Product Name

  • Name

    4-Nitrophthalic acid

  • EINECS 210-215-3
  • CAS No. 610-27-5
  • Article Data60
  • CAS DataBase
  • Density 1.671 g/cm3
  • Solubility 880 g/l at 20 °C
  • Melting Point 159-161 °C(lit.)
  • Formula C8H5NO6
  • Boiling Point 459.5 °C at 760 mmHg
  • Molecular Weight 211.131
  • Flash Point 207.6 °C
  • Transport Information
  • Appearance Light-beige solid
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 610-27-5 (4-Nitrophthalic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 4-nitrobenzene-1,2-dicarboxylic acid;4-nitrobenzene-1,2-dicarboxylate;5-Nitrophthalic acid;Phthalic acid, 4-nitro-;1,2-Benzenedicarboxylic acid, 4-nitro-;4-Nitrophthalic acid (4-NPA);p-Nitro Phthalic Acid;
  • PSA 120.42000
  • LogP 1.51440

Synthetic route

4-Nitrophthalonitrile
31643-49-9

4-Nitrophthalonitrile

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.45h; Green chemistry;95%
phthalic anhydride
85-44-9

phthalic anhydride

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

3-nitrophthalic acid
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℃;
4-nitro-o-xylene
99-51-4

4-nitro-o-xylene

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate In water at 20℃; for 12h; Sonication;50%
With potassium permanganate In water for 12h; Sonication;50%
With nitric acid at 170 - 180℃; im geschlossenen Rohr;
Multi-step reaction with 2 steps
1: NBS, (PhCO)2O2 / CCl4
2: KMnO4, aq. K2CO3
View Scheme
phthalic anhydride
85-44-9

phthalic anhydride

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid
Stage #1: phthalic anhydride With sulfuric acid for 0.166667h;
Stage #2: With nitric acid at 70℃; for 1h; Temperature;
5-nitroisoindoline
46053-72-9

5-nitroisoindoline

A

4-nitrophthalimide
89-40-7

4-nitrophthalimide

B

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid
5-nitro-3H-isobenzofuran-1-one
67081-02-1

5-nitro-3H-isobenzofuran-1-one

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid at 140℃; im geschlossenen Rohr;
With potassium permanganate; water
6-nitrotetralin
19353-86-7

6-nitrotetralin

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With permanganate(VII) ion anschliessend behandeln in Schwefelsaeure;
2-(carboxymethyl)-5-nitrobenzoic acid
3898-66-6

2-(carboxymethyl)-5-nitrobenzoic acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid
2,4,7-trinitro-1-naphthalenol
38319-14-1

2,4,7-trinitro-1-naphthalenol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid
6-nitroindan-1-one
24623-24-3

6-nitroindan-1-one

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With alkaline permanganate
2-cyano-5-nitrotoluene
89001-53-6

2-cyano-5-nitrotoluene

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With sodium hydroxide; permanganate(VII) ion
2-formyl-5-nitrobenzoic acid
7464-91-7

2-formyl-5-nitrobenzoic acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate
3-hydroxy-7-nitro-naphthalene-1-sulfonic acid
68516-57-4

3-hydroxy-7-nitro-naphthalene-1-sulfonic acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With water; permanganate(VII) ion
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

3-nitrophthalic acid
603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid
With nitric acid at 30℃;
With sulfuric acid; nitric acid
1,2-bis-bromomethyl-4-nitro-benzene
6425-66-7

1,2-bis-bromomethyl-4-nitro-benzene

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With potassium permanganate; potassium carbonate
3,4-bis(trifluoromethyl)nitrobenzene
1978-20-7

3,4-bis(trifluoromethyl)nitrobenzene

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid at 195 - 205℃;
4-nitrophthalimide
89-40-7

4-nitrophthalimide

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With potassium hydroxide; nitric acid 1.) reflux, 10 min, 2.) reflux, 3 min; Yield given. Multistep reaction;
1,1,2,2-Tetrachlor-4-nitro-benzocyclobuten
64726-12-1

1,1,2,2-Tetrachlor-4-nitro-benzocyclobuten

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide
6-nitrophthalide
610-93-5

