2439-85-2

Basic information

• Product Name: N-BROMOPHTHALIMIDE
• Synonyms: N-BROMOPHTHALIMIDE;N-Bromophthalimide, 98+%;N-Bromophthalimide,95%;1H-Isoindole-1,3(2H)-dione,2-broMo-;2-broMoisoindoline-1,3-dione;NSC 3525;N-Bromophthalimide 95%;N-Bromophthalimide≥ 98%(Titration)
• CAS NO: 2439-85-2
• Molecular Formula: C₈H₄BrNO₂
• Molecular Weight: 226.03
• EINECS: 219-467-9
• Product Categories: Miscellaneous;Bromination;Halogenation;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Synthetic Organic Chemistry;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 2439-85-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 194-198 °C(lit.)
• Boiling Point: 332.3 °C at 760 mmHg
• Flash Point: 154.8 °C
• Appearance: off-white powder.
• Density: 1.932 g/cm³
• Vapor Pressure: 0.000147mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -3.53±0.20(Predicted)
• Sensitive: Moisture & Light Sensitive
• BRN: 131211
• CAS DataBase Reference: N-BROMOPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BROMOPHTHALIMIDE(2439-85-2)
• EPA Substance Registry System: N-BROMOPHTHALIMIDE(2439-85-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 2439-85-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow to yellow powder

Uses

Different sources of media describe the Uses of 2439-85-2 differently. You can refer to the following data:
1. Brominating agent.
2. N-Bromophthalimide has been used:as reagent in allylic amination reactions of alkenesbrominating reagent in enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric brominationas a titrant in titrimetric determination of isoniazid in pure form or in tablets
3. N-BROMOPHTHALIMIDE (cas# 2439-85-2) is a useful catalyst for reactions such as the Hofmann-?Loffler reactions of sulfonimides under visible Light and the synthesis of naphthols via bromide-mediated intermolecular annulation.

InChI:InChI=1/C8H4BrNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H

Upstream product

• 136918-14-4 phthalimide 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 33081-78-6 sodium phthalimide 
• 7732-18-5 water 
• 124782-44-1 diphenylantimony(III) phthalimide 
• 86451-26-5 2,2'-(phenyl-λ³-iodanediyl)bis(isoindoline-1,3-dione) 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 7143-42-2 methyl 2-((methoxycarbonyl)amino)benzoate 
• 70767-39-4 6-bromo-1-chlorocyclohex-1-ene 
• 1452-34-2 2α-bromo-5α-cholestan-3-one 
• 5680-61-5 diethyl 2-phthalimidomalonate 
• 136918-14-4 phthalimide 
• 632-56-4 tetraethyl ethane-1,1,2,2-tetracarboxylate 
• 58174-87-1 2-(4-nitro-phenyl)-3,5-diphenyl-tetrazolium; bromide 
• 108516-76-3 5-chloro-3β-acetoxy-24.24-diphenyl-5α-choladiene-(20(22)ξ.23) 
• 82426-77-5 3α,12α-diacetoxy-24,24-diphenyl-5β-choladiene-(20(22)ξ,23) 
• 108890-73-9 ethyl 2-((ethoxycarbonyl)amino)benzoate 
• 2049-86-7 Diethyl 2,3-diacetylsuccinate 
• 615-57-6 2,4-dibromo-aniline 
• 100-39-0 benzyl bromide 
• 6165-62-4 5-p-nitrophenyl-2,3-diphenyltetrazolium chloride 

Relevant articles and documents

Photochemical regioselective C(sp3)-H amination of amides using N-haloimides

A metal-free regioselective C(sp3)-H amination of amides using N-haloimides in the presence of lithium tert-butoxide and visible light is presented herein. This photoexcited approach is straightforward, and it aminates a wide variety of amides under mild conditions without the use of photocatalysts, external radical initiators, or oxidants. A halogen-bonded intermediate between the tert-butoxide base and the N-haloimide is proposed to be responsible for the increased photoreactivity. Calculations show that the formation of this electron donor-acceptor complex presents an exergonic energy profile.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate

AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.