4,4'-Dimethylbiphenyl CAS 613-33-2

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4,4'-Dimethylbiphenyl, CAS No. 613-33-2, white crystal. Almost insoluble in water, easily soluble in organic solvents such as ethanol, acetone, dimethylformamide, etc. It is a molecule containing two benzene rings and two methyl groups, so it has a higher melting point and boiling point. It is slightly denser than water, insoluble in water, but soluble in many organi solvents. It can be used as a plasticizer, preservative, and also used in the manufacture of dyes, engineering plastics, high-energy fuels, and the intermediate 4-phenylbenzophenone of antifungal drugs, etc.

4,4'- dimethylbiphenyl (CAS number: 613-33-2), chemical formula C14H14, is a white to pale yellow crystalline powder with high thermal stability, low vapor pressure, and good solubility. The two methyl groups in its molecular structure are symmetrically distributed at positions 4 and 4 'of the biphenyl skeleton, endowing it with unique physical and chemical properties, making it widely applicable in various fields such as chemical engineering, medicine, material, agriculture, etc. The following provides a systematic analysis of the six core areas:

Chemical industry: Core components of solvents and heat transfer media

 

1. High boiling point solvents
The boiling point is as high as 295 ° C, with a melting point of 118-120 ° C, making it an ideal solvent for high-temperatur riposte systems. For example, in organi synthesis, it can be used to dissolve high molecular weight polymers or participate in condensation ripostes under high temperatur conditions, avoiding fluctuations in riposte conditions caused by solvent evaporation. Its low vapor pressure characteristic also reduces solvent loss during operation and improves riposte efficiency.

2. Heat carrier and heat transfer agent
Due to its high thermal stability, it is often used alone or mixed with diphenyl ether to make thermal oil, which is widely used in heating and cooling systems in chemical production.

 

For example, in high-temperatur processes such as petroleum refining and chemical fiber 4,4'-dimethylbiphenyl, this mixture can stably transfer heat within the range of -40 ° C to 400 ° C, and is not easily decomposed or corroded by equipment, significantly extending the system's service life.

3. Fruit mold inhibitor
Antibacterial properties make it an impregnating agent for citrus and other fruit packaging paper. It effectively inhibits mold growth and prolongs fruit preservation by disrupting the structure of microbial cell membranes. Experiments have shown that processed citrus fruits can extend their storage period by 7-10 days at room temperatur and reduce decay rates by over 40%.

Pharmaceutical field: key raw materials for intermediates and drug synthesis

 

1. Pharmaceutical intermediates
It is an important precursor for synthesizing multiple drugs. For example, its derivative 4-phenylbenzophenone can be used to prepare antifungal drugs by inhibiting the synthesis of ergosterol on fungal cell membranes, achieving efficient killing of pathogens such as dermatophytes and yeast. In addition, it can also be used to synthesize anti-inflammatory drugs, anti-tumor drugs, etc., exerting therapeutic effects by regulating cell signaling pathways or inducing tumor cell apoptosis.2. Drug carriers and sustained-release materials
By utilizing the hydrophobicity of 4,4 '- dimethylbiphenyl, it can be blended with hydrophilic polymers to prepare nanoparticles or microspheres for targeted delivery and sustained release of drugs.

 

For example, adding PLGA nanoparticles synthesized using soy peptone as a template can significantly improve drug encapsulation efficiency and prolong drug circulation time in vivo to over 72 hours.

3. Dyeing carrier and color developer
In the field of pharmaceutical testing, its derivative p-phenylphenol is the core color developer for pressure-sensitive copy paper. It achieves rapid development of text or images through acid-base ripostes with colorless dyes, and is widely used in scenarios such as medical bills and inspection reports.

Materials Science: Polymer Modification and Functional Additives

 

1. Modification of engineering plastics
It can be used as a plasticizer for engineering plastics such as polycarbonate (PC) and polyamide (PA), improving the flexibility and processability of materials by reducing intermolecular forces. For example, adding 2% 4,4 '- dimethylbiphenyl to PC can increase the material's elongation at break by 30% while maintaining its high transparency and heat resistance.

