5-Nitrothiophene-2-carboxylic acid supplier

Name
5-Nitrothiophene-2-carboxylic acid
EINECS 228-654-4
CAS No. 6317-37-9
Article Data35
CAS DataBase
Density 1.676 g/cm³
Solubility
Melting Point 156-159 (Lit.)oC
Formula C₅H₃NO₄S
Boiling Point 367.2 °C at 760 mmHg
Molecular Weight 173.149
Flash Point 175.9 °C
Transport Information
Appearance Pale yellow solid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms 5-Nitro-2-thienylcarboxylic acid;5-Nitro-2-thiophenecarboxylic acid;2-Carboxy-5-nitrothiophene;5-NTCA;NSC 41707;
PSA 111.36000
LogP 1.87770

Synthetic route

: 20898-85-5
(5-nitrothiophen-2-yl)methanol

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

Conditions

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.035h;	99.7%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

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

Conditions

Conditions	Yield
With bromine; sodium acetate; acetic acid	98.5%
With hydrogenchloride; bromine; sodium hydroxide In water	98.2%
With sodium hypobromide; sodium acetate; acetic acid	92%

: 527-72-0
2-thiophenylcarboxylic acid

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

B: 13138-70-0
4-nitro-2-thiophenecarboxylic acid

Conditions

Conditions	Yield
With nitric acid; acetic anhydride; acetic acid at 20℃; for 4h; Nitration;	A 17% B 34%
With sulfuric acid; nitric acid at 0 - 10℃; for 1.25h;
With sulfuric acid; nitric acid at 10 - 20℃;	A n/a B 18.2 g
With sulfuric acid; nitric acid at 10 - 20℃; Overall yield = 18.2 g;

: 16689-02-4
5-nitro-2-thienyl cyanide

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

Conditions

Conditions	Yield
With hydrogenchloride

: 39565-00-9
2-acetyl-5-nitrothiophene

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

B: (5-nitro-[2]thienyl)-glyoxylic acid

Conditions

Conditions	Yield
With nitric acid

: 527-72-0
2-thiophenylcarboxylic acid

: 7697-37-2
nitric acid

: 108-24-7
acetic anhydride

A: 609-40-5
2-nitrothiophene

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

C: 13138-70-0
4-nitro-2-thiophenecarboxylic acid

Conditions

Conditions	Yield
at -5℃;

...Expand

: 527-72-0
2-thiophenylcarboxylic acid

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

B 4-nitro-thiophene-2-carboxylic acid ; 2-nitro-thiophene: 4-nitro-thiophene-2-carboxylic acid ; 2-nitro-thiophene

Conditions

Conditions	Yield
With nitric acid; acetic anhydride at -5℃;

: 63011-97-2
2-thiophenecarboxaldehyde diacetate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid anhydride; nitric acid; acetic acid 2: aqueous sulfuric acid 3: aqueous potassium permanganate solution; aq. NaOH solution View Scheme

: 14289-24-8
5-nitrothiophene-2-carboxaldehyde diacetate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: aqueous potassium permanganate solution; aq. NaOH solution View Scheme
Multi-step reaction with 2 steps 1: ethanol; sulfuric acid 2: chromium (VI)-oxide; aqueous sulfuric acid / 110 °C View Scheme

: 527-72-0
2-thiophenylcarboxylic acid

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

: 7758-19-2
sodium chlorite

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: sodium dihydrogen phosphate

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

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium thiosulfate In water; acetonitrile

...Expand

: 10049-21-5
sodium dihydrogenphosphate

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 7722-84-1
dihydrogen peroxide

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

Conditions

Conditions	Yield
With hydrogenchloride; NaClO2; sodium sulfite In water; acetonitrile

...Expand

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

jones reagent: jones reagent

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

Conditions

Conditions	Yield
In water; isopropyl alcohol; acetone	967 mg (90%)

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

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

Conditions

Conditions	Yield
With oxalyl dichloride Reflux;	100%
With thionyl chloride Reflux;	100%
With thionyl chloride

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

: 64-17-5
ethanol

: 5751-84-8
5-nitro-2-thiophenecarboxylic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride In water for 1.5h; Reflux;	98.3%
Stage #1: 5-nitrothiophene-2-carboxylic acid With thionyl chloride for 3h; Heating / reflux; Stage #2: ethanol for 3h; Heating / reflux;	96%
In methanol Reflux;

