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85-41-6

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Identification

Name
O-Phthalimide
CAS
85-41-6
Synonyms
1,2-BENZENEDICARBOXIMIDE
1,2-PHTHALIC IMIDE
1,3-DIHYDROISOINDOLE-1,3-DIONE
1,3-ISOINDOLEDIONE
1H-ISOINDOLE-1,3(2H)-DIONE
ISOINDOLE-1,3-DIONE
LABOTEST-BB LTBB000782
O-PHTHALIC IMIDE
o-Phthalimide
Phenylimide
PHTHALIC ACID IMIDE
phthalic dicarboximide
PHTHALIMIDE
1,3-Isoindolinedione
2-Diazoindan-1,3-dione
Benzoimide
Ftalimmide
Phthalimid
PHTHALYLIMIDE
2,5-Isoindoledione
EINECS(EC#)
201-603-3
Molecular Formula
C12H8N2O6
MDL Number
MFCD08448696
Molecular Weight
276.2
MOL File
85-41-6.mol

Chemical Properties

Appearance
white to slightly yellowish crystalline flakes
Melting point 
232-235 °C(lit.)

mp 
232-235 °C(lit.)

Boiling point 
366 °C
bp 
366 °C
density 
1.21
refractive index 
1.4700 (estimate)
Fp 
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
CAS DataBase Reference
85-41-6(CAS DataBase Reference)
NIST Chemistry Reference
Phthalimide(85-41-6)
EPA Substance Registry System
85-41-6(EPA Substance)

Safety Data

Risk Statements 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect.
Safety Statements 
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
WGK Germany 
1

RTECS 
TI3920000

Autoignition Temperature
>500 °C
TSCA 
Yes
HS Code 
29251995
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.
Hazardous Substances Data
85-41-6(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 7940 mg/kg

Raw materials And Preparation Products

Hazard Information

General Description
White to light tan powder. Slightly acidic.
Reactivity Profile
PHTHALIMIDE(85-41-6) 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). This chemical forms salts with bases.
Air & Water Reactions
Insoluble in water.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides.
Fire Hazard
Literature sources indicate that this compound is combustible.
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
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.]

Material Safety Data Sheet(MSDS)

msds information
Phthalimide(85-41-6).msds

Spectrum Detail

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