Ethyl 5-amino-1-benzofuran-2-carboxylate supplier

Name
ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE
EINECS 1806241-263-5
CAS No. 174775-48-5
Article Data15
CAS DataBase
Density 1.259 g/cm³
Solubility
Melting Point 54-56 °C
Formula C₁₁H₁₁NO₃
Boiling Point 348.067 °C at 760 mmHg
Molecular Weight 205.213
Flash Point 164.306 °C
Transport Information
Appearance
Safety
Risk Codes Xi:;
Molecular Structure
Hazard Symbols Xi
Synonyms 5-Aminobenzofuran-2-carboxylicacid ethyl ester;Ethyl 5-aminobenzofuran-2-carboxylate;ethyl 5-amino-1-benzofuran-2-carboxylate;
PSA 65.46000
LogP 2.77290

Synthetic route

: 69604-00-8
ethyl 5-nitrobenzo[d]furan-2-carboxylate

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 33 - 38℃; under 3000.3 - 3750.38 Torr;	100%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 33 - 38℃; under 3000.3 - 3750.38 Torr;	100%
With hydrogen In ethyl acetate; N,N-dimethyl-formamide under 760.051 Torr; for 4h; Heating; Flow reactor; Green chemistry;	99%

: 90-02-8
salicylaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
With hydrogen In ethanol at 20℃; for 6h;	91%
Multi-step reaction with 3 steps 1: nitric acid / acetic acid 2: sodium carbonate / 1-methyl-pyrrolidin-2-one 3: hydrogen View Scheme

: 97-51-8
5-Nitrosalicylaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 85 - 90 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 33 - 38 °C / 3000.3 - 3750.38 Torr View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / 1-methyl-pyrrolidin-2-one 2: hydrogen View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 30 - 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 33 - 38 °C / 3000.3 - 3750.38 Torr View Scheme

: 2725-81-7
6-nitrocoumarin

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine / chloroform / 0 - 20 °C 2.1: 1 h / Reflux 2.2: 8 h / Reflux 3.1: hydrogen; 5%-palladium/activated carbon / ethanol / 3 h / 10 - 30 °C / 2250.23 - 3750.38 Torr View Scheme
Multi-step reaction with 4 steps 1: bromine / chloroform / 0 - 20 °C 2: 1 h / Reflux 3: triethylamine / ethanol / 8 h / Reflux 4: hydrogen; 5%-palladium/activated carbon / ethanol / 3 h / 10 - 30 °C / 2250.23 - 3750.38 Torr View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / ethanol; water / 4 h / Reflux 2: copper dichloride; caesium carbonate / N,N-dimethyl-formamide / 5 h / 100 °C 3: sulfuric acid / 2 h / Reflux 4: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 30 °C / 3000.3 - 3750.38 Torr View Scheme

: 3,4-dibromo-6-nitrochroman-2-one

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1 h / Reflux 1.2: 8 h / Reflux 2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 3 h / 10 - 30 °C / 2250.23 - 3750.38 Torr View Scheme
Multi-step reaction with 3 steps 1: 1 h / Reflux 2: triethylamine / ethanol / 8 h / Reflux 3: hydrogen; 5%-palladium/activated carbon / ethanol / 3 h / 10 - 30 °C / 2250.23 - 3750.38 Torr View Scheme

: 50396-49-1
3-(2-hydroxy-5-nitrophenyl)acrylic acid

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: copper dichloride; caesium carbonate / N,N-dimethyl-formamide / 5 h / 100 °C 2: sulfuric acid / 2 h / Reflux 3: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 30 °C / 3000.3 - 3750.38 Torr View Scheme

: 10242-12-3
5-nitrobenzofuran-2-carboxylic acid

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 2 h / Reflux 2: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 30 °C / 3000.3 - 3750.38 Torr View Scheme

: C17H27NO3Si2

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride In chloroform; water for 1h;	63.3 mg

: (2S,3S)-1-(tert-butoxycarbonyl)-3-(2-methylphenyl)pyrrolidine-2-carboxylic acid

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: tert-butyl (2S,3S)-2-{[2-(ethoxycarbonyl)-1-benzofuran-5-yl]carbamoyl}-3-(2-methylphenyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (2S,3S)-1-(tert-butoxycarbonyl)-3-(2-methylphenyl)pyrrolidine-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: ethyl 5-amino-1-benzofuran-2-carboxylate In N,N-dimethyl-formamide at 20 - 70℃; for 5h;	99%

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: C11H9(2)H2NO3

Conditions

Conditions	Yield
With C40H51ClIrN3; potassium carbonate; deuterium In dichloromethane at 50℃; under 760.051 Torr; for 12h; Sealed tube; Inert atmosphere; regioselective reaction;	96%

: 77716-11-1
4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: C22H25N3O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide	90%

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 1122-91-4
4-bromo-benzaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 13-(4-bromophenyl)-12-oxo-6,13-dihydro-12H-chromeno[4,3-b]furo[3,2-f]quinoline-2-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 6h;	90%

