3,5-Dichlorophenylboronic Acid CAS 67492-50-6

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3,5-Dichlorophenylboronic acid exists in solid form and is usually in the form of a white crystalline powder. The molecular formula is C6H4BCl2O2, CAS67492-50-6, and the relative molecular weight is 191.81 g/mol. This compound is not easily volatile under atmospheric pressure and can be dissolved in many organic solvents, such as ethanol, acetone, dimethylformamide, tetrahydrofuran, etc. However, its solubility in water is relatively low. It is a combustible substance that may ignite when exposed to open flames or high temperature conditions.

3,5-Dichlorophenylboronic acid  is a class of aromatic boronic acid compounds with typical structure and excellent reactivity. In the molecular structure, the benzene ring is connected to two chlorine atoms at positions 3 and 5, and to a boronic acid group (- B (OH) ₂) at the para position. It combines the Suzuki coupling activity of aromatic boronic acids, the electronic effect and steric hindrance of chlorine atoms, and the reversible dimerization/esterification properties of boronic acid groups, making it an indispensable multifunctional intermediate in the fields of organic synthesis, medicine, pesticides, and materials.

(3,5-dichlorophenyl) boronic acid) is a core aromatic block in the synthesis of pharmaceutical intermediates. With its lipophilicity, metabolic stability, receptor affinity, and boronic acid coupling activity, (3,5-dichlorophenyl) boronic acid is widely used in the research and production of anti-tumor, anti infection, anti-inflammatory, hypoglycemic, cardiovascular, and neurological drugs.

 

Synthesis of anti-tumor drugs

The 3,5-dichlorophenyl structure can enhance drug lipophilicity, improve cell penetration, inhibit DNA/RNA synthesis, and target tumor enzyme receptors. It is a key side chain for various targeted drugs, chemotherapy drugs, and immune drugs.

Protein kinase inhibitors: Used as key intermediates to synthesize Bruton tyrosine kinase (BTK) inhibitors, epidermal growth factor receptor (EGFR) inhibitors, and vascular endothelial growth factor receptor (VEGFR) inhibitors.
Case: Coupling with 4-bromo-1H-pyrrolo [2,3-b] pyridine to synthesize pyrrolo pyridine BTK inhibitors for the treatment of B-cell lymphoma and chronic lymphocytic leukemia. 3,5-dichlorophenyl significantly enhances kinase selectivity, cytotoxicity, and in vivo half-life.

Proteasome inhibitors: Participate in the synthesis of bortezomib and carfizomib analogs, modify with 3,5-dichlorophenyl to enhance the inhibitory activity of drugs on the β 5 subunit of the proteasome, and increase the sensitivity of drug-resistant tumor cells.
Histone deacetylase (HDAC) inhibitor: A synthetic 3,5-dichlorophenylhydroxamic acid HDAC inhibitor is used for the treatment of solid tumors and hematological tumors, exerting its effects by regulating the epigenetics of tumor cells.
Antitumor peptide/protein modification: Used for arylation modification of peptides, antibodies, ADC drugs, 3,5-dichlorophenyl enhances peptide stability, tumor targeting, and cellular internalization efficiency.

Synthesis of anti infective drugs

 

Antibacterial drugs: intermediates for synthesizing oxazolidinones, quinolones, and sulfonamides. 3,5-dichlorophenyl enhances the bactericidal activity of drugs against Gram positive/negative bacteria and drug-resistant bacteria (MRSA, VRE) by inhibiting bacterial DNA gyrase, cell wall synthesis, and protein synthesis.
Antifungal drugs: involved in the synthesis of azole, allylamine, and echinocandin antifungal drugs. 3,5-dichlorophenyl enhances the inhibitory activity of drugs against Candida, Aspergillus, and Cryptococcus, optimizing lipid solubility and fungal cell membrane penetration.

Antiviral drugs: synthesized nucleoside and non nucleoside antiviral drug intermediates, used for the treatment of HIV, HBV, HCV, and influenza viruses. 3,5-dichlorophenyl enhances the inhibitory activity of drugs on viral reverse transcriptase and protease.

Synthesis of anti-inflammatory and immunomodulatory drugs

 

Non steroidal anti-inflammatory drug (NSAID) analogues: Synthesis of 3,5-dichlorophenyl substituted indomethacin and diclofenac analogues to enhance anti-inflammatory activity and reduce gastrointestinal irritation.

JAK kinase inhibitors: synthesized as intermediates of tofacitinib and baritinib analogues for the treatment of rheumatoid arthritis, psoriasis, and ulcerative colitis. 3,5-dichlorophenyl optimizes JAK kinase selectivity and reduces side effects.
Leukotriene inhibitors: synthetic 3,5-dichlorophenylphenoxyacetic acid leukotriene inhibitors used for the treatment of asthma and allergic rhinitis.

Metabolic diseases and cardiovascular drug synthesis

 

Hypoglycemic drugs: Participate in the synthesis of insulin sensitizers, dipeptidyl peptidase 4 (DPP-4) inhibitors, and SGLT2 inhibitors.
Case: 12- (3,5-dichlorophenyl) berberine was synthesized by Suzuki coupling with 12 bromoberberine, which has significant insulin sensitizing activity and is used for the treatment of type 2 diabetes.

