14737-80-5

Basic information

• Product Name: 3,4,5,6-Tetrachloro-N-methylphthalimide
• Synonyms: 3(2H)-dione,4,5,6,7-tetrachloro-2-methyl-1H-Isoindole-1;4,5,6,7-tetrachloro-2-methyl-1h-isoindole-3(2h)-dione;N-Methyl-3,4,5,6-tetrachlorophthalimide;N-METHYLTETRACHLOROPHTHALIMIDE;3,4,5,6-tetrachloro-N-methylphthalimide;1H-Isoindole-1,3(2H)-dione, 4,5,6,7-tetrachloro-2-methyl-;2-Methyl-4,5,6,7-tetrachloro-isoindoline-1,3-dione;4,5,6,7-Tetrachloro-2-methyl-1H-isoindole-1,3(2H)-dione
• CAS NO: 14737-80-5
• Molecular Formula: C₉H₃Cl₄NO₂
• Molecular Weight: 298.94
• EINECS: 238-799-5
• Product Categories: Organics;API intermediates
• Mol File: 14737-80-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 210-212 °C
• Boiling Point: 433.1 °C at 760 mmHg
• Flash Point: 215.7 °C
• Appearance: /
• Density: 1.754 g/cm³
• Vapor Pressure: 1.37E-10mmHg at 25°C
• Refractive Index: 1.695
• PKA: -3.82±0.20(Predicted)
• CAS DataBase Reference: 3,4,5,6-Tetrachloro-N-methylphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6-Tetrachloro-N-methylphthalimide(14737-80-5)
• EPA Substance Registry System: 3,4,5,6-Tetrachloro-N-methylphthalimide(14737-80-5)

Safety Data

• Hazardous Substances Data: 14737-80-5(Hazardous Substances Data)

Usage

Purification Methods

Crystallise the imide from absolute EtOH. [Beilstein 21 H 505, 17/11 V 260.]

InChI:InChI=1/C8H2Cl4N2O2/c9-3-1-2(4(10)6(12)5(3)11)8(16)14(13)7(1)15/h13H2

Upstream product

• 74-88-4 methyl iodide 
• 1571-13-7 3,4,5,6-tetrachlorophthalimide 
• 74-83-9 methyl bromide 
• 88070-48-8 N-methylbenzamide 
• 117-08-8 tetrachlorophthalic anhydride 
• 74-89-5 methylamine 

Downstream Products

• 2251-54-9 3,4,6-trifluorophthalic acid 
• 446-17-3 2,4,5-trifluorobenzoic acid 
• 84863-12-7 4-(p-toluylthio)-3,5,6-trichlorophthalic acid N-methylimide 

Relevant articles and documents

Process improvements in the synthesis of 2,4,5-trifluorobenzoic acid. selective hydrodefluorination of tetrafluorophthalimides

An improved preparation of the fluoroquinolone antibacterial intermediate 2,4,5-trifluorobenzoic acid is described. A combination of a selective hydrodefluorination and hydrolysis reaction of 3,4,5,6-tetrafluoro-N-methylphthalimide leading to 3,5,6-trifluorophthalic acid was key to the success of the process. In addition the development of a two-step, one-pot imidization/ halogen exchange from tetrachlorophthalic anhydride to 3,4,5,6-tetrafluoro-N-methylphthalimide in sulfolane solvent is detailed.

Relative reactivity of methyl iodide to ethyl iodide in nucleophilic substitution reactions in acetonitrile and partial desolvation accompanying activation

Through the examination of empirical correlations involving activation parameters for nucleophilic substitution of methyl iodide and of ethyl iodide, nucleophiles have been classified into three series: (1) nucleophiles with two equivalent reaction sites, (2) nucleophiles with a chlorine atom in the para-position, and (3) nucleophiles with a single reaction site. Three types of partial desolvation processes accompanying activation have been deduced on the basis of these classifications. A major factor determining the relative reactivity of methyl iodide to ethyl iodide in the substitution reaction of an anionic nucleophile having a single reaction site in acetonitrile (kMeI/kEtI) is suggested to be partial desolvation around the nucleophilic center on going from reactant to transition-state.

HYDROLYSIS IN THE ABSENCE OF BULK WATER 1. CHEMOSELECTIVE HYDROLYSIS OF AMIDES USING TETRAHALOPHTALIC ANHYDRIDES

The reaction of primary and secondary amides with tetrafluorophthalic or tetrachlorophtalic anhydride gives carboxylic acids in good yield.The reaction is chemoselective in that the amide functionality can be hydrolyzed in the presence of ester groups.