2. LCD display materials
As a key component of liquid crystal mixtures, the phase transition temperatur and dielectric constant of the liquid crystal can be adjusted to optimize display performance.

 

For example, in twisted nematic (TN) liquid crystals, the liquid crystal alignment is stabilized through intermolecular π - π interactions, resulting in a contrast ratio of over 1000:1 and a response time of less than 10ms.

3. Photosensitive materials and flame retardants
4,4'-Dimethylbiphenyl derivatives such as ethylbiphenyl and diethylbiphenyl can be used as crosslinking agents for photosensitive resins, which can achieve high-precision 3D printing or photolithography patterns through UV induced polymerization ripostes. In addition, its bromine derivatives can also be used as flame retardants for the fire protection treatment of materials such as epoxy resin and polyurethane, achieving a flame retardant rating of UL94 V-0 standard.

Agricultural field: pesticide synthesis and plant protection

 

1. Pesticide intermediates
It is a key raw material for synthesizing pyrethroid insecticides. For example, 4,4 '- dibromomethylbiphenyl prepared by bromination riposte can be further synthesized into highly efficient insecticides such as cypermethrin and deltamethrin, which have dual effects of contact and stomach toxicity on agricultural pests such as cotton bollworms and aphids, with a mortality rate of over 95%.

2. Plant disease treatment agents
Its antibacterial properties make it suitable for disease control in citrus plants.

 

For example, by inhibiting the spore germination and hyphal growth of pathogenic bacteria, it effectively controls the occurrence of common diseases such as ulcer disease and anthrax, and increases the fruit commodity rate by 20% -30%.

3. Soil amendments
As an organi carbon source, it can promote the reproduction and activity of soil microorganisms, and improve soil structure. Experiments have shown that adding 0.1% 4,4 '- dimethylbiphenyl to acidic soil can increase soil pH by 0.5-1.0 units, while improving the effectiveness of nutrients such as nitrogen and phosphorus, and promoting crop growth.

Environmental Protection Field: Pollution Control and Resource Recycling

 

1. Heavy metal adsorbent
The sulfur-containing derivatives of 4,4 '- dimethylbiphenyl have high selective adsorption capacity for heavy metal ions such as Pb ² ⁺ and Cd ² ⁺. For example, the composite material of modified soy peptone and 4,4 '- dimethylbiphenyl has an adsorption capacity of up to 120mg/g for Pb ² ⁺, which is much higher than that of activated carbon (50mg/g), and the adsorbent can be regenerated and recycled through acid washing.

2. Oil pollution remediation
In microbial remediation technology, adding 0.1% 4,4 '- dimethylbiphenyl to the culture medium can increase the degradation rate of Pseudomonas aeruginosa on crude oil by 40%.

 

It provides carbon sources and energy for microorganisms, promotes the synthesis and activity of degradation enzymes, and accelerates the mineralization process of petroleum hydrocarbons.

3. Wastewater treatment
Its oxidation products can be used as coagulants for the treatment of industrial wastewater such as printing and dyeing wastewater and electroplating wastewater. For example, through charge neutralization and bridging, suspended solids and heavy metal ions in wastewater are rapidly settled, achieving a COD removal rate of over 80% and meeting national discharge standards.

4,4'-Dimethylbiphenyl is a significant organic compound with diverse applications across various fields, including materials science, pharmaceuticals, organic synthesis, and research and development. Its unique structure, characterized by two benzene rings connected by a single bond with methyl groups at the 4-positions, gives it distinct physical and chemical properties that make it valuable for different purposes. The synthesis of 4,4'-dimethylbiphenyl can be achieved through various methods, with coupling reactions being the most common. Understanding its properties, applications, and safety considerations is essential for its effective and safe use in industrial and academic settings. As research continues to advance, new applications and safer handling methods for 4,4'-dimethylbiphenyl may emerge, further expanding its utility and ensuring its sustainable use in the future.