...Expand

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: 1418125-60-6
C10H8N2O3

Conditions

Conditions	Yield
With sodium methylate at 20℃; for 6h;	86%

: 3859-41-4
1,3-cyclopentadione

: 83-38-5
2,6-dichlorobenzaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 10-(2,6-dichlorophenyl)-9-oxo-7,8,9,10-tetrahydro-6H-cyclopenta[b]furo[3,2-f]quinoline-2-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 8h;	86%

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 104-88-1
4-chlorobenzaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 13-(4-chlorophenyl)-12-oxo-6,13-dihydro-12H-chromeno[4,3-b]furo[3,2-f]quinoline-2-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 6h;	85%

...Expand

: 821-48-7
bis-(2-chloroethyl)amine hydrochloride

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: 5-(piperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 50 - 60℃; for 4h;	85%
With sodium carbonate In ethanol at 50 - 60℃; for 4h;	83.1%

: 3859-41-4
1,3-cyclopentadione

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 10-(3,4-dimethoxyphenyl)-9-oxo-7,8,9,10-tetrahydro-6H-cyclopenta[b]furo[3,2-f]quinoline-2-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 10h;	84%

...Expand

: tetrafluoroboric acid

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: 1618107-87-1
2‐(ethoxycarbonyl)‐1‐benzofuran‐5‐diazonium tetrafluoroborate

Conditions

Conditions	Yield
Stage #1: tetrafluoroboric acid; ethyl 5-amino-1-benzofuran-2-carboxylate In ethanol; water at 20℃; for 0.0333333h; Stage #2: With tert.-butylnitrite In ethanol; water at 0 - 20℃; for 1.25h;	83%

: 67393-83-3, 67393-84-4, 67663-02-9, 91603-21-3, 91603-22-4, 118759-60-7, 118759-61-8
2-((2RS,3RS)-3-ethyloxiran-2-yl)ethan-1-ol

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: C17H23NO5

Conditions

Conditions	Yield
With 3,4,5-trifluorophenylboronic acid In toluene at 60℃; for 24h; regioselective reaction;	83%

: 3859-41-4
1,3-cyclopentadione

: 874-42-0
2,4-dichlorobenzaldeyhde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 10-(2,4-dichlorophenyl)-9-oxo-7,8,9,10-tetrahydro-6H-cyclopenta[b]furo[3,2-f]quinoline-2-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 8h;	82%

...Expand

: 821-48-7
bis-(2-chloroethyl)amine hydrochloride

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-(1-piperazinyl)benzofuran-2-carboxylate dihydrochloride

Conditions

Conditions	Yield
Stage #1: bis-(2-chloroethyl)amine hydrochloride; ethyl 5-amino-1-benzofuran-2-carboxylate With tetrabutylammomium bromide; potassium carbonate In o-xylene at 135 - 140℃; for 32h; Stage #2: With hydrogenchloride In dichloromethane; water	81.3%
Stage #1: bis-(2-chloroethyl)amine hydrochloride; ethyl 5-amino-1-benzofuran-2-carboxylate With tetrabutylammomium bromide; potassium carbonate In o-xylene at 20 - 140℃; for 32h; Stage #2: With hydrogenchloride In dichloromethane; water	81.3%

: 821-48-7
bis-(2-chloroethyl)amine hydrochloride

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: 1469427-45-9
ethyl 5-(1-piperazinyl)benzofuran-2-carboxylate hydrobromide

Conditions

Conditions	Yield
Stage #1: bis-(2-chloroethyl)amine hydrochloride; ethyl 5-amino-1-benzofuran-2-carboxylate With tetrabutylammomium bromide; potassium carbonate In o-xylene at 135 - 140℃; for 32h; Stage #2: With hydrogen bromide In dichloromethane; water	81.3%

: 821-48-7
bis-(2-chloroethyl)amine hydrochloride

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-(1-piperazinyl)benzofuran-2-carboxylate hydrobromide

Conditions

Conditions	Yield
Stage #1: bis-(2-chloroethyl)amine hydrochloride; ethyl 5-amino-1-benzofuran-2-carboxylate With tetrabutylammomium bromide; potassium carbonate In o-xylene at 20 - 140℃; for 32h; Stage #2: With hydrogen bromide In dichloromethane; water	81.3%

: 3859-41-4
1,3-cyclopentadione

: 104-88-1
4-chlorobenzaldehyde

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 10-(4-chlorophenyl)-9-oxo-7,8,9,10-tetrahydro-6H-cyclopenta[b]furo[3,2-f] quinoline-2-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 8h;	79%

...Expand

: 1626-05-7
Phenyl-vinyl-glykolsaeure

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: C21H17NO4

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In acetonitrile at 25℃; for 12h;	73%

: 124-63-0
methanesulfonyl chloride

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-(methylsulfonamido)benzofuran-2-carboxylate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; for 3h;	72%

: 13675-18-8
tetrahydroxydiboron

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: 1618107-90-6
2-(ethoxycarbonyl)benzofuran-5-ylboronic acid

Conditions

Conditions	Yield
Stage #1: ethyl 5-amino-1-benzofuran-2-carboxylate With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h; Stage #2: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;	70.5%

