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4-Nitrophthalimide

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Name

4-Nitrophthalimide

EINECS 201-905-5
CAS No. 89-40-7 Density 1.609 g/cm3
PSA 91.99000 LogP 1.33040
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 N/A
Transport Information N/A 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);

Article Data 59

4-Nitrophthalimide Synthetic route

5466-84-2

4-nitrophthalic anhydride

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;
136918-14-4

phthalimide

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%
22246-24-8

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

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%
73097-02-6

ethyl 2-chloro-4-nitrobenzoate

544-92-3

copper(I) cyanide

A

ethyl 2-cyano-4-nitro-benzoate

B

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
105969-98-0

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

89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
With potassium acetate; bis(pinacol)diborane In methanol at 50℃; for 2h; chemoselective reaction;56%
46053-72-9

5-nitroisoindoline

A

89-40-7

4-nitrophthalimide

B

610-27-5

4-nitrophthalic acid

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid
13138-53-9

4-nitrophthalic amide

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

89-40-7

4-nitrophthalimide

5466-84-2

4-nitrophthalic anhydride

ammonium carbonate

ammonium carbonate

89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
at 220 - 230℃;
610-27-5

4-nitrophthalic acid

ammonium carbonate

ammonium carbonate

89-40-7

4-nitrophthalimide

Conditions
ConditionsYield
at 220 - 230℃;

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.

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