To a screw cap vial with a stir bar was added 4-bromotoluene (86.4 mg, 0.5 mmol), phenyltrimethoxysilane (152 mg, 0.75 mmol), PS PdONPs (2.9 mg, 1.5 mol%Pd), TBAC ( 142 mg, 0.5 mmol) and aq NaOH solution (1.5 M, 1 mL). After stirring at 80 °C for 3 h, the vial was immediately immersed in H2O (~20 °C) for about 10 min and the riposte mixture was cooled to r.t. After separating the catalyst and the aqueous phase by centrifugation, the aqueous phase was decanted. Wash the recovered catalyst with H2O (5 x 3.0 mL) and Et2O (5 x 3.0 mL), then add it to the aqueous phase. The aqueous phase was extracted eight times with Et2O. The combined organi extracts were dried over MgSO4 and concentrated under reduced pressure to give the product 4,4'-dimethylbiphenyl. The product was analyzed by 1H NMR.

To a screw cap vial with a stir bar was added 4-bromotoluene (86.4 mg, 0.5 mmol), phenyltrimethoxysilane (152 mg, 0.75 mmol), PS PdONPs (2.9 mg, 1.5 mol%Pd), TBAC ( 142 mg, 0.5 mmol) and aq NaOH solution (1.5 M, 1 mL). After stirring at 80 °C for 3 h, the vial was immediately immersed in H2O (~20 °C) for about 10 min and the riposte mixture was cooled to r.t. After separating the catalyst and the aqueous phase by centrifugation, the aqueous phase was decanted. Wash the recovered catalyst with H2O (5 x 3.0 mL) and Et2O (5 x 3.0 mL), then add it to the aqueous phase. The aqueous phase was extracted eight times with Et2O. The combined organi extracts were dried over MgSO4 and concentrated under reduced pressure. The product was analyzed by 1H NMR. And ICP-AES analysis and determination of product. The NMR data are as follows: 1H NMR (CDCl3): δ=7.55-7.60 (m, 2H), 7.47-7.50. 13C NMR (CDCl3): δ=141.1, 138.3, 136.9, 129.4, 128.7, 128.7126.9, 21.1.

A solution of picolinic acid rac-8 (54.9 mg, 0.201 mmol) in THF (1 mL) was added to bromobenzene (101 mg, 0.643 mmol) in EtO (1 mL) at -40°C, t -BuLi (1.77 M in pentane, 0.670 mL, 1.19 mmol), CuTC (60.8 mg, 0.319 mmol) and MgBr2 OEt2 (0.20 M in THF-, 6.40 mL, 1.28 mmol), and the mixture was allowed to Warm to -20°C over 2 hours. A mixture of rac-9a and Ph2 in a ratio of 87:13 (45.1 mg in total, 89% yield of rac-9a) was obtained as a colorless oil by 1H NMR analysis. By 1H NMR spectroscopy, gamma/α=99:1. The 1H NMR spectrum of the product is consistent with the above results. (E)-1-(4,8-Dimethylnon-2,7-dien-4-yl)-4-toluene (rac-9b) was heated at -40 °C according to the general procedure via Method B A solution of picolinic acid rac-8 (54.9 mg, 0.201 mmol) in THF (1 mL) was added to 4-iodotoluene (139 mg, 0.639 mmol), t-BuLi (1.77 M in pentane, 0.670 mL, 1.19 mmol degrees Celsius, and by 1H NMR analysis, the mixture was allowed to warm to -20°C over 2 hours to provide a mixture of rac-9b and (4-MeC6H4)2 in a 93:7 ratio (total of 45.5 mg of rac-9b 89% yield) as a colorless oil to give the final product. NMR spectrum: 1H NMR (300 MHz, CDCl3) δ1.33 (s, 3 H), 1.52 7.20 ( d, J = 8.1 Hz, 2 hours); 13C NMR spectrum (75 MHz, CDCl3) δ 17.7 (+), 18.3 (+), 21.0 (+) and 23.4 (-), 25.6 (+) or 25.8 ( +). HRMS (EI) calculated for C18H26 (M+) 242.2035 is 242.2035.

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