Lipid lowering drugs: Synthesize 3,5-dichlorophenyl substituted statin and beta drug analogues to enhance cholesterol and triglyceride regulatory activity.
Antihypertensive drugs: Participate in the synthesis of angiotensin receptor antagonists (ARBs) and calcium channel blockers, optimize receptor affinity, antihypertensive effect, and pharmacokinetics with 3,5-dichlorophenyl.

This section mainly refers to sources:

1. MedChemExpress. 3,5-Dichlorophenylboronic Acid in Pharmaceutical Intermediate Synthesis. 2026.
2. X technology patent. Preparation method of berberine 12 derivative with insulin sensitizing activity two thousand and twenty-two
3. The BioTek. 3,5-Dichlorophenylboronic Acid as a Key Building Block for Anticancer and Anti-Infective Drugs. 2023.
4. Huayuan Network Research on the application of 3,5-dichlorophenylboronic acid as a pharmaceutical intermediate two thousand and twenty-five
5. MolBase. 3, Application of 5-dichlorophenylboronic acid in the synthesis of metabolic disease drugs two thousand and twenty-three

3,5-dichlorophenylboronic acid is a key intermediate for the synthesis of green and efficient pesticides. The 3,5-dichlorophenyl structure endows pesticides with high insecticidal/bactericidal/herbicidal activity, strong systemic absorption, good environmental compatibility, and low crop toxicity. It is widely used in the research and development of insecticides, fungicides, herbicides, and plant growth regulators.

Insecticide synthesis

 

Isoxazoline insecticides: 3,5-dichlorophenylboronic acid is the core raw material of the new isoxazoline insecticides. This type of insecticide efficiently kills pests such as fruit flies, corn borers, aphids, planthoppers, and Lepidoptera larvae by blocking GABA and glutamate gated chloride ion channels in insects. It is low toxicity, efficient, and environmentally friendly.

Case: Using 3,5-dichlorophenylboronic acid and 5-bromo-3-methyl-2-pyridinecarboxylic acid methyl ester as raw materials, G4 isoxazoline compound was synthesized through 7 steps of reaction. At a concentration of 100 mg/L, the mortality rate of fruit flies and corn borers reached 100%, and the activity was superior to existing commercially available varieties.

Imidacloprid insecticides: used for the synthesis of fluorocyhalothrin and bromocyhalothrin analogues, with 3,5-dichlorophenyl enhancing insecticidal activity, shelf life, and photostability.
New nicotine insecticides: modify the structure of imidacloprid and thiamethoxam to enhance the killing effect on piercing sucking mouthparts pests and reduce bee toxicity.

Synthesis of fungicides

Triazole/pyrimidine fungicides: synthetic 3,5-dichlorophenyl substituted triazole alcohol and pyrimidine amine fungicides are used to prevent and control wheat powdery mildew, rice blast disease, cucumber downy mildew, and apple scab. They have protective, therapeutic, and eradication effects, strong internal absorption conductivity, and a wide antibacterial spectrum.

Methoxyacrylate fungicides: used as intermediates to synthesize pyraclostrobin and pyraclostrobin analogues, they exert their effects by inhibiting fungal mitochondrial respiration and are highly effective against oomycetes, ascomycetes, and basidiomycetes.

Herbicides and plant growth regulators

Herbicide: synthetic 3,5-dichlorophenylphenoxyacetic acid and pyrimidinoxybenzoic acid herbicides, used for controlling grasses and broad-leaved weeds, with high selectivity and crop safety.

Plant growth regulator: 3,5-dichlorophenyl jasmonic acid and cytokinin analogues are synthesized through derivatization to promote plant growth, flower bud differentiation, fruit enlargement, and enhance stress resistance. They are used for increasing yield in wheat, rice, vegetables, and fruit trees.

This section mainly refers to sources

1. Gaide Chemical Network Application of 3,5-dichlorophenylboronic acid in the synthesis of insecticides and fungicides two thousand and twenty-four
2. Huayuan Network Instructions for the use of 3,5-dichlorophenylboronic acid as an intermediate in agricultural chemicals two thousand and twenty-five
3. MolBase. 3, Research on the synthesis route and activity of 5-dichlorophenylboronic acid pesticide two thousand and twenty-three
4. ChemicalBook. 3, Market and application prospects of 5-dichlorophenylboronic acid pesticide intermediate two thousand and twenty-six

 

Liquid Crystal and Organic Optoelectronic Materials

3,5-dichlorophenylboronic acid is a key intermediate for high-performance liquid crystal materials, organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic solar cells (OSCs).
Liquid Crystal Materials: Synthesize 3,5-dichlorophenylbiphenyl and 3,5-dichlorophenylcyclohexane liquid crystal monomers to enhance the dielectric anisotropy, thermal stability, low-temperature flowability, and response speed of liquid crystals, suitable for LCD and OLED displays.

