5332-26-3

Basic information

• Product Name: N-(Bromomethyl)phthalimide
• Synonyms: N-(BROMOMETHYL)PHTALIMIDE;N-(BROMOMETHYL)PHTHALIMIDE;N-PHTHALIMIDOMETHYL BROMIDE;PHTHALIMIDOMETHYL BROMIDE;1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-;2-(Bromomethyl)-1H-isoindole-1,3(2H)-dione;2-(bromomethyl)-1h-isoindole-3(2h)-dione;Phthalimide, N-(bromomethyl)-
• CAS NO: 5332-26-3
• Molecular Formula: C₉H₆BrNO₂
• Molecular Weight: 240.05
• EINECS: 226-239-2
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides
• Mol File: 5332-26-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 152-155 °C(lit.)
• Boiling Point: 318.9 °C at 760 mmHg
• Flash Point: 146.7 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.6838 (rough estimate)
• Vapor Pressure: 3.94E-07mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: -2.72±0.20(Predicted)
• Water Solubility: decomposes
• Sensitive: Moisture & Light Sensitive
• BRN: 140943
• CAS DataBase Reference: N-(Bromomethyl)phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Bromomethyl)phthalimide(5332-26-3)
• EPA Substance Registry System: N-(Bromomethyl)phthalimide(5332-26-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 8-10-21
• TSCA: Yes
• Hazardous Substances Data: 5332-26-3(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

N-(Bromomethyl)phthalimide was used as initiator in synthesis of α-phthalimidopoly(styrene) by atom transfer radical polymerisation. It was also used in synthesis of functionalized 5-(aminomethyl)pyrimidine-2,4,6-trione analog and new bis-C(cage)-substituted o-carborane.

InChI:InChI=1/C9H8BrNO2/c10-5-9-4-2-1-3-6(9)7(12)11-8(9)13/h1-4,6H,5H2,(H,11,12,13)

Upstream product

• 550-44-7 N-methylphthalimide 
• 1074-82-4 potassium phtalimide 
• 74-95-3 1,1-dibromomethane 
• 136918-14-4 phthalimide 
• 496-11-7 INDANE 
• 85-44-9 phthalic anhydride 
• 4702-13-0 N-phthaloylglycine 
• 118-29-6 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione 
• 7726-95-6 bromine 
• 7647-01-0 hydrogenchloride 
• 10035-10-6 hydrogen bromide 

Downstream Products

• 109091-43-2 (2-phthalimidomethyl-phenyl)-acetic acid 
• 109093-38-1 (4-phthalimidomethyl-phenyl)-acetic acid 
• 53497-63-5 N-phenethyloxymethyl-phthalimide 
• 6119-96-6 dithiophosphoric acid O,O'-diethyl ester-S-phthalimidomethyl ester 
• 64039-42-5 (1,3-dioxoisoindolin-2-yl)methyl carbamimidothioate hydrobromide 
• 13314-96-0 2-((phenylamino)methyl)isoindoline-1,3-dione 
• 71858-47-4 N-(4-nitro-phenylsulfanylmethyl)-phthalimide 
• 54399-24-5 2-<(cyclohexyloxy)methyl>-isoindole-1,3(2H)-dione 
• 1066-51-9 Aminomethylphosphonic acid 
• 24124-24-1 2-(4-Hydroxybenzyl)isoindole-1,3-dione 
• 82356-36-3 N-salicyl-phthalimide 
• 118-29-6 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione 
• 19443-80-2 6β-(2-phenyl-acetylamino)-penicillanic acid phthalimidomethyl ester 
• 54399-22-3 2-<(diphenylmethyloxy)methyl>-isoindole-1,3(2H)-dione 

Relevant articles and documents

Synthesis method N - bromomethylphthalimide

The invention discloses a synthesis method N -bromomethylphthalimide, which uses N - hydroxymethyl phthalimide in an inert solvent and bromination reaction of phosphorus tribromide to obtain N -bromomethylphthalimide. To the invention, the reaction is complete by equimolar or slightly excess phosphorus tribromide, the utilization rate of the raw material bromine atom is greatly improved, the three-waste emission is reduced, the production efficiency is improved, and the production cost is reduced. The mother liquor can be directly sheathed into the next batch of feeding. The by-product phosphorous acid is sold as a byproduct, the process itself realizes zero release, and the sustainable development direction of clean production is represented.

Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme

Installation of olefins into molecules is a key transformation in organic synthesis. The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. This method is commonly employed in natural product biosynthesis. Herein, we demonstrate that a ferryl intermediate is used for C-H activation at the benzylic position of the substrate. We further establish that P.IsnB reactivity can be switched from olefination to hydroxylation using electron-withdrawing groups appended on the phenyl moiety of the analogues. These experimental observations imply that a pathway involving an initial C-H activation followed by a benzylic carbocation species or by electron transfer coupled β-scission is likely utilized to complete C=C bond formation.

Synthesis, structural and antioxidant studies of some novel N-ethyl phthalimide esters

A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity.