1,3,4-Oxadiazole-2-carboxylicacid, 5-amino-, ethyl ester supplier

Name
5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER
EINECS
CAS No. 4970-53-0
Article Data6
CAS DataBase
Density 1.362 g/cm³
Solubility
Melting Point 199 °C
Formula C₅H₇N₃O₃
Boiling Point 289.1 °C at 760 mmHg
Molecular Weight 157.129
Flash Point 128.6 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Ethyl 5-amino-1,3,4-oxadiazole-2-carboxylate;
PSA 91.24000
LogP 0.40970

Synthetic route

: 506-68-3
bromocyane

: 95-92-1
oxalic acid diethyl ester

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: oxalic acid diethyl ester With hydrazine hydrate In ethanol at -20℃; for 0.5h; Stage #2: bromocyane In ethanol; water at 20℃; for 1h;	31%

: 999-47-3
ethyl 2-(2-carbamoylhydrazono)acetate

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid; sodium acetate / 24 h / 20 °C 2: triethylamine / toluene / 0.17 h / 20 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: bromine; sodium acetate; acetic acid / 24 h / 20 °C 2: triethylamine / toluene / 0.17 h / 20 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: sodium acetate; bromine / acetic acid / 24 h / 20 °C 2: triethylamine / toluene / 0.17 h / 80 °C View Scheme

: 13599-88-7
ethyl 2-bromo-2-(2-carbamoylhydrazono)acetate

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In toluene at 20 - 80℃; for 0.166667h;	1.04 g
With triethylamine In toluene at 20 - 80℃; for 0.166667h;	1.04 g
With triethylamine In toluene at 80℃; for 0.166667h;	1.04 g

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 4970-55-2
5-amino-1,3,4-oxadiazole-2-carboxylic acid amide

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; for 18h; Concentration; Temperature; Solvent; Sealed tube;	99%

: (1R,2R)-2-(4-bromobenzoyl)cyclohexane-1-carboxylic acid

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-({[(1R,2R)-2-(4-bromobenzoyl)cyclohexyl]carbonyl}amino)-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 80℃; for 12h;	98%

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: sodium 5-amino-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
With water; sodium hydroxide for 1h;	82%

: 1780-26-3
2,4-dichloro-2-methylpyrimidine

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-(6-chloro-2-methylpyrimidin-4-ylamino)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	71%

: 6089-09-4
4-pentynoic acid

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-[(pent-4-ynoyl)amino]-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 18h;	70%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 25℃; for 18h;	70%

: 2915-15-3
4-chloro-2-methyl-6-phenyl-pyrimidine

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-(2-methyl-6-phenylpyrimidin-4-ylamino)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	70%

: 24424-99-5
di-tert-butyl dicarbonate

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 1258411-53-8
ethyl 5-[[(tert-butoxy)carbonyl]amino]-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃;	67%
Stage #1: 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 20℃; for 16h;	56.2%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	55%

: 4-chloro-2-methyl-6-(4-nitro-phenyl)-pyrimidine

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-[2-methyl-6-(4-nitrophenyl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	66%

: 4-chloro-2-methyl-6-(3-nitro-phenyl)-pyrimidine

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-[2-methyl-6-(3-nitrophenyl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	61%

: 4-chloro-2-methyl-6-(4-methylpiperazin-1-yl)pyrimidine

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-[2-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	55%
With xantphos; palladium diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	55%

: 74-88-4
methyl iodide

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-((bis(methylthio)methylene)amino)-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With sodium hydroxide In N,N-dimethyl-formamide for 0.166667h; Stage #2: In N,N-dimethyl-formamide for 0.333333h; Stage #3: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;	37%

: 1-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanone

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-[2-methyl-6-(4-acetylpiperazin-1-yl)pyrimidin-4-ylamino][1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	36%
With xantphos; palladium diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	36%

: 127116-19-2
2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 5-{6-[4-(2-hydroxy-ethyl)piperazin-1-yl]-2-methylpyrimidin-4-ylamino}-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	20%
With xantphos; palladium diacetate; sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 36h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	20%

: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-(4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzamido)-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With dmap; trimethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	9%

: 1188-33-6
N,N-dimethylformamide diethyl diacetal

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 37582-75-5
5-(dimethylamino-methyleneamino)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In ethanol

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 916889-45-7
ethyl 5-bromo-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With copper(ll) bromide In acetonitrile at 20℃; for 0.25h; Stage #2: With tert.-butylnitrite In acetonitrile at 20 - 50℃; for 2.5h;

: 925-90-6
ethylmagnesium bromide

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 910656-41-6
3-(5-amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.5h; Mechanism;

: 23719-80-4
cyclopropylmagnesium bromide

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: (5-amino-1,3,4-oxadiazol-2-yl)(dicyclopropyl)methanol

Conditions

Conditions	Yield
Stage #1: cyclopropylmagnesium bromide; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester In tetrahydrofuran at -78 - 20℃; Stage #2: With ammonium chloride In tetrahydrofuran; water

: 925-90-6
ethylmagnesium bromide

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 1-(5-amino-1,3,4-oxadiazol-2-yl)propan-1-one

Conditions

Conditions	Yield
Stage #1: ethylmagnesium bromide; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester In tetrahydrofuran at -78 - 20℃; Stage #2: With ammonium acetate In tetrahydrofuran; water

: 132-60-5
cinchophen

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 1236056-69-1
N-(5-ethoxycarbonyl-1,3,4-oxadiazol-2-yl)-2-phenyl-4-quinolinecarboxamide

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide

: 59661-86-8
2-phenylquinoline-4-carbonyl chloride

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 1236056-69-1
N-(5-ethoxycarbonyl-1,3,4-oxadiazol-2-yl)-2-phenyl-4-quinolinecarboxamide

Conditions

Conditions	Yield
With pyridine at 20 - 60℃;

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 1398750-50-9
Ethyl 5-({[(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinyl]carbonyl}amino)-1,3,4-oxadiazole-2-carboxylate

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: 3775-60-8
1,3,4-oxadiazol-2-amine

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.0833333h;	0.02 g
With water; sodium hydroxide at 20℃; for 0.0833333h;	0.02 g
With sodium hydroxide In water at 20℃; for 0.0833333h;	0.02 g

: 6-(5-chloro-7-methoxy-2,3-diphenylpyrazolo[1,5-a] pyrimidin-6-yl)quinoline

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-((7-oxo-2,3-diphenyl-6-(quinolin-6-yl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-5-yl)amino)-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-((6-chloro-1H-benzo[d]imidazol-2-yl)amino)-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.17 h 1.2: 0.33 h 1.3: 0.5 h / 0 - 20 °C 2.1: N,N-dimethyl-formamide / 16 h / 120 °C View Scheme

: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid

: 4970-53-0
5-amino-1,3,4-oxadiazole-2-carboxylic acid ethyl ester

: ethyl 5-(4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzamido)-1,3,4-oxadiazole-2-carboxylate

B: ethyl 5-(4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzamido)-1,3,4-oxadiazole-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Sealed tube; Stage #2: With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Sealed tube; Overall yield = 9%; Overall yield = 19 mg;	A n/a B n/a

Yield

Stage #1: 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid; 5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Sealed tube;
Stage #2: With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Sealed tube; Overall yield = 9%; Overall yield = 19 mg;

A n/a
B n/a

...Expand

1,3,4-Oxadiazole-2-carboxylicacid, 5-amino-, ethyl ester Specification

The 1,3,4-Oxadiazole-2-carboxylicacid, 5-amino-, ethyl ester is the organic compound with the formula C₅H₇N₃O₃. With the CAS registry number 4970-53-0, its IUPAC name is ethyl 5-amino-1,3,4-oxadiazole-2-carboxylate. The substance should be sealed and stored in dry and well-ventilated place.

Physical properties of 1,3,4-Oxadiazole-2-carboxylicacid, 5-amino-, ethyl ester: (1)ACD/LogP: -0.15; (2)ACD/LogD (pH 5.5): -0.15; (3)ACD/LogD (pH 7.4): -0.15; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 19.86; (7)ACD/KOC (pH 7.4): 19.86; (8)#H bond acceptors: 6; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.525; (12)Molar Refractivity: 35.37 cm³; (13)Molar Volume: 115.3 cm³; (14)Surface Tension: 59.2 dyne/cm; (15)Density: 1.362 g/cm³; (16)Flash Point: 128.6 °C; (17)Enthalpy of Vaporization: 52.84 kJ/mol; (18)Boiling Point: 289.1 °C at 760 mmHg; (19)Vapour Pressure: 0.00224 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOC(=O)C1=NN=C(O1)N
(2)InChI: InChI=1S/C5H7N3O3/c1-2-10-4(9)3-7-8-5(6)11-3/h2H2,1H3,(H2,6,8)
(3)InChIKey: JZSBFOOEPYPCPW-UHFFFAOYSA-N

Product Name

5-AMINO-1,3,4-OXADIAZOLE-2-CARBOXYLIC ACID ETHYL ESTER

Synthetic route

1,3,4-Oxadiazole-2-carboxylicacid, 5-amino-, ethyl ester Specification

Related Products

Hot Products