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

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

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 
• 160557-04-0 (2S,4R)-3-benzoyl-4-butyl-2-phenyl-4-phthalimidomethyloxazolidin-5-one 
• 4731-71-9 diphenyl(N-phthalimidomethyl)phosphine oxide 

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.

Synthesis and Characterization of Novel Phthalimide-pyrano[3,2-c]chromene and Phthalimide-pyrano-2-one Hybrids

Coumarin skelton holds substantial promise for further exploration because of its immense pharmacological potential. In this pursuit, a series of phthalimide-chromen and phthalimide-pyran-2-one hybrids were synthesized in efficient yields via one-pot multicomponent reaction of aldehyde linked to phthalimide moiety, 4-hydroxy coumarin/4-hydroxy-6-methyl-2H-pyran-2-one, and malanonitrile by Knoevenagel reaction at room temperature in the presence of DABCO as catalyst. The compounds were characterized by 1H NMR and 13C NMR, MS, and FTIR. All the compounds consisting of phthalimide-chromen/pyrano-2-one moieties tethered by spacers of varying lengths were evaluated for their biological activity in Ellman's assay. Most of the compounds feebly inhibited Acetylcholinesterase Enzyme and were inactive toward Butyrylcholinesterase Enzyme.

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.