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603-11-2

Basic Information
CAS No.: 603-11-2
Name: 3-Nitrophthalic acid
Molecular Structure:
Molecular Structure of 603-11-2 (3-Nitrophthalic acid)
Formula: C8H5NO6
Molecular Weight: 211.13
Synonyms: Phthalic acid, 3-nitro- (6CI,7CI,8CI);3-Nitro-1,2-benzenedicarboxylic acid;
EINECS: 210-030-8
Density: 1.671 g/cm3
Melting Point: 210 °C (dec.)(lit.)
Boiling Point: 441.3 °C at 760 mmHg
Flash Point: 199.4 °C
Solubility: 20 g/L (25 °C) in water
Appearance: pale yellow crystals
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-41
Safety: 26-36/39-37/39-36
Transport Information:
PSA: 120.42000
LogP: 1.51440
Synthetic route
13365-26-9

dimethyl 3-nitrophthalate

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Reflux;93%
85-44-9

phthalic anhydride

A

610-27-5

4-nitrophthalic acid

B

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 80 - 110℃;A 80%
B n/a
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid at 25℃;

ammonium salt of 3-nitrophthalic acid

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With hydrogenchloride In water pH=2;56%
85-44-9

phthalic anhydride

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With boron trifluoride; nitric acid; acetic acid
durch Nitrierung;
durch Nitrieren;
42760-46-3

7-nitro-3H-isobenzofuran-1-one

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid im geschlossenen Rohr;
91-20-3

naphthalene

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid
65399-18-0

4-nitrophthalide

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid im geschlossenen Rohr;
86-57-7

1-Nitronaphthalene

A

65399-18-0

4-nitrophthalide

B

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
86-57-7

1-Nitronaphthalene

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate
With chromium(VI) oxide; acetic acid
83-41-0

2,3-dimethylnitrobenzene

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid at 170 - 180℃; im geschlossenen Rohr;
Stage #1: 2,3-dimethylnitrobenzene With oxygen; nitric acid at 145 - 150℃; under 26252.6 - 30003 Torr; for 8h;
Stage #2: With oxygen; nitric acid at 130 - 140℃; under 26252.6 - 30003 Torr; for 30h; Pressure; Temperature;
25.2 g
91974-35-5

ethyl-(4,5-dinitro-[1]naphthyl)-ether

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
bei der Oxydation;
161851-52-1

6-nitrosalicylaldehyde

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate
112534-15-3

(2-carboxy-6-nitro-phenyl)-glyoxylic acid

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With permanganate(VII) ion
112534-27-7

(2-carboxy-3-nitro-phenyl)-glyoxylic acid

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With permanganate(VII) ion
605-71-0

1,5-dinitronaphthalene

A

99-34-3

3,5-dinitrobenzoic acid

B

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid at 150℃; im geschlossenen Rohr;
88-99-3

benzene-1,2-dicarboxylic acid

A

610-27-5

4-nitrophthalic acid

B

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid
With nitric acid at 30℃;
With sulfuric acid; nitric acid
88-99-3

benzene-1,2-dicarboxylic acid

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
durch Nitrierung;
89939-50-4

3-Nitro-5-amino-phthalsaeure

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
(i) NaNO2, aq. HCl, (ii) aq. EtOH; Multistep reaction;
89939-48-0

3-Nitro-4-amino-phthalsaeure

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
(i) NaNO2, aq. HCl, (ii) aq. EtOH; Multistep reaction;
83-41-0

2,3-dimethylnitrobenzene

A

1975-50-4

2-methyl-3-nitrobenzic acid

B

13506-76-8

2-methyl-6-nitrobenzoic acid

C

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate; cetyltrimethylammonim bromide In water at 75℃; for 4h; Product distribution; effect of the amount of KMnO4; further catalysts;
With potassium permanganate; cetyltrimethylammonim bromide In water at 75℃; for 4h; Yield given. Yields of byproduct given;
With potassium permanganate; tetrabutylammomium bromide In water
With oxygen; nitric acid at 130 - 140℃; under 16501.7 - 18751.9 Torr; for 7h; Temperature; Pressure;
4685-53-4