6-nitrophthalide

nitric acid
7697-37-2

nitric acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
at 140℃;
phthalic anhydride
85-44-9

phthalic anhydride

HNO3+H2SO4

HNO3+H2SO4

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

3-nitrophthalic acid
603-11-2

3-nitrophthalic acid

hydrogenchloride
7647-01-0

hydrogenchloride

6-nitro-2,3-dihydrophthalazine-1,4-dione
3682-19-7

6-nitro-2,3-dihydrophthalazine-1,4-dione

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

hydrazine
302-01-2

hydrazine

Conditions
ConditionsYield
at 150℃; im Rohr;
5-nitroisoindoline
46053-72-9

5-nitroisoindoline

diluted Cr2O3-H2SO4

diluted Cr2O3-H2SO4

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

<4-nitro-phthalic acid >-imide

<4-nitro-phthalic acid >-imide

nitric acid
7697-37-2

nitric acid

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

3-nitrophthalic acid
603-11-2

3-nitrophthalic acid

Conditions
ConditionsYield
at 30℃; Product distribution;
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

HNO3+H2SO4

HNO3+H2SO4

A

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

B

3-nitrophthalic acid
603-11-2

3-nitrophthalic acid

4-nitro-homophthalic acid

4-nitro-homophthalic acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid
5-nitro-indanone-(2)

5-nitro-indanone-(2)

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With nitric acid
<4-nitro-phthalic acid >-imide

<4-nitro-phthalic acid >-imide

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With sodium hydroxide; water versetzen mit Salpetersaeure;
5-nitroindane
7436-07-9

5-nitroindane

alkaline permanganate solution

alkaline permanganate solution

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-nitro-o-xylene
99-51-4

4-nitro-o-xylene

nitric acid
7697-37-2

nitric acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
at 170 - 180℃;
methanesulfonic acid
75-75-2

methanesulfonic acid

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-amino-phthalic acid dimethyl ester
51832-31-6

4-amino-phthalic acid dimethyl ester

Conditions
ConditionsYield
Stage #1: methanesulfonic acid; 4-nitrophthalic acid In methanol Reflux;
Stage #2: With palladium on activated charcoal; hydrogen In methanol; water at 37℃; for 9h;
100%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

(4-nitro-1,2-phenylene)dimethanol
22162-19-2

(4-nitro-1,2-phenylene)dimethanol

Conditions
ConditionsYield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane99%
With borane-THF In tetrahydrofuran at 0 - 20℃;98%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 0.001875h; Inert atmosphere;98%
ethanol
64-17-5

ethanol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-nitrophthalic acid diethyl ester
2050-19-3

4-nitrophthalic acid diethyl ester

Conditions
ConditionsYield
With sulfuric acid In ethanol at 100℃; for 24h;98%
With sulfuric acid for 15h; Dean-Stark; Reflux;97%
With hydrogenchloride at 80℃; for 72h; Esterification;78%
propan-1-ol
71-23-8

propan-1-ol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-nitrophthalic acid di-n-propyl ester
53577-25-6

4-nitrophthalic acid di-n-propyl ester

Conditions
ConditionsYield
With sulfuric acid for 15h; Dean-Stark; Reflux;97%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-aminophthalic acid
5434-21-9

4-aminophthalic acid

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In ethanol at 20℃; for 3h;96%
With hydrogen; 5%-palladium/activated carbon In ethanol at 20℃; for 3h;96%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h;93%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-(5-nitro-1,3-dioxoisoindolin-2-yl)benzoic acid
148149-88-6

4-(5-nitro-1,3-dioxoisoindolin-2-yl)benzoic acid

Conditions
ConditionsYield
In acetonitrile at 180℃; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;96%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

butan-1-ol
71-36-3

butan-1-ol

4-nitrophthalic acid di-n-butyl ester
3164-72-5

4-nitrophthalic acid di-n-butyl ester

Conditions
ConditionsYield
With sulfuric acid for 15h; Dean-Stark; Reflux;96%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-nitrophthalic anhydride
5466-84-2

