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2-bromobenzene-1,3-dicarboxylic acid, also known as bibenzylidene, is a chemical compound with the molecular formula C10H7BrO4. It is a benzene derivative that features two carboxylic acid groups and a bromine atom, making it a versatile building block in the synthesis of pharmaceuticals, fine chemicals, dyes, pigments, and advanced materials.

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  • 22433-91-6 Structure
  • Basic information

    1. Product Name: 2-bromobenzene-1,3-dicarboxylic acid
    2. Synonyms: 2-bromobenzene-1,3-dicarboxylic acid;1,3-Benzenedicarboxylicacid, 2-bromo-
    3. CAS NO:22433-91-6
    4. Molecular Formula: C8H5BrO4
    5. Molecular Weight: 245.03
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 22433-91-6.mol
  • Chemical Properties

    1. Melting Point: 218 °C
    2. Boiling Point: 427°Cat760mmHg
    3. Flash Point: 212°C
    4. Appearance: /
    5. Density: 1.875g/cm3
    6. Vapor Pressure: 4.74E-08mmHg at 25°C
    7. Refractive Index: 1.652
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 2.18±0.10(Predicted)
    11. CAS DataBase Reference: 2-bromobenzene-1,3-dicarboxylic acid(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2-bromobenzene-1,3-dicarboxylic acid(22433-91-6)
    13. EPA Substance Registry System: 2-bromobenzene-1,3-dicarboxylic acid(22433-91-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22433-91-6(Hazardous Substances Data)

22433-91-6 Usage

Uses

Used in Organic Synthesis:
2-bromobenzene-1,3-dicarboxylic acid is used as a key intermediate in the synthesis of various organic compounds due to its reactive bromine atom and carboxylic acid groups, which can be easily modified in chemical reactions.
Used in Pharmaceutical Production:
As a building block, 2-bromobenzene-1,3-dicarboxylic acid is utilized in the production of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Fine Chemicals Industry:
2-bromobenzene-1,3-dicarboxylic acid serves as a precursor in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including fragrances, flavors, and agrochemicals.
Used in Dye and Pigment Preparation:
2-bromobenzene-1,3-dicarboxylic acid is used as a precursor in the preparation of dyes and pigments, which are essential for coloring textiles, plastics, and other materials.
Used in Materials Science:
In the field of materials science, 2-bromobenzene-1,3-dicarboxylic acid has potential applications in the development of polymers and advanced materials, such as high-performance plastics and composites, due to its unique chemical structure and properties.

Check Digit Verification of cas no

The CAS Registry Mumber 22433-91-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,4,3 and 3 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 22433-91:
(7*2)+(6*2)+(5*4)+(4*3)+(3*3)+(2*9)+(1*1)=86
86 % 10 = 6
So 22433-91-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H5BrO4/c9-6-4(7(10)11)2-1-3-5(6)8(12)13/h1-3H,(H,10,11)(H,12,13)

22433-91-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-bromobenzene-1,3-dicarboxylic acid

1.2 Other means of identification

Product number -
Other names bromo-isophthalic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22433-91-6 SDS

22433-91-6Relevant articles and documents

Fully bridged triphenylamine derivatives as color-tunable thermally activated delayed fluorescence emitters

Zou, Sheng-Nan,Peng, Chen-Chen,Yang, Sheng-Yi,Qu, Yang-Kun,Yu, You-Jun,Chen, Xing,Jiang, Zuo-Quan,Liao, Liang-Sheng

, p. 958 - 962 (2021)

Three emissive bridged-triphenylamine derivatives are designed and synthesized by incorporating carbon (DQAO), oxygen (OQAO), and sulfur (SQAO) atoms with two carbonyl groups. The fully bridged geometry and unique frontier molecular orbital distribution r

Structure-based design of novel naproxen derivatives targeting monomeric nucleoprotein of Influenza A virus

Tarus, Bogdan,Bertrand, Hélène,Zedda, Gloria,Di Primo, Carmelo,Quideau, Stéphane,Slama-Schwok, Anny

, p. 1899 - 1912 (2015)

The nucleoprotein (NP) binds the viral RNA genome as oligomers assembled with the polymerase in a ribonucleoprotein complex required for transcription and replication of influenza A virus. Novel antiviral candidates targeting the nucleoprotein either induced higher order oligomers or reduced NP oligomerization by targeting the oligomerization loop and blocking its insertion into adjacent nucleoprotein subunit. In this study, we used a different structure-based approach to stabilize monomers of the nucleoprotein by drugs binding in its RNA-binding groove. We recently identified naproxen as a drug competing with RNA binding to NP with antiinflammatory and antiviral effects against influenza A virus. Here, we designed novel derivatives of naproxen by fragment extension for improved binding to NP. Molecular dynamics simulations suggested that among these derivatives, naproxen A and C0 were most promising. Their chemical synthesis is described. Both derivatives markedly stabilized NP monomer against thermal denaturation. Naproxen C0 bound tighter to NP than naproxen at a binding site predicted by MD simulations and shown by competition experiments using wt NP or single-point mutants as determined by surface plasmon resonance. MD simulations suggested that impeded oligomerization and stabilization of monomeric NP is likely to be achieved by drugs binding in the RNA grove and inducing close to their binding site conformational changes of key residues hosting the oligomerization loop as observed for the naproxen derivatives. Naproxen C0 is a potential antiviral candidate blocking influenza nucleoprotein function.

