5-Nitrobenzofuran-2-carboxylic acid supplier

Name
5-Nitrobenzofuran-2-carboxylic acid
EINECS
CAS No. 10242-12-3
Article Data15
CAS DataBase
Density 1.584 g/cm³
Solubility
Melting Point 274 °C
Formula C₉H₅NO₅
Boiling Point 414 °C at 760 mmHg
Molecular Weight 207.142
Flash Point 204.2 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Coumarilicacid, 5-nitro- (6CI);2-Carboxy-5-nitrobenzofuran;5-Nitro-2-benzofurancarboxylic acid;5-Nitrobenzo[b]furan-2-carboxylic acid;5-nitro-1-benzofuran-2-carboxylic acid;
PSA 96.26000
LogP 2.56240

Synthetic route

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

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

Conditions

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran; methanol at 25℃; for 3h;	100%
With water; sodium hydroxide In methanol for 0.5h; Heating;	95%
With methanol; sodium hydroxide for 0.5h;	82%
With potassium hydroxide; phosphoric acid In ethanol; water
With water; sodium hydroxide In tetrahydrofuran; methanol at 70℃; for 1h;

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

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

Conditions

Conditions	Yield
With caesium carbonate; copper dichloride In N,N-dimethyl-formamide at 100℃; for 5h; Solvent; Reagent/catalyst;	85%

: 6965-69-1
2-(2-formyl-4-nitrophenoxy)acetic acid

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

B: 18761-31-4
5-nitrobenzofuran

Conditions

Conditions	Yield
With sodium acetate; acetic anhydride at 110℃; for 3h;	A 73.9% B 25.3%

: 496-41-3
Benzofuran-2-carboxylic acid

A: 69227-70-9
2,6-dinitro-benzofuran

B: 69227-69-6
2,5-dinitrobenzofuran

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

Conditions

Conditions	Yield
With nitric acid; tin(IV) chloride In dichloromethane at 0℃; for 2h;	A 16% B 16% C 39%

...Expand

: 496-41-3
Benzofuran-2-carboxylic acid

A: 33094-66-5
2-nitro-benzofuran

B: 64209-68-3
6-nitro-1-benzofuran-2-carboxylic acid

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

Conditions

Conditions	Yield
With nitric acid; tin(IV) chloride In dichloromethane at 0℃; for 2h;	A 5% B 33% C 33%

...Expand

: 51336-43-7
2-formyl-4-nitrophenoxyacetic acid ethyl ester

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

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

: 104862-16-0, 104862-20-6
(2R,3S)-3-Hydroxy-5-nitro-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester

: 104862-16-0, 104862-20-6
(2S,3S)-3-Hydroxy-5-nitro-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With potassium hydroxide In 1,4-dioxane for 1h; Heating;	A 0.5% B 1% C n/a D n/a
With potassium hydroxide In 1,4-dioxane for 1h; Heating; Yields of byproduct given;	A 0.5% B 1% C n/a D n/a
With potassium hydroxide In 1,4-dioxane for 1h; Heating; Yield given. Yields of byproduct given;	A 0.5% B 1% C n/a D n/a

...Expand

: 5415-73-6
3-bromo-6-nitro-2H-chromen-2-one

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

Conditions

Conditions	Yield
With potassium hydroxide; ethanol

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

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

B: 18761-31-4
5-nitrobenzofuran

Conditions

Conditions	Yield
With potassium hydroxide

: 685-87-0
Diethyl 2-bromomalonate

: 97-51-8
5-Nitrosalicylaldehyde

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

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

Conditions

Conditions	Yield
With potassium carbonate; butanone

...Expand

2-formyl-<4-nitro-phenoxy>-acetic acid: 2-formyl-<4-nitro-phenoxy>-acetic acid

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

Conditions

Conditions	Yield
With sodium acetate; acetic anhydride at 160℃;

: 939-18-4
3-bromo-2H-chromen-2-one

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; HNO3+H2SO4 2: alcohol; KOH-solution View Scheme

: 3199-61-9
ethyl coumarilate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid anhydride; sulfuric acid; nitric acid 2: ethanolic KOH-solution View Scheme

: 97-51-8
5-Nitrosalicylaldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; butanone 2: ethanolic KOH-solution View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 85 °C 2.1: sodium hydroxide; methanol / 0.5 h View Scheme

: 6280-80-4
2-Formylphenoxyacetic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid; nitric acid / 5 - 35 °C 2.1: acetic anhydride / 0.25 h / 35 °C 2.2: 8 h / 125 °C View Scheme