OLED materials: As intermediates for the luminescent and transport layers, 3,5-dichlorophenyl substituted carbazole, triphenylamine, and fluorene derivatives are synthesized to improve OLED efficiency, lifespan, and color purity.
Organic semiconductor materials: used for the synthesis of conjugated polymers and small molecule semiconductors. 3,5-dichlorophenyl regulates molecular aggregation states, enhances carrier mobility, and stability.

Polymer Materials and Functional Polymers

 

Polyborate esters and polyarylethers: condensed with diols and diphenols to synthesize polyborate esters and polyarylethers, used in biodegradable materials, drug carriers, separation membranes, and high-temperature resistant coatings.
Flame retardant material: 3,5-dichlorophenylboronic acid is used as a flame retardant monomer and flame retardant synergist for flame retardant modification of epoxy resin, polypropylene, and polyester, improving the flame retardant grade, smoke suppression, and mechanical properties of the material.

Surface functionalized materials: modify the surfaces of silica, graphene, quantum dots, and magnetic nanoparticles through boronic acid esterification reaction for biological separation, catalysis, sensing, and targeted delivery.

Biosensing and Diagnostic Reagents

 

Sugar/nucleoside sensor: as a recognition element, it is used to prepare fluorescent, electrochemical and colorimetric sensors to detect glucose, fructose, ribose and nucleoside with high sensitivity and selectivity for diabetes diagnosis, food detection and biomedical research.
Enzyme activity probe: Synthesize 3,5-dichlorophenylboronic acid ester probes for real-time detection of protease, glycosidase, and phosphatase activities, used for drug screening and disease diagnosis.
Protein labeling reagents: specifically label glycosides of glycoproteins and antibodies, used for proteomics, immunoassay, and biological imaging.

Analytical reagents and standards

 

Chromatographic analysis: As a derivatization reagent, it is used for GC-MS and HPLC analysis of diols, hydroxy acids, and sugars to improve detection sensitivity and separation.
Standard and reference materials: High purity 3,5-dichlorophenylboronic acid is used as a standard, internal standard, and reference material for drugs, pesticides, and environmental monitoring.

This section mainly refers to sources

1. Fisher Scientific. 3,5-Dichlorophenylboronic Acid in Liquid Crystal and Optoelectronic Materials. 2026.
2. MolBase. 3, Application of 5-dichlorophenylboronic acid in polymer materials and biosensing two thousand and twenty-three
3. The BioTek. Arylboronic Acids for Advanced Materials and Biosensing Applications. 2023.
4. Huayuan Network Application of 3,5-dichlorophenylboronic acid material science and analytical reagent two thousand and twenty-five

3,5-Dichlorophenylboronic acid (DCPB), as a boron containing aromatic compound, has shown extensive potential in the field of life sciences due to its unique chemical structure (the 3rd and 5th positions of the benzene ring are replaced by chlorine atoms, and the boronic acid group provides reactivity). From serine proteases that catalyze protein hydrolysis to carbohydrate binding proteins that recognize carbohydrate molecules, DCPB is deeply involved in key biological processes such as enzyme activity regulation, protein interactions, and glucose metabolism signal transduction through covalent modification, non covalent binding, and structural simulation mechanisms.

Structure and Function of Serine Proteases

Serine proteases are a family of enzymes that rely on active center serine residues (Ser) to catalyze peptide bond hydrolysis, and are widely involved in physiological processes such as digestion, coagulation, and immune response. Its typical structure includes a catalytic triad (Ser His Asp), in which the hydroxyl group of Ser acts as a nucleophile to attack the carbonyl carbon of the substrate peptide bond, forming a covalent acyl enzyme intermediate, which is then hydrolyzed to complete the catalytic cycle.

Covalent modification of serine protease by DCPB

DCPB can covalently bind to the Ser hydroxyl group in the active center of serine protease through boronic acid groups, forming boronic ester bonds and inhibiting enzyme activity. For example, in trypsin, DCPB modification leads to a significant decrease in the enzyme's ability to hydrolyze substrates such as arginine or lysine carboxyl terminal peptide bonds, with IC ₅₀ values reaching micromolar levels. This inhibitory effect is reversible, and enzyme activity can be restored by adding excessive competitive substrates or adjusting pH, providing new ideas for designing controllable enzyme inhibitors.

The effect of DCPB on enzyme conformation and dynamics

In addition to direct covalent modification, DCPB can also affect the conformational stability of enzymes through non covalent interactions such as hydrophobic interactions and hydrogen bonding. Molecular dynamics simulations show that after DCPB binding, there is a slight shift in the spatial arrangement of the catalytic triad of trypsin, leading to a decrease in the proton transfer efficiency of His and thus weakening the catalytic activity. In addition, the chlorine substituent of DCPB can be embedded into the hydrophobic pocket of the enzyme, stabilizing the inactive conformation of the enzyme and forming a long-lasting inhibitory effect.

Application Case: Development of Thrombin Inhibitors

Thrombin is a key serine protease that plays a central role in thrombus formation. Based on the boronic ester formation characteristics of DCPB, researchers have designed a series of thrombin inhibitors, among which representative compounds have shown significant antithrombotic effects in animal models and have lower bleeding side effects than traditional heparin drugs. This achievement provides a new candidate drug for the treatment of cardiovascular diseases.

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