10242-12-3

Basic information

• Product Name: 5-NITROBENZOFURAN-2-CARBOXYLIC ACID
• Synonyms: BUTTPARK 40\07-63;5-NITROBENZO[B]FURAN-2-CARBOXYLIC ACID;5-NITROBENZOFURAN-2-CARBOXYLIC ACID;5-NITRO-1-BENZOFURAN-2-CARBOXYLIC ACID;5-Nitrobenzofuran-2-carboxylic acid ,98%;2-Carboxy-5-nitrobenzofuran;5-Nitro-2-benzofurancarboxylic acid;5-Nitrobenzofuran-2-carboxylic acid 97%
• CAS NO: 10242-12-3
• Molecular Formula: C₉H₅NO₅
• Molecular Weight: 207.14
• Product Categories: Benzofurans;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 10242-12-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 274 °C
• Boiling Point: 414 °C at 760 mmHg
• Flash Point: 204.2 °C
• Appearance: /
• Density: 1.584 g/cm³
• Vapor Pressure: 1.35E-07mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.77±0.30(Predicted)
• CAS DataBase Reference: 5-NITROBENZOFURAN-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROBENZOFURAN-2-CARBOXYLIC ACID(10242-12-3)
• EPA Substance Registry System: 5-NITROBENZOFURAN-2-CARBOXYLIC ACID(10242-12-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 10242-12-3(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

Different sources of media describe the Uses of 10242-12-3 differently. You can refer to the following data:
1. 5-Nitro-benzofuran-2-carboxylic Acid is a reagent used in the synthesis of arylamidobenzofurans.
2. Reactant for:? ;Preparation of arylarylamidobenzofurans via Curtius rearrangement followed by bromination and Suzuki reaction1? ;Synthesis and antibacterial evaluation of nitazoxanide-based analogs2? ;Preparation of Melanin-Concentrating Hormone Receptor 1 antagonist3? ;Synthesis of benzoyl and cinnamoyl nitrogen mustard derivatives of benzoheterocyclic analogs of tallimustine as antitumor agents4

InChI:InChI=1/C9H5NO5/c11-9(12)8-4-5-3-6(10(13)14)1-2-7(5)15-8/h1-4H,(H,11,12)/p-1

Synthetic route

ethyl 5-nitrobenzo[d]furan-2-carboxylate (69604-00-8) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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;

3-(2-hydroxy-5-nitrophenyl)acrylic acid (50396-49-1) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

2-(2-formyl-4-nitrophenoxy)acetic acid (6965-69-1) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 5-nitrobenzofuran (18761-31-4)

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

Benzofuran-2-carboxylic acid (496-41-3) → 2,6-dinitro-benzofuran (69227-70-9) + 2,5-dinitrobenzofuran (69227-69-6) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

Benzofuran-2-carboxylic acid (496-41-3) → 2-nitro-benzofuran (33094-66-5) + 6-nitro-1-benzofuran-2-carboxylic acid (64209-68-3) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

2-formyl-4-nitrophenoxyacetic acid ethyl ester (51336-43-7) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + ethyl 5-nitrobenzo[d]furan-2-carboxylate (69604-00-8) + (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 (104862-16-0, 104862-20-6)

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

3-bromo-6-nitro-2H-chromen-2-one (5415-73-6) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

Conditions	Yield
With potassium hydroxide; ethanol

ethyl 5-nitrobenzo[d]furan-2-carboxylate (69604-00-8) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 5-nitrobenzofuran (18761-31-4)

Conditions	Yield
With potassium hydroxide

Diethyl 2-bromomalonate (685-87-0) + 5-Nitrosalicylaldehyde (97-51-8) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + ethyl 5-nitrobenzo[d]furan-2-carboxylate (69604-00-8)

Conditions	Yield
With potassium carbonate; butanone

2-formyl-<4-nitro-phenoxy>-acetic acid → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

3-bromo-2H-chromen-2-one (939-18-4) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

ethyl coumarilate (3199-61-9) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

5-Nitrosalicylaldehyde (97-51-8) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

2-Formylphenoxyacetic acid (6280-80-4) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

salicylaldehyde (90-02-8) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

2-(2-formyl-4-nitrophenoxy)acetic acid (6965-69-1) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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;

6-nitrocoumarin (2725-81-7) → 5-nitrobenzofuran-2-carboxylic acid (10242-12-3)

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + methyl 3-aminopropanoate hydrochloride (3196-73-4) → C13H12N2O6

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;

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + chloroformic acid ethyl ester (541-41-3) → (5-nitro-1-benzofuran-2-yl)methanol (90322-48-8)

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

Methyl 3-aminobenzoate (4518-10-9) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → methyl 3-(5-nitro-1-benzofuran-2-amido)benzoate

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + tert-butyl 2-aminobenzylcarbamate (162046-50-6) → tert-butyl N-{[2-(5-nitro-1-benzofuran-2-amido)phenyl]methyl}carbamate

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

ethanol (64-17-5) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → ethyl 5-nitrobenzo[d]furan-2-carboxylate (69604-00-8)

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

Thiomorpholin (123-90-0) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → (5-nitrobenzofuran-2-yl)(thiomorpholino)methanone

