6941-75-9

Basic information

• Product Name: 4-Bromophthalimide
• Synonyms: bromophtalimide;5-bromoisoindole-1,3-dione;5-BROMO PHTHALIMIDE;4-BROMOPHTHALIMIDE;4-Bromophtalimide;4-BROMOPHTHALIMIDE 98+%;1H-Isoindole-1,3(2H)-dione, 5-broMo-;4-BroMophthaliMide, 97+%
• CAS NO: 6941-75-9
• Molecular Formula: C₈H₄BrNO₂
• Molecular Weight: 226.03
• Product Categories: Heterocycles
• Mol File: 6941-75-9.mol

Chemical Properties

• Melting Point: 235 °C
• Appearance: Off-white/Solid
• Density: 1.826g/cm³
• Refractive Index: 1.649
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in N,N-DMF almost transparency.
• PKA: 9.19±0.20(Predicted)
• CAS DataBase Reference: 4-Bromophthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophthalimide(6941-75-9)
• EPA Substance Registry System: 4-Bromophthalimide(6941-75-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 6941-75-9(Hazardous Substances Data)

Usage

Chemical Properties

yellow to slight yellow powder

Uses

It is used as a intermediate for pharmaceutical and organic synthesis.

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

Upstream product

• 583-71-1 4-bromo-o-xylene 
• 67832-11-5 4-bromo-2-methylbenzonitrile 
• 85-44-9 phthalic anhydride 

Downstream Products

• 64823-14-9 5-bromo-6-nitro-isoindole-1,3-dione 
• 490038-15-8 4-Bromophthalamid 
• 573675-39-5 5-bromo-3-hydroxyisoindoline-1-one 
• 127168-84-7 5-bromoisoindoline 
• 201940-08-1 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 905273-91-8 tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate 
• 75884-70-7 6-bromophthalazin-1(2H)-one 
• 897661-90-4 6-(4-chlorophenyl)-2H-phthalazin-1-one 
• 897661-91-5 6-(4-methoxy-2-methylphenyl)-2H-phthalazin-1-one 
• 868662-12-8 6-(4-trifluoromethylphenyl)-2H-phthalazin-1-one 
• 182296-29-3 diethyl (3,4-dicyanophenyl)phosphonate 

Relevant articles and documents

Dihydroxyphenyl Sulfonylisoindoline Derivatives

Provided are compounds that are inhibitors of pyruvate dehydrogenase kinase (PDK), and pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition.

Development of Dihydroxyphenyl Sulfonylisoindoline Derivatives as Liver-Targeting Pyruvate Dehydrogenase Kinase Inhibitors

Pyruvate dehydrogenase kinases 1-4 (PDK1-4) negatively control activity of the pyruvate dehydrogenase complex (PDC) and are up-regulated in obesity, diabetes, heart failure, and cancer. We reported earlier two novel pan-PDK inhibitors PS8 [4-((5-hydroxyisoindolin-2-yl)sulfonyl)benzene-1,3-diol] (1) and PS10 [2-((2,4-dihydroxyphenyl)sulfonyl)isoindoline-4,6-diol] (2) that targeted the ATP-binding pocket in PDKs. Here, we developed a new generation of PDK inhibitors by extending the dihydroxyphenyl sulfonylisoindoline scaffold in 1 and 2 to the entrance region of the ATP-binding pocket in PDK2. The lead inhibitor (S)-3-amino-4-(4-((2-((2,4-dihydroxyphenyl)sulfonyl)isoindolin-5-yl)amino)piperidin-1-yl)-4-oxobutanamide (17) shows a ～8-fold lower IC50 (58 nM) than 2 (456 nM). In the crystal structure, the asparagine moiety in 17 provides additional interactions with Glu-262 from PDK2. Treatment of diet-induced obese mice with 17 resulted in significant liver-specific augmentation of PDC activity, accompanied by improved glucose tolerance and drastically reduced hepatic steatosis. These findings support 17 as a potential glucose-lowering therapeutic targeting liver for obesity and type 2 diabetes.

