1667-10-3

Basic information

• Product Name: 4,4'-Bis(chloromethyl)-1,1'-biphenyl
• Synonyms: 4,4'-BIS(CHLOROMETHYL)-1,1'-BIPHENYL, 95 %;4,4'-bis(Chloromethyl)-1,1'-Bi;4,4-Dichloride-methyl-bispheny;BCMB 4,4-bis(Chloromethyl)-Biphenyl;4,4'-Bis(cnloromethyl)diphonyl;BCMP;4,4''-BIS(CHLOROMETHYL)-1,1''-BIPHENYL 95%;4,4'-bis(chloromethyl)-1,1'-biphenyl
• CAS NO: 1667-10-3
• Molecular Formula: C₁₄H₁₂Cl₂
• Molecular Weight: 251.15
• EINECS: 216-784-4
• Product Categories: Intermediates of Dyes and Pigments;Biphenyl & Diphenyl ether;Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Aryl;C13 to C37+;Halogenated Hydrocarbons;Biphenyl series
• Mol File: 1667-10-3.mol

Chemical Properties

• Melting Point: 126 °C (dec.)(lit.)
• Boiling Point: 184 °C / 0.2mmHg
• Flash Point: 196.3 °C
• Appearance: white to off-white powder
• Density: 1.195 g/cm³
• Vapor Pressure: 4.6Pa at 20℃
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Tetrahydrofuran
• Water Solubility: 200ng/L at 20℃
• CAS DataBase Reference: 4,4'-Bis(chloromethyl)-1,1'-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(chloromethyl)-1,1'-biphenyl(1667-10-3)
• EPA Substance Registry System: 4,4'-Bis(chloromethyl)-1,1'-biphenyl(1667-10-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 1667-10-3(Hazardous Substances Data)

Usage

Chemical Properties

White to light brown solid

Flammability and Explosibility

Notclassified

Upstream product

• 50-00-0 formaldehyd 
• 92-52-4 biphenyl 
• 542-88-1 bis(2-chloromethyl)ether 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 75-15-0 carbon disulfide 
• 787-70-2 4,4'-diphenic acid 
• 7647-01-0 hydrogenchloride 
• 1667-12-5 4,4'-bis(hydroxymethyl)biphenyl 

Downstream Products

• 7255-83-6 4,4’-bis(cyanomethyl)-1,1’biphenyl 
• 4433-13-0 4,4'-divinyl-biphenyl 
• 786681-04-7 2,2-bis-[4-(4'-chloromethyl-biphenyl-4-ylmethoxy)-phenyl]-indan-1,3-dione 
• 42052-87-9 4,4'-bis-trideuteriomethyl-biphenyl 
• 683805-90-5 benzyl-[4'-(benzylamino-methyl)-biphenyl-4-ylmethyl]-amine 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 29041-31-4 1,2,5,6(1,4)-tetrabenzenacyclooctaphane 
• 960041-69-4 4,4′-bis((1H-1,2,4-triazol-1-yl)methyl)biphenyl 
• 1667-12-5 4,4'-bis(hydroxymethyl)biphenyl 
• 17919-34-5 4,4'-bis(diethoxyphosphinylmethyl)biphenyl 
• 1006377-79-2 1-((4'-((pyridin-3-yloxy)methyl)biphenyl-4-yl)methyl)pyridinium-3-olate 
• 43012-19-7 [1,1'-biphenyl]-4,4'-dimethanethiol 
• 1076247-18-1 C₃₇H₃₄ClNO₆ 

Relevant articles and documents

Synthesis, antimicrobial and antifungal activity of double quaternary ammonium salts of biphenyls

The synthetic methods for new 2-, 2,2′-, and 3-substituted 4,4′-bis(chloromethyl)biphenyls were developed. Quaternization of them with various amines resulted in a series of new double quaternary ammonium salts containing the biphenyl moiety. The majority of the obtained compounds have a pronounced antifungal and antibacterial activity against the Gram-positive bacteria.

