5-Aminothiophene-2-carboxylic acid methyl ester supplier

Name
5-Amino-thiophene-2-carboxylic acid methyl ester
EINECS 200-110-4
CAS No. 14597-58-1
Article Data18
CAS DataBase
Density 1.319g/cm³
Solubility
Melting Point 81 °C
Formula C₆H₇NO₂S
Boiling Point 304.8 °C at 760 mmHg
Molecular Weight 157.193
Flash Point 138.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-Aminothiophene-2-carboxylicacid methyl ester;Methyl 5-amino-2-thiophenecarboxylate;
PSA 80.56000
LogP 1.69810

Synthetic route

: 5832-01-9
methyl 5-nitrothiophene-2-carboxylate

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h;	100%
With hydrogen; palladium 10% on activated carbon In ethanol under 760.051 Torr;	92%
Stage #1: methyl 5-nitrothiophene-2-carboxylate With hydrogenchloride; tin(ll) chloride In ethanol; water at 20 - 35℃; for 2h; Stage #2: In water pH=9; basic conditions;	66%

: 67-56-1
methanol

: 527-72-0
2-thiophenylcarboxylic acid

A: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

B: 89499-43-4
methyl 4-aminothiophene-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-thiophenylcarboxylic acid With sulfuric acid; nitric acid at 0 - 10℃; for 1.25h; Stage #2: methanol With thionyl chloride at 20℃; Reflux;	A 8.5% B 31%

...Expand

: 6317-37-9
5-nitrothiophene-2-carboxylic acid

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: Fe; AcOH View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / 1,2-dichloro-ethane / 0.5 h / 150 °C / Microwave irradiation 2: dichloromethane / 0 - 20 °C 3: 20 % Pd(OH)2/C; hydrogen / ethanol View Scheme
Multi-step reaction with 2 steps 1: methanol / Reflux 2: ammonium formate; zinc / ethanol; ethyl acetate View Scheme

: 5832-01-9
methyl 5-nitrothiophene-2-carboxylate

: 7439-89-6
iron

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

Conditions

Conditions	Yield
In methanol; water

: 527-72-0
2-thiophenylcarboxylic acid

A: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

B: 89499-43-4
methyl 4-aminothiophene-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-thiophenylcarboxylic acid With sulfuric acid; nitric acid at 0 - 10℃; Stage #2: With methanol; thionyl chloride at 20℃; Reflux; Stage #3: With hydrogenchloride; iron; ammonium chloride In methanol; water at 20 - 70℃;

: 39978-57-9
5-nitrothiophene-2-carbonyl chloride

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 0 - 20 °C 2: 20 % Pd(OH)2/C; hydrogen / ethanol View Scheme

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 4869-46-9
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

: 1177471-31-6
C13H13N3O4S

Conditions

Conditions	Yield
With acetic acid for 6h; Reflux;	94%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 1094070-49-1
C17H25N5O3SSi

: 1094071-35-8
C22H28N6O3SSi

Conditions

Conditions	Yield
Stage #1: methyl 5-aminothiophene-2-carboxylate; C17H25N5O3SSi With sodium hydride In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: With water; ammonium chloride In dimethyl sulfoxide	85%
With sodium hydride In N,N-dimethyl-formamide at 20℃;

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 372-31-6
ethyl 4,4,4-trifluoroacetoacetate

: 380419-63-6
2-carbomethoxy-4-trifluoromethylthieno[2,3-b]pyridin-6-one

Conditions

Conditions	Yield
In acetic acid Heating;	84%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 326-91-0
1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione

: 6-thiophen-2-yl-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In acetic acid Heating;	78%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 126855-73-0
N-(1-chloro-2,2,2-trifluoroethylidene)-O-methylurethane

: 5-{2,2,2-Trifluoro-1-[(Z)-methoxycarbonylimino]-ethylamino}-thiophene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In benzene at 20℃; for 2h;	78%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 105161-33-9
3,3-dimethoxy-2-formyl-propanenitrile sodium salt