4-nitrophthalic anhydride

Conditions
ConditionsYield
With acetic anhydride93%
With acetic anhydride 1) 60 deg C, 1 h; 2) reflux, 10 min;90%
With acetic anhydride for 0.333333h; Heating;88%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-nitrophthalic acid chloride
24564-72-5

4-nitrophthalic acid chloride

Conditions
ConditionsYield
With thionyl chloride at 78℃; for 3.25h;93%
With phosphorus pentachloride
With thionyl chloride
With thionyl chloride
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

N-(hydroxycarbonylmethyl)pyridinium bromide
45811-13-0

N-(hydroxycarbonylmethyl)pyridinium bromide

N-(5-nitro-1H-indene-1,3(2H)-dion-2-yl)pyridinium betaine

N-(5-nitro-1H-indene-1,3(2H)-dion-2-yl)pyridinium betaine

Conditions
ConditionsYield
With acetic anhydride; triethylamine In acetonitrile Condensation; Heating;92%
2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

bis(2-ethylhexyl) 4-nitrophthalate
59986-42-4

bis(2-ethylhexyl) 4-nitrophthalate

Conditions
ConditionsYield
With titanium(IV) isopropylate at 150℃; for 4h;91.1%
With titanium(IV) isopropylate at 150℃; for 4h;86%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-amino-N-carboxymethylpyridinium bromide

4-amino-N-carboxymethylpyridinium bromide

N-(5-nitro-1H-indene-1,3(2H)-dion-2-yl)-4'-(4-nitrophthalimido)pyridinium betaine

N-(5-nitro-1H-indene-1,3(2H)-dion-2-yl)-4'-(4-nitrophthalimido)pyridinium betaine

Conditions
ConditionsYield
With acetic anhydride; triethylamine In acetic acid; acetonitrile Condensation; acylation; Heating;88%
copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

copper(II) 2,9,16,23-tetranitrohophthalocyanine
118-20-7

copper(II) 2,9,16,23-tetranitrohophthalocyanine

Conditions
ConditionsYield
With urea In neat (no solvent) heating a mixture of copper sulphate pentahydrate, 4-nitrophthalic aicd, a catalytic quantity of NH4Cl/(NH4)2MoO4 and an excess of urea at 185°C for 5 h; elem. anal.;88%
1,3-diazido 2-propanol
57011-48-0

1,3-diazido 2-propanol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

bis(1,3-diazidopropan-2-yl) 4-nitrophthalate

bis(1,3-diazidopropan-2-yl) 4-nitrophthalate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;88%
3,5-dimethyl-1H-pyrazole
67-51-6

3,5-dimethyl-1H-pyrazole

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

C5H8N2*C8H5NO6

C5H8N2*C8H5NO6

Conditions
ConditionsYield
In methanol; ethanol87.87%
piperidine
110-89-4

piperidine

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

C5H11N*C8H5NO6

C5H11N*C8H5NO6

Conditions
ConditionsYield
In methanol for 0.25h;87.75%
1H-imidazole
288-32-4

1H-imidazole

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

C3H4N2*C8H5NO6

C3H4N2*C8H5NO6

Conditions
ConditionsYield
In methanol; ethanol85.96%
ethanol
64-17-5

ethanol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

water
7732-18-5

water

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

potassium hydroxide

potassium hydroxide

trans-1,2-bis(4-pyridyl)ethylene
1135-32-6

trans-1,2-bis(4-pyridyl)ethylene

2C8H3NO6(2-)*2C12H10N2*2HO(1-)*3Zn(2+)*H2O*C2H6O

2C8H3NO6(2-)*2C12H10N2*2HO(1-)*3Zn(2+)*H2O*C2H6O

Conditions
ConditionsYield
at 120℃; for 96h; Autoclave;85%
2-(1H-imidazol-1-yl)-1-phenylethanone
24155-34-8

2-(1H-imidazol-1-yl)-1-phenylethanone

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

2-(imidazolium-1-yl)-1-phenylethanone 4-nitrohydrogenphthalate

2-(imidazolium-1-yl)-1-phenylethanone 4-nitrohydrogenphthalate

Conditions
ConditionsYield
In methanol; ethanol83.05%
2-methylquinoline
91-63-4

2-methylquinoline

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

C10H9N*C8H5NO6

C10H9N*C8H5NO6

Conditions
ConditionsYield
In methanol81.85%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