: 90-02-8
salicylaldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 3 h / 30 - 100 °C 2.1: sulfuric acid; nitric acid / 5 - 35 °C 3.1: acetic anhydride / 0.25 h / 35 °C 3.2: 8 h / 125 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 3 h / 30 - 100 °C 2.1: sulfuric acid / water / 0.25 h / 5 - 35 °C 2.2: 2.25 h / 5 - 35 °C 3.1: acetic anhydride / 0.25 h / 35 °C 3.2: 8 h / 125 °C View Scheme

: 6965-69-1
2-(2-formyl-4-nitrophenoxy)acetic acid

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

Conditions

Conditions	Yield
Stage #1: 2-(2-formyl-4-nitrophenoxy)acetic acid With acetic anhydride at 35℃; for 0.25h; Stage #2: With sodium acetate at 125℃; for 8h;
Stage #1: 2-(2-formyl-4-nitrophenoxy)acetic acid With acetic anhydride at 35℃; for 0.25h; Stage #2: With sodium acetate at 125℃; for 8h;

: 2725-81-7
6-nitrocoumarin

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 4 h / Reflux 2: copper dichloride; caesium carbonate / N,N-dimethyl-formamide / 5 h / 100 °C View Scheme

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

: 3196-73-4
methyl 3-aminopropanoate hydrochloride

: C13H12N2O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 48h; Inert atmosphere;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h;

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

: 541-41-3
chloroformic acid ethyl ester

: 90322-48-8
(5-nitro-1-benzofuran-2-yl)methanol

Conditions

Conditions	Yield
With 4-methyl-morpholine; hydrogenchloride; sodium borohydrid In tetrahydrofuran; N,N-dimethyl-formamide	91.2%

: 4518-10-9
Methyl 3-aminobenzoate

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

: methyl 3-(5-nitro-1-benzofuran-2-amido)benzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	86%

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

: 162046-50-6
tert-butyl 2-aminobenzylcarbamate

: tert-butyl N-{[2-(5-nitro-1-benzofuran-2-amido)phenyl]methyl}carbamate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	85%

: 64-17-5
ethanol

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

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

Conditions

Conditions	Yield
With sulfuric acid for 2h; Reflux;	84.2%

: 123-90-0
Thiomorpholin

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

: (5-nitrobenzofuran-2-yl)(thiomorpholino)methanone

Conditions

Conditions	Yield
Stage #1: 5-nitrobenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.25h; Stage #2: Thiomorpholin In N,N-dimethyl-formamide at 20℃;	80%

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

: 28144-70-9
anthranilic acid amide

: N-(2-carbamoylphenyl)-5-nitro-1-benzofuran-2-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	80%

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

: 62-53-3
aniline

: C15H10N2O4

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	79%

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

: 134-20-3
2-carbomethoxyaniline

: methyl 2-(5-nitro-1-benzofuran-2-amido)benzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	78%

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

: 2835-68-9
4-aminobenzamide

: C16H10N2O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	70%

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

: 267644-49-5
5-nitro-1-benzofuran-2-carboxamide

Conditions

Conditions	Yield
Stage #1: 5-nitrobenzofuran-2-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With ammonium hydroxide at 0℃; for 0.166667h;	68%
Stage #1: 5-nitrobenzofuran-2-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 35 - 115℃; Stage #2: With ammonia at 10℃; pH=8 - 9;
Multi-step reaction with 2 steps 1: thionyl chloride / toluene; N,N-dimethyl-formamide / 0.5 h / 70 - 115 °C 2: ammonia / N,N-dimethyl-formamide / 10 °C / pH 8 - 9 View Scheme

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

: 619-45-4
4-methoxycarbonyl aniline

: methyl 4-(5-nitro-1-benzofuran-2-amido)benzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	66%

: 4043-59-8
1,3-diethoxy-isopropanol

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

: 1,3-diethoxypropan-2-yl 5-nitro-1-benzofuran-2-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 50℃; for 14h;	65%

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

: 104862-11-5
5-nitrobenzofuran-2-carboxylic Acid Methyl Ester

: 1646-30-6
methyl 5-acetamidobenzofuran-2-carboxylate

Conditions

Conditions	Yield
With 2-(Dimethylamino)pyridine; acetic anhydride; sodium sulfate; palladium-carbon In water; ethyl acetate; acetone	61%

: 413577-98-7
2-[2-amino-4-(N-tert-butoxycarbonylamino)naphthalen-1-yl]ethyl acetate

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

: 413578-15-1
2-[4-(N-t-butoxycarbonylamino)-2-(5-nitrobenzofuran-2-carboxamido)naphthalen-1-yl]ethyl acetate

Conditions

Conditions	Yield
With pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride	54%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride In pyridine at 20 - 60℃; for 120h;	54%

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

: 3544-24-9
3-Aminobenzamide

: N-(3-carbamoylphenyl)-5-nitro-1-benzofuran-2-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	53%

