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Phthalimide

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Phthalimide Basic information

Product Name:
Phthalimide
Synonyms:
  • Potassium phthalylimide
  • LABOTEST-BB LTBB000782
  • ISOINDOLE-1,3-DIONE
  • 1,3-dihydro-1,3-dioxoisoindole
  • PHTHALIMIDE,REAGENT
  • PHTHALIMIDE / 2,5-ISOINDOLEDIONE
  • 2H-Isoindole-1,3-dione
  • Isoindoline-1,3-dione
CAS:
85-41-6
MF:
C8H5NO2
MW:
147.13
EINECS:
201-603-3
Product Categories:
  • Thiazines ,Thiophenes ,Thiazoles
  • intermediates
  • pharmacetical
  • API intermediates
Mol File:
85-41-6.mol
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Phthalimide Chemical Properties

Melting point:
232-235 °C(lit.)
Boiling point:
366 °C
Density 
1.21
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
Merck 
14,7373
Sublimation 
366 ºC
BRN 
118522
InChIKey
XKJCHHZQLQNZHY-UHFFFAOYSA-N
CAS DataBase Reference
85-41-6(CAS DataBase Reference)
NIST Chemistry Reference
Phthalimide(85-41-6)
EPA Substance Registry System
Phthalimide (85-41-6)
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Safety Information

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

MSDS

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Phthalimide Usage And Synthesis

Chemical Properties

white to slightly yellowish crystalline flakes

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.

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.

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.]

PhthalimideSupplier

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