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

: 20898-85-5
(5-nitrothiophen-2-yl)methanol

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Cooling with ice;	98%

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

: 4-isopropyl-1-methylcyclohex-3-en-1-amine

: N-(4-isopropyl-1-methylcyclohex-3-en-1-yl)-5-nitrothiophene-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 5-nitrothiophene-2-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane Reflux; Stage #2: 4-isopropyl-1-methylcyclohex-3-en-1-amine With triethylamine In dichloromethane; N,N-dimethyl-formamide Reflux;	96.39%

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

: 154590-66-6
(S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

: C21H22FN5O6S

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	93%

: 67-56-1
methanol

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

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

Conditions

Conditions	Yield
With sulfuric acid for 48h; Heating;	91%
With hydrogenchloride
With thionyl chloride
In methanol Reflux;

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

: 77-78-1
dimethyl sulfate

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

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide); acetone at 100℃; for 1h;	89%

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

: 1118-89-4
diethyl-L-glutamate hydrochloride

: 106585-64-2
N-(5-nitro-2-thiophenecarbonyl)-L-glutamic acid diethyl ester

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 2h; Ambient temperature;	88%

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

: 2-methoxy-6-pentadecylaniline

: N-(2-methoxy-6-pentadecylphenyl)-5-nitrothiophene-2-carboxamide

Conditions

Conditions	Yield
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 2h; Inert atmosphere;	88%

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

: 2-methoxy-6-octylaniline

: N-(2-methoxy-6-octylphenyl)-5-nitrothiophene-2-carboxamide

Conditions

Conditions	Yield
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 2h; Inert atmosphere;	87%

: 864145-50-6
2-{1-[3,5-difluoro-4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-ylmethyl}-isoindole-1,3-dione

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

: 2-(1-{3,5-difluoro-4-[1-(5-nitro-thiophene-2-carbonyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-phenyl}-1H-[1,2,3]triazol-4-ylmethyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: 5-nitrothiophene-2-carboxylic acid With thionyl chloride for 1h; Heating / reflux; Stage #2: 2-{1-[3,5-difluoro-4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-1H-[1,2,3]triazol-4-ylmethyl}-isoindole-1,3-dione With triethylamine In tetrahydrofuran at 0 - 35℃; for 12h;	80%

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

: 16450-41-2
L-glutamic acid diethyl ester

: 106585-64-2
N-(5-nitro-2-thiophenecarbonyl)-L-glutamic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: 5-nitrothiophene-2-carboxylic acid With thionyl chloride for 3h; Reflux; Stage #2: L-glutamic acid diethyl ester With triethylamine In dichloromethane at 0 - 5℃; for 1h;	79.9%

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

: C13H12N4O4S

: 5-nitro-N-(4-(5-(5-nitrothiophen-2-yl)-1,2,4-oxadiazol-3-yl)benzyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	78%

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

: 120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine

: 93988-49-9
N-(3,4-dimethoxyphenethyl)-5-nitrothiophene-2-carboxamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	74%

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

: 4-(4-(tert-butyl)phenyl)-5-(4-fluorophenyl)thiazol-2-amine

: N-(4-(4-(tert-butyl)phenyl)-5-(4-fluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	74%

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

: 89499-38-7
4-amino-2-thiophenecarboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride at 20℃; for 6h; Reduction;	67%

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

: 1601751-76-1
1-(5-nitrothiazol-2-yl)piperidin-4-amine

: 1624309-47-2
5-nitro-N-(1-(5-nitrothiazol-2-yl)piperidin-4-yl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 6h;	65.5%

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

: 1312205-19-8
C14H19ClN2O3

: 1274572-94-9
C19H21N3O7S

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 80℃; for 6h;	64%

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

: 4403-71-8
(4-aminomethyl)aniline

: 5-nitro-N-(4-(5-nitrothiophene-2-carboxamido)benzyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 24h;	63%

