Product Name

  • Name

    4-Nitrophthalimide

  • EINECS 201-905-5
  • CAS No. 89-40-7
  • Article Data59
  • CAS DataBase
  • Density 1.609 g/cm3
  • Solubility <0.01 g/100 mL at 18 °C in water
  • Melting Point 206 °C
  • Formula C8H4N2O4
  • Boiling Point 328.09°C (rough estimate)
  • Molecular Weight 192.131
  • Flash Point
  • Transport Information
  • Appearance slight yellow powder
  • Safety 37/39-26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 89-40-7 (4-Nitrophthalimide)
  • Hazard Symbols IrritantXi
  • Synonyms Phthalimide, 4-nitro- (6CI,7CI,8CI);
  • PSA 91.99000
  • LogP 1.33040

Synthetic route

4-nitrophthalic anhydride
5466-84-2

4-nitrophthalic anhydride

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With formamide In neat (no solvent) for 0.25h; Reagent/catalyst; Milling; Heating; Green chemistry;95%
With formamide for 0.0333333h; microwave irradiation;90%
With formamide In 1-methyl-pyrrolidin-2-one at 170 - 180℃;90.15%
With formamide for 0.05h; microwave irradiation;64%
With ammonia in Schmelze;
phthalimide
136918-14-4

phthalimide

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 10 - 25℃; for 12h;94%
With sulfuric acid; nitric acid87%
With sulfuric acid; nitric acid at 0℃; for 5h;85%
5-nitro-2,3-dihydroinden-1-one
22246-24-8

5-nitro-2,3-dihydroinden-1-one

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With manganese(IV) oxide; ammonium hydroxide; oxygen; chlorobenzene In N,N-dimethyl-formamide at 100℃; under 15001.5 Torr; for 24h; Autoclave; Green chemistry;83%
ethyl 2-chloro-4-nitrobenzoate
73097-02-6

ethyl 2-chloro-4-nitrobenzoate

copper(I) cyanide
544-92-3

copper(I) cyanide

A

ethyl 2-cyano-4-nitro-benzoate

ethyl 2-cyano-4-nitro-benzoate

B

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 135 - 140℃; for 12h;A 68%
B 8.6 g
...Expand
2-hydroxy-6-nitro-1H-isoindole-1,3-dione
105969-98-0

2-hydroxy-6-nitro-1H-isoindole-1,3-dione

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With potassium acetate; bis(pinacol)diborane In methanol at 50℃; for 2h; chemoselective reaction;56%
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
4-nitrophthalic amide
13138-53-9

4-nitrophthalic amide

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With ammonium; ammonia at 25℃; Equilibrium constant; Rate constant; Mechanism; reagent concentration, pH varied;
acidic ammonium salt of/the/ 4-nitro-phthalic acid

acidic ammonium salt of/the/ 4-nitro-phthalic acid

4-nitrophthalimide
89-40-7

4-nitrophthalimide

4-nitrophthalic anhydride
5466-84-2

4-nitrophthalic anhydride

ammonium carbonate

ammonium carbonate

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
at 220 - 230℃;
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

ammonium carbonate

ammonium carbonate

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
at 220 - 230℃;
2-chloro-5-nitrobenzoic acid
2516-96-3

2-chloro-5-nitrobenzoic acid

copper (I)-cyanide

copper (I)-cyanide

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With pyridine; 1,2-dichloro-benzene at 150 - 160℃;
4-nitrophthalic acid
610-27-5

4-nitrophthalic acid

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Ac2O / Heating
2: 64 percent / formamide / 0.05 h / microwave irradiation
View Scheme
Multi-step reaction with 2 steps
2: 220 - 230 °C
View Scheme
With ammonium carbonate at 220 - 230℃; for 1h;
With acetic acid; urea at 110℃; for 5h;
phthalic anhydride
85-44-9

phthalic anhydride

4-nitrophthalimide
89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: urea
2: nitric acid
View Scheme
Multi-step reaction with 2 steps
1: 0.08 h / 125 °C / Microwave irradiation
2: sulfuric acid; nitric acid / 4 h / 5 - 20 °C
View Scheme
4-nitrophthalimide
89-40-7

