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

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

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

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

Downstream Products

• 136918-14-4 phthalimide 
• 100-52-7 benzaldehyde 
• 7143-42-2 methyl 2-((methoxycarbonyl)amino)benzoate 
• 7764-29-6 N,N'-thiobisphthalimide 
• 520-03-6 N-phenylphthalimide 
• 75784-55-3 (p-bromomethylphenyl)diphenylphosphine oxide 
• 94396-54-0 1-O-acetyl-2,5,6-tri-O-benzoyl-4-hydroxy-3,4-O-(α-phthalimidobenzylidene)-β-D-galactofuranose 
• 94396-42-6 1-O-acetyl-2,3,5,6-tetra-O-benzoyl-4-bromo-β-D-galactofuranose 
• 14204-26-3 N-(benzylthio)phthalimide 
• 118-92-3 anthranilic acid 
• 118-79-6 2,4,6-tribromophenol 
• 632-56-4 tetraethyl ethane-1,1,2,2-tetracarboxylate 
• 17345-73-2 4,6-dibromo-pyrogallol 
• 5401-62-7 1,2-dibromocyclohexane 

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.

Preparation method of 3,5-dibromo-2-aminobenzoic acid

The invention discloses a preparation method of 3,5-dibromo-2-aminobenzoic acid. The preparation method comprises the following steps: (I) performing in-situ oxidation on bromide with an oxidant underan acidic condition, and carrying out a bromination reaction on phthalimide to obtain N-bromophthalimide; (II) performing Hoffmann degradation on the N-bromophthalimide under the action of alkali toobtain 2-aminobenzoic acid and bromoanion; (III) further adding an appropriate amount of bromide and oxidant, and carrying out a bromination reaction on the 2-aminobenzoic acid to obtain the product,namely, 3,5-dibromo-2-aminobenzoic acid. The preparation method has the advantages of environment-friendly reaction system, simple, convenient and safe reaction operation, low cost, high reaction selectivity and high product yield and the like.

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.

α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions

In this work, we introduce a new class of halodiazocarbonyl compounds, α-halodiazoacetamides, which through a metal-free, ambient-temperature thermolysis perform intramolecular C-H insertions to produce α-halo-β-lactams. When carried out with α-bromodiazoacetamides bearing cyclic side chains, the thermolysis reaction affords bicyclic α-halo-β-lactams, in some cases in excellent yields, depending on the ring size and substitution pattern of the cyclic amide side chains.

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.

Organic Synthesis Using Sodium Bromate. II. A Facile Synthesis of N-Bromo Imides and Amides Using Sodium Bromate and Hydrobromic Acid (or Sodium Bromide) in the Presence of Sulfuric Acid

The reaction of imides and amides in water (or aqueous acetic acid) with sodium bromate and hydrobromic acid (or sodium bromide) in the presence of sulfuric acid under mild conditions gave the corresponding N-bromides in high yields.

Imidyl Radicals. The Chemistries of 1,8-Naphthalenedicarboximidyl and Phthalimidyl Radicals

The chemistries of 1,8-naphthalenedicarboximidyl (N.) and phthalimidyl (P.) radicals are described.Hydrogen abstractions from alkanes and additions to olefins and benzene proceed in high yield.The low cost of phthalimide, coupled with the absence of a parasitic ring-opening reaction for P., makes N-bromophthalimide an economical reagent for low-selectivity brominations.The chemistry of N. resembles that of other imidyl radicals (succinimidyl, glutarimidyl) with respect to selectivities.Conversely, P. is somewhat of a maverick among imidyl radicals, being slightly more selective in its reactions, but still 102-103 less selective than Br..

A Practical Synthesis of N-Bromo Imides by Use of Sodium Bromite

N-Bromo imides can be readily prepared under mild conditions by a reaction of imides with sodium bromite in the presence of hydrobromic acid in fairly good yields.The scope and limitation are also presented.

TIN(IV) MEDIATED SYNTHESIS OF N-HALO COMPOUNDS

Some representative N-halo compounds like N-bromosuccinimide, N-iodosuccinimide, N-bromophthalimide, N-iodophthalimide, N-iodobenzimidazole and N-iodobenzotriazole have been synthesised in good yields under neutral and mild conditions via an intermediate formed from the parent NH species and bis(tri-n-butyltin) oxide.The tin oxide is recovered as recyclable tri-n-butyltin halide.