Complexes and Ligands

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Page/Page column 0612-0613; 0616-0617, (2022/02/05)

The present application provides ligands and fluorescent or luminescent complexes comprising these ligands.

Electrochemical Generation of Hypervalent Bromine(III) Compounds

Francke, Robert,Mohebbati, Nayereh,Sokolovs, Igors,Suna, Edgars

supporting information, p. 15832 - 15837 (2021/06/14)

In sharp contrast to hypervalent iodine(III) compounds, the isoelectronic bromine(III) counterparts have been little studied to date. This knowledge gap is mainly attributed to the difficult-to-control reactivity of λ3-bromanes as well as to their challenging preparation from the highly toxic and corrosive BrF3 precursor. In this context, we present a straightforward and scalable approach to chelation-stabilized λ3-bromanes by anodic oxidation of parent aryl bromides possessing two coordinating hexafluoro-2-hydroxypropanyl substituents. A series of para-substituted λ3-bromanes with remarkably high redox potentials spanning a range from 1.86 V to 2.60 V vs. Ag/AgNO3 was synthesized by the electrochemical method. We demonstrate that the intrinsic reactivity of the bench-stable bromine(III) species can be unlocked by addition of a Lewis or a Br?nsted acid. The synthetic utility of the λ3-bromane activation is exemplified by oxidative C?C, C?N, and C?O bond forming reactions.

Catalytic Activation of N2O at a Low-Valent Bismuth Redox Platform

Pang, Yue,Leutzsch, Markus,N?thling, Nils,Cornella, Josep

supporting information, p. 19473 - 19479 (2020/12/01)

Herein we present the catalytic activation of N2O at a BiI→BiIII redox platform. The activation of such a kinetically inert molecule was achieved by the use of bismuthinidene catalysts, aided by HBpin as reducing agent. The protocol features remarkably mild conditions (25 °C, 1 bar N2O), together with high turnover numbers (TON, up to 6700) and turnover frequencies (TOF). Analysis of the elementary steps enabled structural characterization of catalytically relevant intermediates after O-insertion, namely a rare arylbismuth oxo dimer and a unique monomeric arylbismuth hydroxide. This protocol represents a distinctive example of a main-group redox cycling for the catalytic activation of N2O.

A NEW TYPE OF ANTITUMOR COMPOUNDS: DERIVATIVES OF 7-PROPANAMIDE SUBSTITUTED BENZOXABOROLE

-

Page/Page column 3, (2020/10/09)

The present disclosure relates to derivatives of 7-propanamide substituted benzoxaborole and their preparation and use. The structural general formula of the derivatives is (formula).The derivatives are used for the preparation of a medicament for the pre

CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR MODULATING AGENTS

-

Paragraph 00210, (2020/10/20)

Compound (I), deuterated derivatives, and pharmaceutically acceptable salts of any of the foregoing are disclosed. Methods of treating cystic fibrosis using these compounds are also disclosed.

A Molecular Torsion Balance Study: A Nearby Anionic Group Exerts Little Influence on Hydrophobic Interactions between Nonpolar Surfaces

Ling, Xiujun,Wilcox, Craig S.

supporting information, p. 14010 - 14014 (2019/11/14)

Polar groups have a solvent ordering effect on water and therefore may affect hydrophobic binding energies for nearby lipophilic surfaces. This would mean that determinations of excess surface free energy association energies require consideration of nearby polar functional groups. This paper reports results of a study to measure this possible effect. It was concluded from the models used here that an anionic polar group nearby a hydrophobic surface has little or no effect on the magnitude of hydrophobic association.

DERIVATIVES OF 7-FATTY ACID SUBSTITUTED BENZOXABOROLE AND THEIR PREPARATION AND USE

-

Page/Page column 5-6, (2019/08/29)

The present disclosure relates to derivatives of 7-fatty acid substituted benzoxaborole and their preparation and use. The structural general formula of the derivatives is (I). The derivatives are used for the preparation of a medicament for the preventio

Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents

Zhang, Jiong,Zhang, Jinyi,Hao, Guiyun,Xin, Weixiang,Yang, Fei,Zhu, Mingyan,Zhou, Huchen

, p. 6765 - 6784 (2019/08/20)

Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.

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