4-Nitrophthalimide Chemical Properties

Melting point:

206 °C

Boiling point:

328.09°C (rough estimate)

Density 

1.5513 (rough estimate)

refractive index 

1.4900 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

7.79±0.20(Predicted)

color 

Yellow powder

Water Solubility 

<0.01 g/100 mL at 18 ºC

BRN 

180224

Stability:

Stable. Combustible. Incompatible with moisture, water, strong oxidising agents, strong bases.

InChIKey

ANYWGXDASKQYAD-UHFFFAOYSA-N

CAS DataBase Reference

89-40-7(CAS DataBase Reference)

NIST Chemistry Reference

4-Nitro-phthalimide(89-40-7)

EPA Substance Registry System

4-Nitrophthalimide (89-40-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36-24/25

WGK Germany 

3

RTECS 

TI5625000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29251900

Toxicity

mmo-sat 333 mg/plate EMMUEG 11(Suppl 12),1,88

MSDS

• Language:English Provider:4-Nitrophthalimide
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Nitrophthalimide Usage And Synthesis

Chemical Properties

slight yellow powder

Uses

4-Nitrophthalimide is used as intermediate of organic synthesis and fluorescent dyes, it can be used to produce azo dyes, luminol, etc. It can also be used to prepare 4-nitrophthalonitrile, 5-cyanophthalide and other drug intermediates.

Preparation

4-Nitrophthalimide is synthesized from phthalimide by nitration. Cool the fuming nitric acid to below 5°C, slowly add concentrated sulfuric acid dropwise, and control the temperature to 10-13°C. Plus phthalimide. Leave at room temperature overnight. Then, it was poured into ice water with stirring, and the precipitate was precipitated below 20°C. Filter, wash with water, dry, and then recrystallize from ethanol to obtain 4-nitrophthalimide with a yield of 60%.

General Description

Yellow powder.

Air & Water Reactions

4-Nitrophthalimide can be hydrolyzed. . Insoluble in water.

Reactivity Profile

A nitrated amine. Amines are combustible. The combustion of amines yields noxious NOx. REACTIVITY - Amines are chemical bases. 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.

Fire Hazard

Flash point data for 4-Nitrophthalimide are not available, however 4-Nitrophthalimide is probably combustible.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

Synthesis

200 mL of sulfuric acid and 50 mL of fuming nitric acid were cooled on an ice bath and 40 g (0.272 mol) phthalimide was added in portions within 1-1.5 hours so as not to exceed the internal temperature beyond 10-15 ??C. The mixture was stirred over ice bath for half an hour and the internal temperature was raised to 35 ??C, and yellow particles were observed to dissolve. The mixture was stirred for an additional 1 hour, then cooled to 0 ??C again and poured onto 1 kg of ice water mixture. Yellow 4-nitrophthalonitrile precipitated, it was filtered and washed with water until the filtrate was neutral to blue litmus paper. It was crystallized from 850-900 mL of ethyl alcohol. Bright yellow crystals were filtered, washed with cold ethyl alcohol, and dried in a vacuum oven at 80-90 ??C.

4-Nitrophthalimide(89-40-7)Related Product Information

• Phthalhydrazide
• O-Phthalimide
• 4-Aminophthalimide
• Potassium phthalimide
• N-Hydroxyphthalimide
• Succinimide
• N-Methylphthalimide
• 4-Nitro-o-phenylenediamine
• 4-Nitrophthalic acid
• 4-Nitrophthalic anhydride
• 4-Nitrophthalonitrile
• DIALIFOS
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• 4-CHLORO-5-NITROPHTHALIMIDE 98%,4-CHLORO-5-NITROPHTHALIMIDE
• N-HYDROXY-4-NITROPHTHALIMIDE
• N-METHYL-4-NITROPHTHALIMIDE
• (5-NITRO-1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)ACETIC ACID