6,8-Dimethyl-1-nitro-7H-benzocyclohepten-7-on

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate
1978-06-9

1,2-Bis(trifluoromethyl)-3-nitrobenzene

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid at 150℃;
64726-10-9

1,1,2,2-Tetrafluor-3-nitro-benzocyclobuten

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide
607-32-9

5-nitroisoquinoline

7697-37-2

nitric acid

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
at 180 - 200℃;
65399-18-0

4-nitrophthalide

7697-37-2

nitric acid

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
im geschlossenen Rohr;
65399-18-0

4-nitrophthalide

64-19-7

acetic acid

CrO3

CrO3

603-11-2

3-nitrophthalic acid

607-32-9

5-nitroisoquinoline

permanganate

permanganate

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
at 60℃; in neutraler Loesung;
85-44-9

phthalic anhydride

HNO3+H2SO4

HNO3+H2SO4

A

610-27-5

4-nitrophthalic acid

B

603-11-2

3-nitrophthalic acid

88-99-3

benzene-1,2-dicarboxylic acid

HNO3+H2SO4

HNO3+H2SO4

603-11-2

3-nitrophthalic acid

7697-37-2

nitric acid

88-99-3

benzene-1,2-dicarboxylic acid

A

610-27-5

4-nitrophthalic acid

B

603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
at 30℃; Product distribution;
67-56-1

methanol

603-11-2

3-nitrophthalic acid

13365-26-9

dimethyl 3-nitrophthalate

Conditions
ConditionsYield
Stage #1: 3-nitrophthalic acid With thionyl chloride Heating / reflux;
Stage #2: methanol Heating / reflux;
100%
With sulfuric acid
With sulfuric acid Reflux;
603-11-2

3-nitrophthalic acid

13365-26-9

dimethyl 3-nitrophthalate

Conditions
ConditionsYield
In diethyl ether100%
603-11-2

3-nitrophthalic acid

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In cyclohexane at 5 - 10℃; for 3.83333h; Time; Reagent/catalyst; Solvent; Temperature; Vilsmeier Reaction; Reflux;98.9%
With acetic anhydride for 2h; Reflux;95%
With acetic anhydride for 2h; Reflux;95.8%
67-56-1

methanol

603-11-2

3-nitrophthalic acid

21606-04-2

methyl 2-carboxy-3-nitrobenzoate

Conditions
ConditionsYield
With thionyl chloride at 5℃; for 20 - 25h; Heating / reflux;98%
With thionyl chloride at -10 - 10℃; for 10h; Reflux;98.4%
With hydrogenchloride In methanol Heating;77%
603-11-2

3-nitrophthalic acid

105903-25-1

methyl 4-amino-3-methoxy-2-naphthoate

1264626-10-9

3-methoxy-4-(4-nitro-1,3-dioxo-1,3-dihydroisoindol-2-yl)naphthalene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
at 140℃; for 0.5h;98%
603-11-2

3-nitrophthalic acid

603-62-3

4-nitro-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With acetic acid; urea at 117℃; for 3h;98%
With acetic acid; urea for 4h; Reflux;87%
With urea In acetic acid at 140℃; for 4h;82%
With ammonium carbonate at 220 - 230℃; for 1h;
With urea In N,N-dimethyl-formamide at 110℃; for 5h;
603-11-2

3-nitrophthalic acid

5434-20-8

3-aminophthalic acid

Conditions
ConditionsYield
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃;97%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;97%
With hydrogen; palladium-containing anion exchanger AB-17-8-Pd In ethanol at 20 - 40℃; under 750.06 Torr; Kinetics; Product distribution; Further Variations:; Catalysts;97%
603-11-2

3-nitrophthalic acid

619-45-4

4-methoxycarbonyl aniline

4-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-benzoic acid methyl ester

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide cyclocondensation; Heating;96%
96-31-1

N,N'-Dimethylurea

603-11-2

3-nitrophthalic acid

Ethyl S-(acetylamino)-1,2,3,4-tetrahydro-2-methyl-7-nitro-8-isoquinolinepropanoate

Conditions
ConditionsYield
In ethanol96%
71-23-8

propan-1-ol

603-11-2

3-nitrophthalic acid

13325-35-4

3-nitrophthalic acid di-n-propyl ester

Conditions
ConditionsYield
With sulfuric acid for 15h; Dean-Stark; Reflux;96%
603-11-2

3-nitrophthalic acid

74-88-4

methyl iodide

13365-26-9

dimethyl 3-nitrophthalate

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 60℃; for 4h;95%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 60℃; for 4h;95%
With sodium hydrogencarbonate In N,N-dimethyl-formamide Inert atmosphere; Heating;91%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 16h;
603-11-2