(2,6‑dimethylaniline):(4‑nitrophthalic acid)

(2,6‑dimethylaniline):(4‑nitrophthalic acid)

Conditions
ConditionsYield
In methanol81.25%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

bis(4-(1H-imidazol-1-yl)phenyl)methanone

bis(4-(1H-imidazol-1-yl)phenyl)methanone

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

{[Zn(npa)(L1)]*2H2O}n

{[Zn(npa)(L1)]*2H2O}n

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 95℃; for 336h;81%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

8-azidooctan-1-ol
57395-46-7

8-azidooctan-1-ol

bis(8-azidooctyl)4-nitrophthalate

bis(8-azidooctyl)4-nitrophthalate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;79%
8-quinolinol
148-24-3

8-quinolinol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

C9H7NO*C8H5NO6

C9H7NO*C8H5NO6

Conditions
ConditionsYield
In methanol; ethanol at 20℃;78.58%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

nicotinamide
98-92-0

nicotinamide

C6H6N2O*C8H5NO6

C6H6N2O*C8H5NO6

Conditions
ConditionsYield
In methanol78.02%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

isonicotinamide
1453-82-3

isonicotinamide

C6H6N2O*C8H5NO6

C6H6N2O*C8H5NO6

Conditions
ConditionsYield
In methanol78.02%
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

C9H11NO*C8H5NO6

C9H11NO*C8H5NO6

Conditions
ConditionsYield
In methanol at 20℃; for 480h;77.71%
methanol
67-56-1

methanol

4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

dimethyl 4-nitrophthalate
610-22-0

dimethyl 4-nitrophthalate

Conditions
ConditionsYield
With sulfuric acid for 18.1667h; Reflux;76%
With hydrogenchloride
With sulfuric acid

4-Nitrophthalic acid Chemical Properties

Molecule structure of 4-Nitrophthalic acid (CAS NO.610-27-5):

IUPAC Name: 4-Nitrophthalic acid 
Molecular Weight: 211.1284 g/mol
Molecular Formula: C8H5NO6 
Density: 1.671 g/cm
Melting Point: 159-161 °C(lit.)
Boiling Point: 459.5 °C at 760 mmHg 
Flash Point: 207.6 °C
Index of Refraction: 1.66
Molar Refractivity: 46.65 cm3
Molar Volume: 126.3 cm3
Polarizability: 18.49×10-24 cm3
Surface Tension: 88 dyne/cm 
Enthalpy of Vaporization: 75.86 kJ/mol
Vapour Pressure: 3.09E-09 mmHg at 25 °C
XLogP3: 0.9
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)5-2-1-4(9(14)15)3-6(5)8(12)13/h1-3H,(H,10,11)(H,12,13)
InChIKey: SLBQXWXKPNIVSQ-UHFFFAOYSA-N
EINECS: 210-215-3
Product Categories: Phthalic Acids, Esters and Derivatives; Organic acids; Aromatics Compounds; Aromatics; C8; Carbonyl Compounds; Carboxylic Acids

4-Nitrophthalic acid Uses

 4-Nitrophthalic acid (CAS NO.610-27-5) is used as intermediates in organic synthesis.

4-Nitrophthalic acid Production

Adding 4-nitrophenyl-dicarboximide to sodium hydroxide solution, heated to boiling, adding concentrated nitric acid to acidic solution on litmus, the solution boiled 3min, cool to room temperature, extracted with ether. The extract was dried by sodium sulfide, except ether, get 4-nitro-phthalic acid, the yield of 96% -99%.

4-Nitrophthalic acid Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
HS Code: 29173980

4-Nitrophthalic acid Specification

 4-Nitrophthalic acid (CAS NO.610-27-5) is also named as 5-Nitrophthalic acid ; AI3-08820 ; NSC 5395 ; Phthalic acid, 4-nitro- ; 1,2-Benzenedicarboxylic acid, 4-nitro- . 4-Nitrophthalic acid (CAS NO.610-27-5) is light-beige solid.

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