Phthalimide Property

Melting point:

232-235 °C(lit.)

Boiling point:

366 °C

Density 

1.21

vapor pressure 

0.001Pa at 25℃

refractive index 

1.4700 (estimate)

Flash point:

165 °C

storage temp. 

Store below +30°C.

solubility 

water: slightly soluble(lit.)

pka

8.3(at 25℃)

form 

Crystalline Flakes

color 

White to slightly yellow

PH

3.8 (0.6g/l, H2O)

Water Solubility 

<0.1 g/100 mL at 19.5 ºC

Sublimation 

366 ºC

Merck 

14,7373

BRN 

118522

InChIKey

XKJCHHZQLQNZHY-UHFFFAOYSA-N

LogP

1.15

CAS DataBase Reference

85-41-6(CAS DataBase Reference)

NIST Chemistry Reference

Phthalimide(85-41-6)

EPA Substance Registry System

Phthalimide (85-41-6)

Safety

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

22-24/25

WGK Germany 

1

RTECS 

TI3920000

Autoignition Temperature

>500 °C

TSCA 

Yes

HS Code 

29251995

Hazardous Substances Data

85-41-6(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 7940 mg/kg

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Phthalimide Chemical Properties,Usage,Production

Chemical Properties

white to slightly yellowish crystalline flakes

Uses

Phthalimide, C6H4(CO)2NH, is an imide of commercial and industrial importance, forming a number of interesting derivatives. With alcoholic potash, phthalimide forms a potassium derivative, C6H4 (CO)2 NK, which, when reacted with ethyl iodide (or other alkyl halides), yields ethylphthalimide, C6H4(CO)2 N C2H5. The latter product, when hydrolyzed with an acid or alkali, further yields ethylamine [CAS: 75-04-7] C2H7N. Such reaction chains are useful in the preparation of certain primary amines and their derivatives.

Uses

Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide spectrum of applications as anti-convulsant, anti-inflammatory, analgesic, hypolipidimic and immunomodulatory activities. Dyes and metabolites, Environmental Testing.

Definition

ChEBI: A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.

Synthesis Reference(s)

Journal of the American Chemical Society, 111, p. 3725, 1989 DOI: 10.1021/ja00192a034
The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038
Tetrahedron Letters, 34, p. 6907, 1993 DOI: 10.1016/S0040-4039(00)91827-6

General Description

White to light tan powder. Slightly acidic.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

O-Phthalimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). O-Phthalimide forms salts with bases.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition O-Phthalimide emits toxic fumes of nitrogen oxides.

Fire Hazard

Literature sources indicate that O-Phthalimide is combustible.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise the imide from EtOH (20mL/g) (charcoal), or sublime it. For potassium phthalimide see entry in “Metal-organic Compounds”, Chapter 5. [Beilstein 21/10 V 270.]