: methyl 5-cyanothieno[2,3-b]pyridine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl 5-aminothiophene-2-carboxylate; 3,3-dimethyloxy-2-formylpropionitrile sodium salt With hydrogenchloride In methanol; water at 20℃; for 4h; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 12h;	78%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: C9H8BrF2NO2

: 1314091-77-4
methyl 5-(3-(difluoromethoxy)-2-nitrophenylamino)thiophene-2-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80 - 90℃; for 0.25h; Inert atmosphere;	77.5%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 1000339-52-5
3-fluoro-2-nitrobenzonitrile

: 1314092-14-2
methyl 5-(3-cyano-2-nitrophenylamino)thiophene-2-carboxylate

Conditions

Conditions	Yield
With triethylbutylammonium chloride; potassium hydroxide In N,N-dimethyl-formamide Cooling with ice;	77%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 326-06-7
1-Phenyl-4,4,4-trifluorobutane-1,3-dione

: 6-phenyl-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In acetic acid Heating;	73%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 111335-09-2
methyl N-(1,2,2,2-tetrachloroethylidene)urethan

: 5-{2,2,2-Trichloro-1-[(Z)-methoxycarbonylimino]-ethylamino}-thiophene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In benzene at 20℃; for 2h;	73%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

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

: 666853-39-0
methyl 5-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate

Conditions

Conditions	Yield
In tetrahydrofuran for 48h; Reflux;	68%
In tetrahydrofuran for 72h; Heating / reflux;
at 110℃; for 1.5h; Inert atmosphere;

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 870072-76-7
2-(2-tert-butylphenoxy)-3-isocyanatopyridine

: methyl 5-(3-(2-(2-(tert-butyl)phenoxy)pyridin-3-yl)ureido)thiophene-2-carboxylate

Conditions

Conditions	Yield
In toluene at 80℃; for 1.5h; Microwave irradiation;	63%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 116436-11-4
N-(2-bromo-6-methylphenyl)acetamide

: methyl 5-(2,4-dimethyl-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; bis(2',6'-diisopropoxybiphenyl)cyclohexylphosphine In tert-butyl alcohol at 120℃; for 2h; Molecular sieve; Microwave irradiation;	61%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 322474-21-5, 107819-90-9
1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea

: methyl 5-{[(1E)-{[(tert-butoxy)carbonyl]amino}({[(tert-butoxy)carbonyl]imino}) methyl]amino}thiophene-2-carboxylate

Conditions

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃;	53%
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃;

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 41890-17-9
(N-methyl)benzimidoyl chloride

: 380416-72-8
2-methoxycarbonyl-5-(α-methylaminobenzylidene)aminothiophene

Conditions

Conditions	Yield
With triethylamine In benzene at 25℃; for 12h;	47%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 2009-81-6
2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate

: methyl 5-formylthieno[2,3-b]pyridine-2-carboxylate

Conditions

Conditions	Yield
With sodium methylate In methanol for 12h; Reflux;	43%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: tert-butyl N-[(tert-butoxy)carbonyl]-N-(6-chloro-4-methylpyridazin-3-yl)carbamate

: methyl 5-[(6-{bis[(tert-butoxy)carbonyl]amino}-5-methylpyridazin-3-yl)amino]thiophene-2-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 100℃; Inert atmosphere;	41%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 1-[(tert-butoxy)carbonyl]-4-[(dimethylamino)methyl]piperidine-4-carboxylic acid

: tert-butyl 4-[(dimethylamino)methyl]-4-{[5-(methoxycarbonyl)thiophen-2-yl]carbamoyl}piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-[(tert-butoxy)carbonyl]-4-[(dimethylamino)methyl]piperidine-4-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 0.5h; Stage #2: methyl 5-aminothiophene-2-carboxylate In N,N-dimethyl-formamide at 30℃; for 18h;	39%

: 910472-18-3
2-amino-4,5,6,7,8,9-hexahydro-cycloocta[b]thiophene-3-carboxylic acid isopropyl ester

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 32315-10-9
bis(trichloromethyl) carbonate

: 2-[3-(3-methoxycarbonyl-thiophen-2-yl)-ureido]-4,5,6,7,8,9-hexahydro-cycloocta[b]thiophene-3-carboxylic acid isopropyl ester

