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10242-12-3

Basic Information
CAS No.: 10242-12-3
Name: 5-Nitrobenzofuran-2-carboxylic acid
Article Data: 15
Molecular Structure:
Molecular Structure of 10242-12-3 (5-Nitrobenzofuran-2-carboxylic acid)
Formula: C9H5NO5
Molecular Weight: 207.142
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;
Density: 1.584 g/cm3
Melting Point: 274 °C
Boiling Point: 414 °C at 760 mmHg
Flash Point: 204.2 °C
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With nitric acid; tin(IV) chloride In dichloromethane at 0℃; for 2h;A 16%
B 16%
C 39%
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
ConditionsYield
With nitric acid; tin(IV) chloride In dichloromethane at 0℃; for 2h;A 5%
B 33%
C 33%
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
ConditionsYield
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
5415-73-6

3-bromo-6-nitro-2H-chromen-2-one

10242-12-3

5-nitrobenzofuran-2-carboxylic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium carbonate; butanone
2-formyl-<4-nitro-phenoxy>-acetic acid

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

10242-12-3

5-nitrobenzofuran-2-carboxylic acid

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