3-nitrophthalic acid

71-36-3

butan-1-ol

13325-37-6

3-nitrophthalic acid di-n-butyl ester

Conditions
ConditionsYield
With sulfuric acid for 15h; Dean-Stark; Reflux;95%
603-11-2

3-nitrophthalic acid

149-73-5

trimethyl orthoformate

21606-04-2

methyl 2-carboxy-3-nitrobenzoate

Conditions
ConditionsYield
With sulfuric acid In methanol at 59 - 65℃; for 15 - 20h; Heating / reflux; Industry scale;94.7%
With sulfuric acid In methanol
603-11-2

3-nitrophthalic acid

106860-70-2

3-Nitroso-phthalic acid

Conditions
ConditionsYield
With hydrogenchloride; disodium hydrogenphosphate; sodium dihydrogenphosphate In water porous cathode and anode;93%
In water electrolysis in phosphate buffer;95 % Spectr.
603-11-2

3-nitrophthalic acid

121-92-6

3-nitrobenzoic acid

Conditions
ConditionsYield
With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 16h; regioselective reaction;92%
603-11-2

3-nitrophthalic acid

3-aminophthalic acid hydrochloride

Conditions
ConditionsYield
Stage #1: 3-nitrophthalic acid With 10 wt% Pd(OH)2 on carbon; ammonium formate In methanol at 65℃;
Stage #2: With hydrogenchloride In methanol; water at 40℃; for 1h; Temperature; Solvent;
90.6%
603-11-2

3-nitrophthalic acid

106-49-0

p-toluidine

53555-10-5

4-nitro-2-p-tolyl-isoindole-1,3-dione

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide cyclocondensation; Heating;90%
603-11-2

3-nitrophthalic acid

56-40-6

glycine

15784-35-7

2-(4-nitro-1,3-dioxoisoindolin-2-yl)acetic acid

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide at 165 - 170℃; for 1.5h; cyclocondensation;90%
With propionic acid at 170 - 180℃;84%
603-11-2

3-nitrophthalic acid

6946-22-1

3-aminophthalic acid hydrochloride

Conditions
ConditionsYield
With sodium hydroxide; acetic acid; PtO2 In water; acetone90%
With sodium hydroxide; acetic acid; PtO2 In water; acetone90%
Stage #1: 3-nitrophthalic acid With palladium 10% on activated carbon; hydrogen In ethanol at 20 - 25℃; under 1500.15 Torr; for 3h; Autoclave;
Stage #2: With hydrogenchloride In acetone at 10℃; Solvent; Pressure;
65 g
Stage #1: 3-nitrophthalic acid With palladium on activated charcoal; hydrogen at 55 - 65℃; under 5250.53 - 6750.68 Torr; for 12h; Large scale;
Stage #2: With hydrogenchloride In water at -5 - 5℃; for 1h; Large scale;
603-11-2

3-nitrophthalic acid

75-03-6

ethyl iodide

62351-79-5

3-nitrobenzene-1,2-dicarboxylate ester

Conditions
ConditionsYield
Stage #1: 3-nitrophthalic acid With sulfuric acid In ethanol; water at 80℃;
Stage #2: ethyl iodide With potassium carbonate In N,N-dimethyl-formamide
90%
Stage #1: 3-nitrophthalic acid With sulfuric acid In ethanol for 6h; Reflux;
Stage #2: ethyl iodide With potassium carbonate In N,N-dimethyl-formamide at 20℃;
89.9%
603-11-2

3-nitrophthalic acid

24666-56-6

rac-α-aminoglutarimide hydrochloride

Conditions
ConditionsYield
With sodium acetate; acetic acid at 105 - 115℃; Large scale;90%
With sodium acetate; acetic acid In water at 116 - 118℃; for 16h;86.2%
With 1,1'-carbonyldiimidazole In acetonitrile at 20 - 80℃; Inert atmosphere;28.2 g
603-11-2

3-nitrophthalic acid

62-53-3

aniline

19065-85-1

3-nitro-N-phenylphthalimide

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide cyclocondensation; Heating;85%
603-11-2

3-nitrophthalic acid

26429-41-4

1,2-dibromo-3-nitrobenzene

Conditions
ConditionsYield
With Bromotrichloromethane; trichloroisocyanuric acid; bromine at 10 - 120℃; for 60h; Photolysis;85%
603-11-2