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

: 15678-99-6
N-tert-butylchloroacetamide

: 1274572-90-5
C11H14N2O5S

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 80℃; for 6h;	61%

: 5036-48-6
3-(1H-imidazol-1-yl)propan-1-amine

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

: N-(3-(1H-imidazol-1-yl)propyl)-5-nitrothiophene-2-carboxamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	59%

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

: 1312205-12-1
C14H19ClN2O3

: 1274572-93-8
C19H21N3O7S

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 80℃; for 6h;	58%

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

: 3-amino-6-trifluoromethylquinoxaline-2-carbonitrile-N1,N4-dioxide

: 1207614-18-3
C15H6F3N5O5S

Conditions

Conditions	Yield
Stage #1: 5-nitrothiophene-2-carboxylic acid; 3-amino-6-trifluoromethylquinoxaline-2-carbonitrile-N1,N4-dioxide In N,N-dimethyl-formamide at 20℃; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide Stage #3: With dmap	57.9%

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

: 78-95-5
chloroacetone

: 1274572-95-0
C8H7NO5S

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 80℃; for 6h;	56%

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

: 70931-28-1
1-(4-fluorophenylmethyl)piperazine

: [4-(4-fluorobenzyl)piperazin-1-yl](5-nitro-2-thienyl)methanone

Conditions

Conditions	Yield
Stage #1: 5-nitrothiophene-2-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-(4-fluorophenylmethyl)piperazine With triethylamine In N,N-dimethyl-formamide at 50℃; for 0.166667h; Microwave irradiation;	55%

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

: 3-amino-6-trifluoromethylquinoxaline-2-carbonitrile-N1,N4-dioxide

: 1207614-17-2
C15H6F3N5O5S

Conditions

Conditions	Yield
Stage #1: 5-nitrothiophene-2-carboxylic acid; 3-amino-6-trifluoromethylquinoxaline-2-carbonitrile-N1,N4-dioxide In N,N-dimethyl-formamide at 20℃; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide Stage #3: With dmap	51.8%

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

: 13547-70-1
1-chloro-3,3-dimethyl-butan-2-one

: 1274572-97-2
C11H13NO5S

Conditions

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 80℃; for 6h;	48%

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

: C13H10N2O5S

: 5-nitro-N-(4-((5-nitrothiophen-2-yl)carbamoyl)benzyl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With triethylamine; 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 0 - 20℃; for 2h;	46%

5-Nitrothiophene-2-carboxylic acid Chemical Properties

IUPAC Name: 5-Nitrothiophene-2-carboxylic acid
Synonyms of 5-Nitrothiophene-2-carboxylic acid (CAS NO.6317-37-9): 5-Nitro-2-thenoic acid
CAS NO: 6317-37-9
Molecular Formula: C₅H₃NO₄S
Molecular Weight: 173.15
Molecular Structure:
EINECS: 228-654-4
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 100.36 Å²
Index of Refraction: 1.659
Molar Refractivity: 38.11 cm³
Molar Volume: 103.2 cm³
Surface Tension: 79.1 dyne/cm
Density: 1.676 g/cm³
Flash Point: 175.9 °C
Enthalpy of Vaporization: 64.74 kJ/mol
Boiling Point: 367.2 °C at 760 mmHg
Vapour Pressure: 4.88E-06 mmHg at 25°C
SMILES: O=C(O)c1sc([N+](=O)[O-])cc1
InChI: InChI=1/C5H3NO4S/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)
InChIKey: UNEPVPOHGXLUIR-UHFFFAOYAD
Std. InChI: InChI=1S/C5H3NO4S/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)
Std. InChIKey: UNEPVPOHGXLUIR-UHFFFAOYSA-N
Product Categories of 5-Nitrothiophene-2-carboxylic acid (CAS NO.6317-37-9): Heterocycles;Carboxylic Acids;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Carboxylic Acids;Thiophenes & Benzothiophenes;Building Blocks;Heterocyclic Building Blocks;Thiophenes

5-Nitrothiophene-2-carboxylic acid Safety Profile

Hazard Codes: Xi
WGK Germany: 3
Hazard Note: Irritant

Product Name

5-Nitrothiophene-2-carboxylic acid

Synthetic route

5-Nitrothiophene-2-carboxylic acid Chemical Properties

5-Nitrothiophene-2-carboxylic acid Safety Profile

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