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

Description

N-BROMOPHTHALIMIDE, with the CAS number 2439-85-2, is a pale yellow to yellow powder that serves as a versatile reagent and catalyst in various chemical reactions. It is known for its brominating properties and is widely utilized in the synthesis of different organic compounds.

Uses

1. Allylic Amination Reactions:
Used in Allylic Amination Industry
N-BROMOPHTHALIMIDE is used as a reagent for allylic amination reactions of alkenes, facilitating the formation of nitrogen-containing compounds that are essential in the pharmaceutical and agrochemical industries.
2. Enantioselective Synthesis:
Used in Enantioselective Synthesis Industry
N-BROMOPHTHALIMIDE acts as a brominating reagent in the enantioselective synthesis of multisubstituted biaryl derivatives. This process is catalyzed by chiral phosphoric acid, leading to the production of biologically active compounds with high enantiomeric purity.
3. Titrimetric Determination:
Used in Pharmaceutical Analysis Industry
N-BROMOPHTHALIMIDE is employed as a titrant in the titrimetric determination of isoniazid, a potent first-line antitubercular drug. This application helps in accurately measuring the concentration of isoniazid in pure form or in tablet formulations, ensuring the quality and efficacy of the drug.
4. Hofmann-L?ffler Reactions:
Used in Organic Synthesis Industry
N-BROMOPHTHALIMIDE serves as a useful catalyst for the Hofmann-L?ffler reactions of sulfonimides under visible light. This reaction is crucial in the synthesis of various nitrogen-containing compounds, which are vital in the pharmaceutical and agrochemical sectors.
5. Synthesis of Naphthol Derivatives:
Used in Organic Chemistry Industry
N-BROMOPHTHALIMIDE is utilized as a catalyst in the synthesis of naphthols via bromide-mediated intermolecular annulation. Naphthol derivatives are essential building blocks in the production of various pharmaceuticals, dyes, and other industrial chemicals.

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

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.