3-nitrophthalic acid

150-13-0

4-amino-benzoic acid

C7H7NO2*C8H5NO6

Conditions
ConditionsYield
In methanol for 0.25h;83.27%
603-11-2

3-nitrophthalic acid

100-10-7

4-dimethylamino-benzaldehyde

C9H11NO*C8H5NO6

Conditions
ConditionsYield
In methanol at 20℃; for 336h;83.26%
603-11-2

3-nitrophthalic acid

108-24-7

acetic anhydride

6296-53-3

3-acetylaminophthalic anhydride

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen at 80 - 115℃; under 7500.75 Torr; Temperature; Autoclave;83%
603-11-2

3-nitrophthalic acid

C47H65N15O9S

C54H66N16O10S

Conditions
ConditionsYield
In ethanol at 4 - 20℃; pH=Ca. 9;82%
603-11-2

3-nitrophthalic acid

150-13-0

4-amino-benzoic acid

71494-65-0

3-nitro-N-(p-carboxyphenyl)phthalimide

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide cyclocondensation; Heating;81%
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    SYNONYMS 3-Nitrobenzene-1,2-dicarboxylic acid;3-Nitro-1,2-benzenedicarboxylic acid DESCRIPTION White to off-white crysta… Appearance:White to off-white crystalline powder Package:25KGS/drum Application:Intermediates for organic synthesis

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    3-nitrophthalate

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    3-Nitrophthalic acid CAS:603-11-2

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    Product Name 3-Nitrophthalic acid Synonyms 3-nitro-2-benzenedicarboxylicacid CAS Registry Number 603-11-2 Molecular Structure

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Chemistry

Molecule structure of 3-Nitrophthalic acid (CAS NO.603-11-2):

IUPAC Name: 3-Nitrophthalic acid 
Molecular Weight: 211.1284 g/mol
Molecular Formula: C8H5NO6 
Density: 1.671 g/cm3 
Melting Point: 210 °C (dec.)(lit.)
Boiling Point: 441.3 °C at 760 mmHg 
Flash Point: 199.4 °C
Index of Refraction: 1.66
Molar Refractivity: 46.65 cm3
Molar Volume: 126.3 cm3
Surface Tension: 88 dyne/cm
Enthalpy of Vaporization: 73.63 kJ/mol
Vapour Pressure: 1.45E-08 mmHg at 25 °C 
Water Solubility: 20 g/L (25 °C)
XLogP3: 0.7
H-Bond Donor: 2
H-Bond Acceptor: 6
Rotatable Bond Count: 2
Exact Mass: 211.011687
MonoIsotopic Mass: 211.011687
Topological Polar Surface Area: 118
Heavy Atom Count: 15
Canonical SMILES: C1=CC(=C(C(=C1)[N+](=O)[O-])C(=O)O)C(=O)O
InChI: InChI=1S/C8H5NO6/c10-7(11)4-2-1-3-5(9(14)15)6(4)8(12)13/h1-3H,(H,10,11)(H,12,13)
InChIKey: KFIRODWJCYBBHY-UHFFFAOYSA-N
EINECS: 210-030-8
Product Categories: Phthalic Acids, Esters and Derivatives; Organics; Organic acids; Dyes intermediates; C8; Carbonyl Compounds; Carboxylic Acids

Uses

 3-Nitrophthalic acid is mainly used as sensitive materials and pharmaceutical intermediates. It is available for the preparation of medicines, dyes, crop protection agents in organic synthesis.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38-41 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R41:Risk of serious damage to the eyes.
Safety Statements: 26-36/39-37/39-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S39:Wear eye / face protection.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant
HS Code: 29173980
A preparative hazard. When heated to decomposition it emits toxic fumes of NOx.

Specification

 3-Nitrophthalic acid (CAS NO.603-11-2) is also named as AI3-02074 ; NSC 3120 ; 1,2-Benzenedicarboxylic acid, 3-nitro- ; Phthalic acid, 3-nitro- (8CI) . 3-Nitrophthalic acid (CAS NO.603-11-2) is pale yellow crystals. It is soluble in water, methanol, ethanol, slightly soluble in ether, insoluble in chloroform, carbon tetrachloride, carbon disulfide, benzene. 3-Nitrophthalic acid is stable and incompatible with strong oxidizing agents.

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