610-71-9

Basic information

• Product Name: 2,5-Dibromobenzoic acid
• Synonyms: 2,5-dibromo-benzoicaci;Benzoic acid, 2,5-dibromo-;2,5-DIBROMOBENZOIC ACID;2,5-Dibromobenzoicacid,95%;5-DibroMobenzoic acid;2,5-DibroMobenyoic, Acid;2,5- twobroMo benzoic acid
• CAS NO: 610-71-9
• Molecular Formula: C₇H₄Br₂O₂
• Molecular Weight: 279.91
• EINECS: 210-234-7
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Acids & Esters;Bromine Compounds;C7;Carbonyl Compounds;Carboxylic Acids
• Mol File: 610-71-9.mol

Chemical Properties

• Melting Point: 156-159 °C(lit.)
• Boiling Point: 344.6 °C at 760 mmHg
• Flash Point: 162.2 °C
• Appearance: /
• Density: 1.9661 (rough estimate)
• Vapor Pressure: 2.48E-05mmHg at 25°C
• Refractive Index: 1.4970 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 2.46±0.10(Predicted)
• BRN: 1868193
• CAS DataBase Reference: 2,5-Dibromobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dibromobenzoic acid(610-71-9)
• EPA Substance Registry System: 2,5-Dibromobenzoic acid(610-71-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DG6290000
• Hazardous Substances Data: 610-71-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dibromobenzoic acid is used as an intermediate for the preparation of benzo[c]chromenone and benzo[c]chromene derivatives. These derivatives serve as estrogen β-receptor-selective agonists, which are crucial in the development of treatments for conditions related to estrogen levels, such as menopause and osteoporosis. The comparison with effusol and estradiol highlights its potential effectiveness in this application.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,5-dibromobenzoic acid is utilized in the synthesis of aminopyridine-based c-Jun N-terminal kinase (JNK) inhibitors. These inhibitors possess cellular activity and exhibit minimal cross-kinase activity, making them valuable in the development of targeted therapies for various diseases, including cancer and neurodegenerative disorders.
Overall, 2,5-dibromobenzoic acid plays a significant role in the pharmaceutical and chemical synthesis industries due to its unique chemical properties and its ability to be used in the creation of important compounds and therapeutic agents.

Purification Methods

Crystallise the acid from water or EtOH. [Beilstein 9 H 358, 9 I 147, 9 II 237, 9 III 1428, 9 IV 1027.]

InChI:InChI=1/C7H4Br2O2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11)/p-1

Upstream product

• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 29798-82-1 2,4,7-tribromotropone 
• 615-59-8 1,4-dibromo-2-methylbenzene 
• 552-16-9 ortho-nitrobenzoic acid 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 151-50-8 potassium cyanide 
• 32937-55-6 1-(2,5-dibromophenyl)ethanone 
• 57381-41-6 2,5-dibromophenyl cyanide 
• 2840-02-0 5-acetamido-2-bromobenzoic acid 
• 861602-70-2 4-amino-2,5-dibromo-benzoic acid 
• 65-85-0 benzoic acid 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 

Downstream Products

• 59615-13-3 2,5-Dibromobenzoic acid chloride 
• 76008-76-9 2,5-dibromobenzoic acid ethyl ester 
• 87976-27-0 benzoic-2,5-d2 acid 
• 585-76-2 m-bromobenzoic acid 
• 65-85-0 benzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 82762-60-5 N-phenyl-5-bromoanthranilic acid 
• 57381-43-8 2,5-dibromobenzoic acid methyl ester 
• 60573-67-3 2-Brom-5-(1-cyclohexenyl)benzoesaeure 
• 207804-89-5 2-(4-bromo-2-carboxyphenyl)malonic acid dimethyl ester 
• 222021-56-9 5-bromo-2-(2-dimethylcarbamoyl-phenylsulfanyl)-benzoic acid 
• 124-38-9 carbon dioxide 
• 106-37-6 1.4-dibromobenzene 
• 546109-92-6 11-hydroxyundecyl 2,5-dibromobenzoate 