Industrial preparation method of 5-bromophthalide

The invention relates to a preparation method of 5-bromophthalide and mainly solves such production technical problems of an existing preparation method as expensive raw material, dangerous and complex operation, relatively low yield, high quantity of generated three wastes and etc. The technical scheme of the invention is as follows: an industrial preparation method of 5-bromophthalide is characterized in that 5-bromophthalide is obtained through three step reactions of bromination, ammoniation and reduction by taking a conventional and easily available ammoniation as a raw material. The chemical reaction formula is as shown in the description. The method provided by the invention is mainly used for industrial preparation of 5-bromophthalide.

Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: V. Synthesis of 4-bromophthalonitrile

Oxidative ammonolysis of 4-bromo-o-xylene on a V-Sb-Bi-Zr/γ-Al 2O3 catalyst gives 74.82 mol % of 4-bromophthalonitrile at a high conversion of the starting xylene in a one-cycle process. The process with recirculation results in decreased number of by-products and contribution of deep oxidation and increased selectivity in 4-bromophthalonitrile up to 95.42-96.58%.

Design, synthesis and structure-activity relationship studies of morpholino-1H-phenalene derivatives that antagonize Mcl-1/Bcl-2

We report herein characteristic studies of Mcl-1 and Bcl-2 dual inhibitors. It was found that a protruding carbonyl group forming hydrogen bond with R263 plays a predominant role compared with the hydrophobic group that occupies the p2 pocket. A series of dual inhibitors representing different parts of the morpholino-1H-phenalene were designed, synthesized and evaluated.

Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: III. Conversion of 4-bromo-o-tolunitrile as a substrate

Kinetics of oxidative ammonolysis of 4-bromo-o-tolunitrile on V-Sb-Bi-Zr/γ-Al2O3-oxide catalyst in the temperature range 633-673 K were studied. We found that the rate of conversion of 4-bromo-o-tolunitrile to the target 4-bromphthalonitrile and CO2 was described by the half-order equation with respect to the substrate concentration and was independent of the partial pressures of oxygen and ammonia. The byproducts are 4-bromophthalimide formed through the hydrolysis of 4-bromophthalonitrile, CO2 produced by oxidation of 4-bromo-o-tolunitrile and decarboxylation of 4-bromophthalimide, and 4-brombenzonitrile produced from 4-bromo-o-tolunitrile and 4-bromophthalimide.

Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: I. Transformations of 4-bromo-o-xylene and 4-bromo-o-tolunitrile

Kinetic laws of 4-bromo-phthalonitrile synthesis by vapor-phase oxidative ammonolisis of 4- bromo-o-xylene in the range of 633-69 K were studied. It was shown that formation of 4-bromophthalonitrile proceeds successively through 4-bromo-o-tolunitrile. Conversion rates of 4-bromo-o-xylene and 4-bromo-o- toluinitrile were found to be described by half-order equations on the corresponding components and not to depend on the oxygen and ammonia concentrations. Pleiades Publishing, Ltd., 2010.

Kinetics of oxidative ammonolysis of 4-bromo-o-xylene: II. Formation of by-products

Kinetic laws of formation and expenditure of by-products in the oxidative ammonolysis of 4-bromo-o-xylene in the temperature range 633-693 K were studied. It was shown that 4-bromophthalimide formation at high concentration of ammonia occurs through hydrolysis of 4-bromophthalonitrile; carbon dioxide forms by oxidation of 4-bromo-o-xylene and decarboxylation of 4-bromophthalimide; 4-bromobenzonitrile originates from 4-bromo-o-tolunitrile and 4-bromophthalimide. At low concentration of ammonia additional formation routes of 4-bromophthalimide and CO2 from 4-bromo-o-xylene are realized.