; regioselective reaction; | 98% |
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 10℃; for 24h; Inert atmosphere; | 98% |
4-chloromethyl-3,5-dimethylisoxazole
4-ethoxycarbonylpyrazole
ethyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; | 97% |
With caesium carbonate In N,N-dimethyl-formamide | 80% |
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; | 80% |
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; | 80% |
4-ethoxycarbonylpyrazole
p-Methoxybenzyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20 - 50℃; for 17h; | 97% |
With potassium carbonate In acetone at 20 - 50℃; for 17h; | 97% |
With potassium carbonate In acetone for 12h; Reflux; |
4-ethoxycarbonylpyrazole
1H-pyrazole-4-carbaldehyde
Conditions | Yield |
---|---|
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃; | 97% |
2-(2-bromoethyl)-2-methyl-1,3-dioxolane
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 65℃; for 2h; Sealed tube; | 97% |
4-ethoxycarbonylpyrazole
Conditions | Yield |
---|---|
With cyanomethylenetributyl-phosphorane In toluene at 100℃; for 6h; | 97% |
4-ethoxycarbonylpyrazole
1H-pyrazole-4-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water for 2h; Reflux; Inert atmosphere; | 96% |
4-ethoxycarbonylpyrazole
xanthene
Conditions | Yield |
---|---|
With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; | 96% |
4-ethoxycarbonylpyrazole
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction; | 96% |
4-ethoxycarbonylpyrazole
2-benzyloxy-3-methylbutanoic acid
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; tert-butylammonium hexafluorophosphate(V) In dichloromethane for 3h; Molecular sieve; Electrochemical reaction; | 96% |
Empirical Formula: C6H8N2O2
Molecular Weight: 140.1399
Nominal Mass: 140 Da
Average Mass: 140.1399 Da
Monoisotopic Mass: 140.058578 Da
Index of Refraction: 1.521
Molar Refractivity: 35.18 cm3
Molar Volume: 115.3 cm3
Surface Tension: 49.2 dyne/cm
Density: 1.214 g/cm3
Flash Point: 122.7 °C
Enthalpy of Vaporization: 54.84 kJ/mol
Boiling Point: 307.8 °C at 760 mmHg
Vapour Pressure: 0.000709 mmHg at 25 °C
Melting point: 78-80 °C(lit.)
Appearance: White to pale yellow crystalline powder
Structure of Ethyl pyrazole-4-carboxylate (CAS NO.37622-90-5):
IUPAC Name: Ethyl 1H-pyrazole-4-carboxylate
Canonical SMILES: CCOC(=O)C1=CNN=C1
InChI: InChI=1S/C6H8N2O2/c1-2-10-6(9)5-3-7-8-4-5/h3-4H,2H2,1H3,(H,7,8)
InChIKey: KACZQOKEFKFNDB-UHFFFAOYSA-N
Product Category of Ethyl pyrazole-4-carboxylate (CAS NO.37622-90-5): Heterocyclic Building Blocks;Pyrazoles
Hazard Codes of Ethyl pyrazole-4-carboxylate (CAS NO.37622-90-5): Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant
Ethyl pyrazole-4-carboxylate , its cas register number is 37622-90-5. It also can be called Ethyl 4-pyrazolecarboxylate ; and 4-Acetylpyrazole .
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