Relevant articles and documents

Copolyphenylenes with pendant benzimidazolyl and diethanolaminohexyloxy groups: Synthesis and electron-transporting application in PLEDs

Two new electron-transporting copolyphenylenes P1NH and P2NH possessing balanced charges crucial to emission efficiency of polymer light-emitting diodes (PLEDs) have been synthesized and applied as an electron-transporting layer (ETL). The main chain structure is all para-linkage for P1NH and both para- and meta-linkage for P2NH, with the same pendant electron-withdrawing benzimidazolyl and polar diethanolaminohexyloxy groups. Both copolymers possess excellent thermal stability (Td > 300 °C, Tg > 100 °C) due to their rigid backbones. In addition, the pendant groups effectively lower LUMO (～ ?2.70 eV) and HOMO (～ ?5.70 eV) levels, resulting in improved electron-transporting and hole-blocking capabilities. Multilayer yellow-emitting PLEDs with a configuration of ITO/PEDOT:PSS/SY/ETL/LiF/Al were successfully fabricated by the spin-coating process. The maximum luminance and maximum current efficiency of the P1NH-based device were 12,881 cd/m2 and 10.94 cd/A, respectively, superior to the performance of P2NH-based device (4938 cd/m2, 3.70 cd/A) and the device without ETL (8690 cd/m2, 2.78 cd/A). Current results indicate that P1NH is highly effective in enhancing electron transport and device performance.

Tandem copper catalyzed regioselectiveN-arylation-amidation: synthesis of angularly fused dihydroimidazoquinazolinones and the anticancer agent TIC10/ONC201

Herein, we present a copper-catalyzed tandem reaction of 2-aminoimidazolines andortho-halo(hetero)aryl carboxylic acids that causes the regioselective formation of angularly fused tricyclic 1,2-dihydroimidazo[1,2-a]quinazolin-5(4H)-one derivatives. The reaction involved in the construction of the core six-membered pyrimidone moiety proceededviaregioselectiveN-arylation-condensation. The presented protocol been successfully applied to accomplish the total synthesis of TIC10/ONC201, which is an active angular isomer acting as a tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL): a sought after anticancer clinical agent.

Synthesis method of 2-halo-5-bromobenzoic acid

The invention discloses a synthesis method of 2-halo-5-bromobenzoic acid. The method comprises the following steps of under the action of sulfuric acid, carrying out a bromination reaction on o-halo-benzoic acid and NBS in an organic solvent, and after the reaction is finished, carrying out posttreatment to obtain 2-halo-5-bromobenzoic acid. The method has the advantages of being short in reactionroute, simple in operation, environmentally friendly, safe and economical and has a broad application prospect.

Preparation method of 2,5-dihalo-benzoic acid

The invention discloses a preparation method of 2,5-dihalo-benzoic acid. The method comprises the following steps: concentrated sulfuric acid is added dropwise to a mixed solution containing sodium bromide, periodate and 2-halo-benzoic acid in presence of water and acetic acid, the mixed solution is subjected to a reaction, and 2,5-dihalo-benzoic acid is prepared. The problems of long time neededfor preparation, high reaction temperature and the like of the preparation method of 2,5-dihalo-benzoic acid in the prior art can be solved.

Substitution effect on the regioselective halogen/metal exchange of 3-substituted 1,2,5-tribromobenzenes

Regioselective halogen/metal exchange reactions using isopropylmagnesium chloride were studied on 3-substituted 1,2,5-tribromoarenes. Seven examples are given.

Regioselective generation of aryllithiums from substituted bromobenzenes XC6H4Br (X = 4-Br, 4-I, 4-CN, 2-CN)

Selected activated bromobenzenes XC6H4Br (X = 4-Br, 4-I, 4-CN, 2-CN) were successfully deprotonated with lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF at -80°C. Thus, 2,5-dibromo-, 2-bromo-5-iodo-, 5-bromo-2-cyano-, and 3-bromo

Use of Potassium Bromate: Bromination of Halobenzenes and Halobenzoic Acids

Syntheses of bromo compounds by the bromination of halobenzenes and halobenzoic acids using potassium bromate under acidic condition have been discussed.