: 71086-99-2
ethyl 5-amino-1H-indole-2-carboxylate

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

: 266348-99-6
ethyl 5-[(5-nitro-1H-benzofuran-2-ylcarbonyl)amino]-1H-indole-2-carboxylate

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; Acylation;	52%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile

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

: 501-53-1
benzyl chloroformate

: 1277175-54-8
benzyl 5-nitrobenzofuran-2-ylcarbamate

Conditions

Conditions	Yield
With sodium azide; sodium t-butanolate In 1,2-dimethoxyethane at 75℃; for 20h; Curtius rearrangement; Inert atmosphere;	49%

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

: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride

: (R)-(1-(5-nitrobenzofuran-2-carboxamido)-3-methylbutyl)boronic acid

Conditions

Conditions	Yield
Stage #1: 5-nitrobenzofuran-2-carboxylic acid With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 15h; Stage #3: With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; hexane; water at 20℃; for 5h;	48%

Yield

Stage #1: 5-nitrobenzofuran-2-carboxylic acid With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxabor-ol-2-yl]butan-1-amine hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 15h;
Stage #3: With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; hexane; water at 20℃; for 5h;

48%

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

: 2-fluoro-5-nitrobenzofuran

Conditions

Conditions	Yield
With potassium fluoride; Selectfluor In water; 1,2-dichloro-ethane at 70℃;	40%

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

: 413577-26-1
2-(2-amino-4-benzyloxyphenyl)ethyl chloride

: 413577-33-0
2-(4-benzyloxy-2-(5-nitrobenzofuran-2-carboxamido)phenyl)ethyl chloride

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;	22%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h;

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

: C9H14N4O3

: C18H17N5O7

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide Inert atmosphere;	12%

: 67-56-1
methanol

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

: 104862-11-5
5-nitrobenzofuran-2-carboxylic Acid Methyl Ester

Conditions

Conditions	Yield
With hydrogenchloride
Stage #1: 5-nitrobenzofuran-2-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1.66667h; Stage #2: methanol With pyridine In dichloromethane at 0℃; Reagent/catalyst; Solvent;

5-Nitrobenzofuran-2-carboxylic acid Specification

The 5-Nitrobenzofuran-2-carboxylic acid, with the CAS registry number 10242-12-3, is also known as 2-Carboxy-5-nitrobenzofuran. This chemical's molecular formula is C₉H₅NO₅ and molecular weight is 207.14. What's more, its systematic name is 5-nitro-1-benzofuran-2-carboxylic acid.

Physical properties of 5-Nitrobenzofuran-2-carboxylic acid are: (1)ACD/LogP: 2.14; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 6; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 85.26 Å²; (11)Index of Refraction: 1.688; (12)Molar Refractivity: 49.87 cm³; (13)Molar Volume: 130.7 cm³; (14)Polarizability: 19.77×10^-24cm³; (15)Surface Tension: 73.4 dyne/cm; (16)Density: 1.584 g/cm³; (17)Flash Point: 204.2 °C; (18)Enthalpy of Vaporization: 70.31 kJ/mol; (19)Boiling Point: 414 °C at 760 mmHg; (20)Vapour Pressure: 1.35E-07 mmHg at 25°C.

Preparation of 5-Nitrobenzofuran-2-carboxylic acid: this chemical can be prepared by (2-formyl-4-nitro-phenoxy)-acetic acid at the temperature of 110 °C. This reaction will need reagents AcONa, Ac₂O with the reaction time of 3 hours. The yield is about 73.9%.

5-Nitrobenzofuran-2-carboxylic acid can be prepared by (2-formyl-4-nitro-phenoxy)-acetic acid at the temperature of 110 °C

Uses of 5-Nitrobenzofuran-2-carboxylic acid: it can be used to produce 5-[(5-nitro-benzofuran-2-carbonyl)-amino]-1H-indole-2-carboxylic acid ethyl ester at the temperature of 20 °C. It will need reagent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and solvents dimethylformamide, tetrahydrofuran. The yield is about 52%.

5-Nitrobenzofuran-2-carboxylic acid can be used to produce 5-[(5-nitro-benzofuran-2-carbonyl)-amino]-1H-indole-2-carboxylic acid ethyl ester at the temperature of 20 °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. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C=C(O2)C(=O)O
(2)InChI: InChI=1S/C9H5NO5/c11-9(12)8-4-5-3-6(10(13)14)1-2-7(5)15-8/h1-4H,(H,11,12)
(3)InChIKey: LZKWLHXJPIKJSJ-UHFFFAOYSA-N

Product Name

5-Nitrobenzofuran-2-carboxylic acid

Synthetic route

5-Nitrobenzofuran-2-carboxylic acid Specification

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