4-nitrophthalimide

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 5-nitro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate

tert-butyl 5-nitro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile100%
With dmap In acetonitrile at 20℃;
vinyl acetate
108-05-4

vinyl acetate

4-nitrophthalimide
89-40-7

4-nitrophthalimide

5-nitro-2-vinylisoindoline-1,3-dione
89024-41-9

5-nitro-2-vinylisoindoline-1,3-dione

Conditions
ConditionsYield
With lithium chloride; palladium dichloride for 20h; Inert atmosphere; Reflux;100%
With lithium chloride; palladium dichloride for 20h; Reflux;100%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

N-iodo-4-nitrophthalimide

N-iodo-4-nitrophthalimide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In acetonitrile at 20℃; for 4h;100%
With [bis(acetoxy)iodo]benzene; iodine In acetonitrile at 20℃; for 6h; Inert atmosphere;100%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

4-nitrophthalic amide
13138-53-9

4-nitrophthalic amide

Conditions
ConditionsYield
With ammonium hydroxide 1.) 6 h, 2.) 0 deg C, 19 h;99%
With ammonia In methanol at -78℃;98%
With hydroxylamine95%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

4-aminophthalimide
3676-85-5

4-aminophthalimide

Conditions
ConditionsYield
With hydrogen; nickel In DMF (N,N-dimethyl-formamide) at 20 - 50℃; under 1034.32 - 3102.97 Torr;97%
With hydrogen; 5% Pd(II)/C(eggshell) In ethyl acetate97%
With palladium 10% on activated carbon; ammonium formate; silica gel In methanol for 1.5h; Milling;97%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

4-nitrophthalimide
89-40-7

4-nitrophthalimide

tert-butyl 2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetate
1038103-17-1

tert-butyl 2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 3h; Reflux;96%
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 3h; Reflux;96%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

sodium phenoxide
139-02-6

sodium phenoxide

4-phenoxy-phthalimide
301208-03-7

4-phenoxy-phthalimide

Conditions
ConditionsYield
In dimethyl sulfoxide at 15 - 120℃; for 24h; Solvent; Inert atmosphere;96%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

1-chloro-5-nitroisoindoline-1,3-dione
63571-79-9

1-chloro-5-nitroisoindoline-1,3-dione

Conditions
ConditionsYield
With trichloroisocyanuric acid In water at 22℃; for 1h;96%
allyl iodid
556-56-9

allyl iodid

4-nitrophthalimide
89-40-7

4-nitrophthalimide

N-allyl-4-nitrophthalimide
60283-85-4

N-allyl-4-nitrophthalimide

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 5h; Inert atmosphere; Reflux; chemoselective reaction;95%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

urea
57-13-6

urea

copper(l) chloride

copper(l) chloride

copper-2,9,16,23-tetranitrophthalocyanine

copper-2,9,16,23-tetranitrophthalocyanine

Conditions
ConditionsYield
In 1,2-dichloro-benzene Reflux;93%
...Expand
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

4-nitrophthalimide
89-40-7

4-nitrophthalimide

N-[(5-nitro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N-methylacetamide
1401870-85-6

N-[(5-nitro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-N-methylacetamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium iodide In water at 90℃; for 12h;93%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

methyl iodide
74-88-4

methyl iodide

4-nitro-N-methyl-phthalimide
41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 5h; Inert atmosphere; Reflux; chemoselective reaction;91%
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 1h;60%
With potassium carbonate; N,N-dimethyl-formamide at 135 - 145℃;
With potassium carbonate In N,N-dimethyl-formamide at 70 - 110℃; Inert atmosphere;
4-nitrophthalimide
89-40-7