: 64-19-7
acetic acid

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-acetamidobenzofuran-2-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 15h;	66%

: 2926-29-6
Langlois reagent

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-isothiocyanatobenzofuran-2-carboxylate

Conditions

Conditions	Yield
With copper(l) iodide; phosphonic acid diethyl ester In toluene at 110℃; for 16h; Schlenk technique; Green chemistry;	61%

: 101-02-0
triphenyl phosphite

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-(diphenoxyphosphoryl)benzofuran-2-carboxylate

Conditions

Conditions	Yield
With tert.-butylnitrite; toluene-4-sulfonic acid In acetonitrile at 0 - 20℃; for 8h;	59%
Stage #1: ethyl 5-amino-1-benzofuran-2-carboxylate With tert.-butylnitrite; toluene-4-sulfonic acid In acetonitrile at 0℃; for 8h; Sandmeyer Reaction; Stage #2: triphenyl phosphite In acetonitrile at 0.25℃; for 8h; Sandmeyer Reaction;	58%

: 201230-82-2
carbon monoxide

: cyclobutanone O-(4-(trifluoromethyl)benzoyl) oxime

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: C16H16N2O4

Conditions

Conditions	Yield
With copper(l) chloride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine at 20℃; Irradiation; chemoselective reaction;	57%

...Expand

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: trifluoromethylsilver

: 575469-30-6
ethyl 5-(trifluoromethyl)benzofuran-2-carboxylate

Conditions

Conditions	Yield
Stage #1: ethyl 5-amino-1-benzofuran-2-carboxylate With hydrogenchloride In water at 0℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: With tert.-butylnitrite at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #3: trifluoromethylsilver at -78 - 20℃; for 4h; Inert atmosphere; Schlenk technique;	55%
Stage #1: ethyl 5-amino-1-benzofuran-2-carboxylate With hydrogenchloride In water at 0℃; for 0.0833333h; Sandmeyer Reaction; Schlenk technique; Stage #2: With tert.-butylnitrite In water at -196 - 20℃; Sandmeyer Reaction; Schlenk technique; Inert atmosphere; Stage #3: trifluoromethylsilver In water at -78 - 20℃; for 5h; Sandmeyer Reaction; Schlenk technique; Inert atmosphere;	55%

: Se-(difluoromethyl) 4-methylbenzenesulfonoselenoate

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: ethyl 5-((difluoromethyl)selanyl)benzofuran-2-carboxylate

Conditions

Conditions	Yield
Stage #1: ethyl 5-amino-1-benzofuran-2-carboxylate With rose bengal; toluene-4-sulfonic acid In dimethyl sulfoxide for 0.0833333h; Sealed tube; Stage #2: Se-(difluoromethyl) 4-methylbenzenesulfonoselenoate With tert.-butylnitrite In dimethyl sulfoxide at 20℃; for 10h; Irradiation;	51%

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: 93849-31-1
ethyl 5-fluoro-1H-benzofuran-2-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1h;	45%

: 174775-48-5
ethyl 5-amino-1-benzofuran-2-carboxylate

: C11H10(2)HNO3

Conditions

Conditions	Yield
With chloro(cycloocta-1,5-diene)(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)iridium; deuterium In dichloromethane at 50℃; under 760.051 Torr; for 12h; Reagent/catalyst; Sealed tube; Inert atmosphere; regioselective reaction;	45%

Ethyl 5-amino-1-benzofuran-2-carboxylate Specification

The 2-Benzofurancarboxylicacid, 5-amino-, ethyl ester, with the CAS registry number 174775-48-5, has the systematic name of ethyl 5-amino-1-benzofuran-2-carboxylate. It belongs to the following product categoies: Aminoacid; Esters; Furans, Benzofurans & Dihydrobenzofurans. And the molecular formula of this chemical is C₁₁H₁₁NO₃.

The physical properties of 2-Benzofurancarboxylicacid, 5-amino-, ethyl ester are as followings: (1)ACD/LogP: 2.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 13; (6)ACD/BCF (pH 7.4): 13; (7)ACD/KOC (pH 5.5): 218; (8)ACD/KOC (pH 7.4): 219; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 65.46 Å²; (13)Index of Refraction: 1.617; (14)Molar Refractivity: 57.037 cm³; (15)Molar Volume: 163.024 cm³; (16)Polarizability: 22.611×10^-24cm³; (17)Surface Tension: 50.952 dyne/cm; (18)Density: 1.259 g/cm³; (19)Flash Point: 164.306 °C; (20)Enthalpy of Vaporization: 59.241 kJ/mol; (21)Boiling Point: 348.067 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)c2oc1ccc(cc1c2)N
(2)InChI: InChI=1/C11H11NO3/c1-2-14-11(13)10-6-7-5-8(12)3-4-9(7)15-10/h3-6H,2,12H2,1H3
(3)InChIKey: YFFLLDHEEWSHQG-UHFFFAOYAK

Product Name

ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE

Synthetic route

Ethyl 5-amino-1-benzofuran-2-carboxylate Specification

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