85-41-6 Usage
Chemical Properties
white to slightly yellowish crystalline flakes
Uses
Different sources of media describe the Uses of 85-41-6 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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/ja00192a034The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038Tetrahedron 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 85-41-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 5 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 85-41:
(4*8)+(3*5)+(2*4)+(1*1)=56
56 % 10 = 6
So 85-41-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11)
85-41-6Relevant articles and documents
Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones
Tnay, Ya Lin,Chiba, Shunsuke
, p. 873 - 877 (2015)
The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.
PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
supporting information, p. 1180 - 1185 (2019/01/26)
A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.
A Novel Green Synthesis of Thalidomide and Analogs
Benjamin, Ellis,Hijji, Yousef M.
, (2017/09/19)
Thalidomide and its derivatives are currently under investigation for their antiangiogenic, immunomodulative, and anticancer properties. Current methods used to synthesize these compounds involve multiple steps and extensive workup procedures. Described herein is an efficient microwave irradiation green synthesis method that allows preparation of thalidomide and its analogs in a one-pot multicomponent synthesis system. The multicomponent synthesis system developed involves an array of cyclic anhydrides, glutamic acid, and ammonium chloride in the presence of catalytic amounts of 4-N,N-dimethylaminopyridine (DMAP) to produce thalidomide and structurally related compounds within minutes in good isolated yields.