4-nitrophthalimide

toluene
108-88-3

toluene

5-(benzylamino)isoindoline-1,3-dione

5-(benzylamino)isoindoline-1,3-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; hydrogen In water; toluene at 160℃; under 30003 Torr; for 36h; Autoclave;90%
Quinuclidine
100-76-5

Quinuclidine

4-nitrophthalimide
89-40-7

4-nitrophthalimide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

5-nitro-2-(2-(1-phenylpiperidin-4-yl)ethyl)isoindoline-1,3-dione

5-nitro-2-(2-(1-phenylpiperidin-4-yl)ethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
Stage #1: Quinuclidine; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4-nitrophthalimide In tetrahydrofuran at 80℃; for 18h; Inert atmosphere;		90%
...Expand
4-nitrophthalimide
89-40-7

4-nitrophthalimide

phenol potassium fluoride

phenol potassium fluoride

4-phenoxy-phthalimide
301208-03-7

4-phenoxy-phthalimide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 15 - 120℃; for 24h; Inert atmosphere;89%
3-iodo-2-chloropropene
39557-31-8

3-iodo-2-chloropropene

4-nitrophthalimide
89-40-7

4-nitrophthalimide

N-(2-chloroallyl)-4-nitrophthalimide
83051-22-3

N-(2-chloroallyl)-4-nitrophthalimide

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 6h; Inert atmosphere; Reflux; chemoselective reaction;87%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

benzene
71-43-2

benzene

4-nitro-N-phenylphthalimide
40392-27-6

4-nitro-N-phenylphthalimide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 140℃; for 4h;87%
With [bis(acetoxy)iodo]benzene at 145℃; for 3h; Microwave irradiation;40%
nitrostyrene
5153-67-3

nitrostyrene

4-nitrophthalimide
89-40-7

4-nitrophthalimide

5-nitro-2-(2-nitro-1-phenylethyl)isoindoline-1,3-dione
1426904-53-1

5-nitro-2-(2-nitro-1-phenylethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With TEA In dichloromethane at 20℃; for 24h; Michael Addition;87%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

ethyl Phenylphosphinate
172487-18-2

ethyl Phenylphosphinate

ethyl (5-nitro-1,3-dioxoisoindolin-2-yl)(phenyl)phosphinate

ethyl (5-nitro-1,3-dioxoisoindolin-2-yl)(phenyl)phosphinate

Conditions
ConditionsYield
Stage #1: 4-nitrophthalimide With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; Green chemistry;
Stage #2: ethyl Phenylphosphinate In acetonitrile at 0℃; for 0.166667h; Green chemistry;		87%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

Hexakis(4-aminophenoxy)cyclotriphosphazene
13441-26-4

Hexakis(4-aminophenoxy)cyclotriphosphazene

Hexakis<4-(4'-nitrophthalimido)phenoxy>cyclotriphosphazene
142960-23-4

Hexakis<4-(4'-nitrophthalimido)phenoxy>cyclotriphosphazene

Conditions
ConditionsYield
With phenol In toluene Heating;86%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

4-nitro-N-methyl-phthalimide
41663-84-7

4-nitro-N-methyl-phthalimide

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In N,N-dimethyl-formamide at 95℃; for 12h;86%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

cyclopentene
142-29-0

cyclopentene

C13H12N2O2

C13H12N2O2

Conditions
ConditionsYield
With tert.-butylhydroperoxide; hydrogen In water; toluene at 160℃; under 30003 Torr; for 36h; Autoclave;84%
formaldehyd
50-00-0

formaldehyd

4-nitrophthalimide
89-40-7

4-nitrophthalimide

N-hydroxymethyl-3-nitrophthalimide
22546-83-4

N-hydroxymethyl-3-nitrophthalimide

Conditions
ConditionsYield
In water for 0.4h; hydroxymethylation; Heating; ultrasound irradiation;83%
In water for 3h; Reflux;77%
In water; N,N-dimethyl-formamide for 0.0333333h; microwave irradiation;69%
With water; N,N-dimethyl-formamide
In 1,4-dioxane; water for 7h; Reflux;
4-nitrophthalimide
89-40-7