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%

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + anthranilic acid amide (28144-70-9) → N-(2-carbamoylphenyl)-5-nitro-1-benzofuran-2-carboxamide

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + aniline (62-53-3) → C15H10N2O4

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 2-carbomethoxyaniline (134-20-3) → methyl 2-(5-nitro-1-benzofuran-2-amido)benzoate

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 4-aminobenzamide (2835-68-9) → C16H10N2O6

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → 5-nitro-1-benzofuran-2-carboxamide (267644-49-5)

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-(5-nitro-1-benzofuran-2-amido)benzoate

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

1,3-diethoxy-isopropanol (4043-59-8) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → 1,3-diethoxypropan-2-yl 5-nitro-1-benzofuran-2-carboxylate

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%

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 5-nitrobenzofuran-2-carboxylic Acid Methyl Ester (104862-11-5) → methyl 5-acetamidobenzofuran-2-carboxylate (1646-30-6)

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

2-[2-amino-4-(N-tert-butoxycarbonylamino)naphthalen-1-yl]ethyl acetate (413577-98-7) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → 2-[4-(N-t-butoxycarbonylamino)-2-(5-nitrobenzofuran-2-carboxamido)naphthalen-1-yl]ethyl acetate (413578-15-1)

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%

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 3-Aminobenzamide (3544-24-9) → N-(3-carbamoylphenyl)-5-nitro-1-benzofuran-2-carboxamide

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

ethyl 5-amino-1H-indole-2-carboxylate (71086-99-2) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → ethyl 5-[(5-nitro-1H-benzofuran-2-ylcarbonyl)amino]-1H-indole-2-carboxylate (266348-99-6)

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + benzyl chloroformate (501-53-1) → benzyl 5-nitrobenzofuran-2-ylcarbamate (1277175-54-8)

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + (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

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%

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → 2-fluoro-5-nitrobenzofuran

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

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + 2-(2-amino-4-benzyloxyphenyl)ethyl chloride (413577-26-1) → 2-(4-benzyloxy-2-(5-nitrobenzofuran-2-carboxamido)phenyl)ethyl chloride (413577-33-0)

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;

5-nitrobenzofuran-2-carboxylic acid (10242-12-3) + C9H14N4O3 → C18H17N5O7

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

methanol (67-56-1) + 5-nitrobenzofuran-2-carboxylic acid (10242-12-3) → 5-nitrobenzofuran-2-carboxylic Acid Methyl Ester (104862-11-5)

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;

Upstream product

• 6965-69-1 2-(2-formyl-4-nitrophenoxy)acetic acid 
• 50396-49-1 3-(2-hydroxy-5-nitrophenyl)acrylic acid 
• 2725-81-7 6-nitrocoumarin 
• 90-02-8 salicylaldehyde 
• 6280-80-4 2-Formylphenoxyacetic acid 
• 69604-00-8 ethyl 5-nitrobenzo[d]furan-2-carboxylate 
• 51336-43-7 2-formyl-4-nitrophenoxyacetic acid ethyl ester 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 685-87-0 Diethyl 2-bromomalonate 
• 97-51-8 5-Nitrosalicylaldehyde 
• 5415-73-6 3-bromo-6-nitro-2H-chromen-2-one 
• 3199-61-9 ethyl coumarilate 
• 939-18-4 3-bromo-2H-chromen-2-one 

Downstream Products

• 90322-48-8 (5-nitro-1-benzofuran-2-yl)methanol 
• 267644-49-5 5-nitro-1-benzofuran-2-carboxamide 
• 183288-46-2 5-(1-piperazinyl)benzofuran-2-carboxamide 
• 163521-12-8 vilazodone 
• 69604-00-8 ethyl 5-nitrobenzo[d]furan-2-carboxylate 
• 174775-48-5 ethyl 5-amino-1-benzofuran-2-carboxylate 
• 163521-20-8 5-(piperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester 

Relevant articles and documents

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[...] intermediate synthetic method (by machine translation)

The invention relates to a [...] intermediate synthesis method, in order to 6 - nitro coumarin as the starting the raw materials, through ring-opening, the ring in the molecule, esterification, reduction, paipai qin link other steps, to obtain key [...] middle style I compound 5 - (1 - piperazinyl) - 2 - benzofuran - 2 - carboxylic acid ethyl ester. The invention synthetic route is simple, the target product yield is relatively high, and is suitable for industrial scale production. (by machine translation)

1-(CYCLOALKYL-CARBONYL)PROLINE DERIVATIVE

A compound represented by formula (1) (in the formula: ring-D represents a three- to eight-membered hydrocarbon ring; Ra represents an optionally substituted amino C1-6 alkyl group or the like; Rb1 and Rb2 each independently represent a hydrogen atom, a halogen atom, or the like; Rc represents an optionally substituted C6-10 aryl group or the like; Rd represents a hydrogen atom or the like; and ring-Q represents a (hetero)aryl group or the like which may be substituted with a carboxyl group or the like) or a pharmaceutically acceptable salt thereof exhibits an excellent FXIa inhibitory activity, and is useful as a therapeutic agent against thrombosis or the like.