4-Nitrophthalic anhydride Property

Melting point:

116-120 °C(lit.)

Boiling point:

197 °C / 8mmHg

Density 

1.6392 (rough estimate)

refractive index 

1.4700 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Beige

Water Solubility 

Hydrolysis

Sensitive 

Moisture Sensitive

BRN 

179682

CAS DataBase Reference

5466-84-2(CAS DataBase Reference)

NIST Chemistry Reference

4-Nitrophthalic anhydride(5466-84-2)

EPA Substance Registry System

5-Nitrophthalic anhydride (5466-84-2)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/22

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

RTECS 

TI3328000

F 

10-21

TSCA 

Yes

HS Code 

29173990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Nitrophthalic anhydride Chemical Properties,Usage,Production

Chemical Properties

off-white to light yellow-brown powder. Soluble in hot alcohol, hot acetic acid and acetone, insoluble in water.

Uses

4-Nitrophthalic anhydride is used an an intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472).

Uses

5-Nitrophthalic Anhydride is used in the preparation of phthalic acids as well as compounds with anticonvulsant activities.

Preparation

4-Nitrophthalic anhydride is synthesized by hydrolysis of 4-nitrophthalimide and then dehydration. The 4-nitrophthalimide was added to the sodium hydroxide solution, heated and boiled for 15min. Adjust pH to 6-8 with nitric acid, and add nitric acid to boil for 5 min. Cooling, filtering, the filtrate was extracted with ether, the extract was dried and then the ether was evaporated, that is, 4-Nitrophthalic anhydride crystals were precipitated. Yield 95%.

General Description

Yellow powder.

Air & Water Reactions

Reacts with water. The organic acids produced by this reaction are significantly more soluble in water.

Reactivity Profile

4-Nitrophthalic anhydride reacts exothermically with water. The reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Fire Hazard

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

Purification Methods

Distil the anhydride in a vacuum and/or recrystallise it from *C6H6 or Et2O/pet ether. Dry it in vacuo. It forms addition compounds with anthracene (m 118o), and phenanthrene (m 96o). [Beilstein 17 III/IV 6150, 17/11 V 267.]

Precautions

Moisture Sensitive. Store away from strong bases and oxidizing agents. Incompatible with water, bases, strong acids and oxidizing agents.