4-nitrophthalimide

cyclopentene
142-29-0

cyclopentene

2-(cyclopent-2-enyl)-5-nitroisoindoline-1,3-dione

2-(cyclopent-2-enyl)-5-nitroisoindoline-1,3-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane; benzene at 80℃; for 12h; Schlenk technique; Sealed tube; regioselective reaction;83%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

4-[bis(2-hydroxyethyl)amino]-4'-nitrostilbene
117563-47-0

4-[bis(2-hydroxyethyl)amino]-4'-nitrostilbene

4-{bis[2-(4-nitrophthalimido)ethyl]amino}-4'-nitrostilbene
251452-76-3

4-{bis[2-(4-nitrophthalimido)ethyl]amino}-4'-nitrostilbene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h; Mitsunobu reaction;81.4%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

acetone
67-64-1

acetone

5-nitro-2-(2-oxopropyl)isoindoline-1,3-dione
807335-54-2

5-nitro-2-(2-oxopropyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane; ethyl acetate at 130℃; for 3h; Sealed tube;81%
4-nitrophthalimide
89-40-7

4-nitrophthalimide

propyl bromide
106-94-5

propyl bromide

4-nitro-N-ethylphthalimide
55080-56-3

4-nitro-N-ethylphthalimide

Conditions
ConditionsYield
Stage #1: 4-nitrophthalimide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;
Stage #2: propyl bromide In N,N-dimethyl-formamide at 60℃; for 6h;		81%

4-Nitrophthalimide Chemical Properties

Molecule structure of 4-Nitrophthalimide (CAS NO.89-40-7):

IUPAC Name: 5-Nitroisoindole-1,3-dione 
Molecular Weight: 192.12836 g/mol
Molecular Formula: C8H4N2O4 
Density: 1.609 g/cm3 
Melting Point: 206 °C
Index of Refraction: 1.657
Molar Refractivity: 43.97 cm3
Molar Volume: 119.3 cm3
Polarizability: 17.43×10-24 cm3
Surface Tension: 72.2 dyne/cm 
Water Solubility: <0.01 g/100 mL at 18 °C
XLogP3: 1
H-Bond Donor: 1
H-Bond Acceptor: 4
Tautomer Count: 3
Exact Mass: 192.017107
MonoIsotopic Mass: 192.017107
Topological Polar Surface Area: 89.3
Heavy Atom Count: 14
Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=O)NC2=O
InChI: InChI=1S/C8H4N2O4/c11-7-5-2-1-4(10(13)14)3-6(5)8(12)9-7/h1-3H,(H,9,11,12)
InChIKey: ANYWGXDASKQYAD-UHFFFAOYSA-N
EINECS: 201-905-5
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; N; Stains and Dyes; Stains&Dyes, A to 

4-Nitrophthalimide Uses

 4-Nitrophthalimide (89-40-7) can be used for  intermediates of organic synthesis and fluorescent dye.

4-Nitrophthalimide Production

The product is derived by nitration of phthalimide.

4-Nitrophthalimide Toxicity Data With Reference

1.    

mmo-sat 333 µg/plate

     EMMUEG    Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1.

4-Nitrophthalimide Consensus Reports

Reported in EPA TSCA Inventory.

4-Nitrophthalimide Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 37/39-26-36 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RTECS: TI5625000
Hazard Note: Irritant
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

4-Nitrophthalimide Specification

 4-Nitrophthalimide (CAS NO.89-40-7) is also named as 1H-Isoindole-1,3(2H)-dione, 5-nitro- ; 5-21-11-00158 (Beilstein Handbook Reference) ; 5-Nitrophthalimide ; AI3-00701 ; BRN 0180224 ; CCRIS 4685 ; NSC 5394 . 4-Nitrophthalimide (CAS NO.89-40-7) is slight yellow powder. It is insoluble in water and can be hydrolyzed. It is a nitrated amine. Amines are chemical bases and combustible. The combustion of amines yields noxious NOx. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View