Conditions

Conditions	Yield
Stage #1: 2-amino-4,5,6,7,8,9-hexahydro-cycloocta[b]thiophene-3-carboxylic acid isopropyl ester; bis(trichloromethyl) carbonate With triethylamine In dichloromethane at 20℃; for 2h; Stage #2: methyl 5-aminothiophene-2-carboxylate In dichloromethane at 20℃; for 1h;	27%

...Expand

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: racemic (2'R,3R,3'S,5'S)-6-chloro-3'-(3-chloro-2-fluoro-phenyl)-5'-(2-cyano-2-methyl-propyl)-2-oxo-spiro[indoline-3,4'-pyrrolidine]-2'-carboxylic acid

: methyl rac-5-[[(2'R,3R,3'S,5'S)-6-chloro-3'-(3-chloro-2-fluoro-phenyl)-5'-(2-cyano-2-methyl-propyl)-2-oxo-spiro[indoline-3,4'-pyrrolidine]-2'-carbonyl]amino]thiophene-2-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	8.7%

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 5-benzoylimino-4,5-dihydro-thiophene-2-carboxylic acid methyl ester

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 3173-56-6
benzyl isothiocyanate

: 304696-16-0
5-(3-benzyl-ureido)-thiophene-2-carboxylic acid methyl ester

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 4-oxo-2-trichloromethyl-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / Et3N / benzene / 2 h / 20 °C 2: 79 percent / toluene / 3 h / 110 °C View Scheme

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 4-oxo-2-trifluoromethyl-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / Et3N / benzene / 2 h / 20 °C 2: 76 percent / toluene / 3 h / 110 °C View Scheme

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: C10H5Cl2F3NO4PS

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / acetic acid / Heating 2: POCl3 / 3 h / Heating View Scheme

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 2-carbomethoxy-4-trifluoromethylthieno[2,3-b]pyridin-6-yl dimethylphosphate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / acetic acid / Heating 2: POCl3 / 3 h / Heating 3: Et3N / benzene / 1.5 h / 20 °C View Scheme

: 14597-58-1
methyl 5-aminothiophene-2-carboxylate

: 6-pyrrolidin-1-yl-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / acetic acid / Heating 2: 73 percent / Et3N / dioxane / 16 h / Heating 3: 75 percent / i-Pr2NEt / dioxane / Heating View Scheme

5-Aminothiophene-2-carboxylic acid methyl ester Specification

The 5-Aminothiophene-2-carboxylic acid methyl ester, with cas registry number 14597-58-1, has the systematic name of methyl 5-aminothiophene-2-carboxylate. And its IUPAC name is the same one. Besides this, it is also called 2-thiophenecarboxylic acid, 5-amino-, methyl ester.

Physical properties about this chemical are: (1)ACD/LogP: 0.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.62; (4)ACD/LogD (pH 7.4): 0.62; (5)ACD/BCF (pH 5.5): 1.73; (6)ACD/BCF (pH 7.4): 1.73; (7)ACD/KOC (pH 5.5): 51.52; (8)ACD/KOC (pH 7.4): 51.52; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 57.78 Å²; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 40.64 cm³; (15)Molar Volume: 119 cm³; (16)Polarizability: 16.11×10^-24cm³; (17)Surface Tension: 52.8 dyne/cm; (18)Enthalpy of Vaporization: 54.52 kJ/mol; (19)Vapour Pressure: 0.000855 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1sc(N)cc1
(2)InChI: InChI=1/C6H7NO2S/c1-9-6(8)4-2-3-5(7)10-4/h2-3H,7H2,1H3
(3)InChIKey: NNQTUMGJWXJMIR-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C6H7NO2S/c1-9-6(8)4-2-3-5(7)10-4/h2-3H,7H2,1H3
(5)Std. InChIKey: NNQTUMGJWXJMIR-UHFFFAOYSA-N

Product Name

5-Amino-thiophene-2-carboxylic acid methyl ester

Synthetic route

5-Aminothiophene-2-carboxylic acid methyl ester Specification

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