Production process of 4,4'-dichloromethylbiphenyl

The invention relates to a production process of 4,4'-dichloromethylbiphenyl, wherein the process specifically comprises the following steps: step 1, reaction: firstly, adding a solvent into a reaction kettle, adding biphenyl into the reaction kettle under stirring conditions, stirring for 15-25 min, continuing to add paraformaldehyde and a composite catalyst into the reaction kettle, controllingthe temperature of the material to be 20-40 DEG C, starting ultrasonic waves while stirring, and introducing HCl gas; and stirring and reacting for 5-8 h while ensuring that tail gas is generated, stopping introducing gas, and filtering after the reaction is finished to obtain a BCMB solution for later use; and step 2, water washing: adding purified water into a water washing kettle, adding the BCMB solution into the water washing kettle, stirring for 15-25 min, standing until layering, discharging the water phase, recovering the solvent, distilling, sending the material to a water washing crystallization kettle after distilling is finished, crystallizing at a low temperature of less than or equal to 20 DEG C, and centrifuging to obtain a BCMB crude product. the method is high in yield andshort in reaction time.

Method for preparing biphenyl benzyl dichloride through photocatalytic chlorination

The invention discloses a method for preparing biphenyl benzyl dichloride through photocatalytic chlorination. The method comprises the following steps: adding 4,4'-dimethyl biphenyl, a solvent and acatalyst into a reaction kettle, and carrying out stirring dissolution; turning on an ultraviolet lamp, and starting to introduce chlorine from the bottom; after 5 hours, monitoring the reaction process by gas chromatography, stopping the chlorine introducing when the total content of high-chlorinated products such as trichlorocompounds, tetrachlorocompounds and the like on the chromatography reaches 3%, continuously stirring for a certain time to expel residual chlorine, and then heating to evaporate out most of the solvent to obtain a crude product; and in the same reaction kettle, cooling the obtained crude product to below 40 DEG C, adding a solvent for recrystallization, continuously heating until the solvent is refluxed, completely dissolving the crude product, carrying out cooling crystallizing under stirring, filtering, and drying to obtain a white refined product.

Preparation method of 4,4'-dichloromethylbiphenyl

The invention discloses a preparation method of 4,4'-dichloromethylbiphenyl. The preparation method comprises the following steps: putting biphenyl, paraformaldehyde, acetic acid and a mesoporous silica-loaded aza-crown ether ionic liquid heterogeneous catalyst into a reaction container, introducing dry hydrogen chloride gas while stirring, and conducting stirring and reacting at 25-70 DEG C for 1-18 hours to carry out chloromethylation reaction, so as to obtain the 4,4'-dichloromethylbiphenyl. The preparation method is simple in operation and mild in reaction conditions, a catalyst can be well recovered and reused, emission of three wastes (waste gas; waste water; industrial residue) is reduced, clean cyclic production is achieved, and the method is an environment-friendly preparation method.

Catalysis preparation process for 4,4'-dichloro methyl biphenyl

The invention discloses a catalysis preparation process for 4,4'-dichloro methyl biphenyl. The catalysis preparation process comprises the steps: putting biphenyl, hydrochloric acid with the mass fraction of 27-37% and paraformaldehyde according to the weight ratio of 1:(3-4):(0.65-0.85) into a reactor, adding a solid catalyst, then adding an organic solvent, heating up to 50-80 DEG C, introducing HCl gas, carrying out a reaction for 10-20 hours, then filtering the reaction liquid to obtain the solid catalyst, allowing the liquid to stand to separate out an acid phase, washing an organic phase with water, crystallizing, and filtering to obtain a crude product, and recrystallizing the crude product to obtain the target product 4,4'-dichloro methyl biphenyl. The preparation process provided by the invention has high conversion rate; the solid catalyst can be repeatedly used, and the catalytic efficiency is not significantly reduced after the solid catalyst is repeatedly used for 40 times.

Preparation process for 4,4'-bis(chloromethyl)-1,1'-biphenyl

The invention relates to a preparation process for 4,4'-bis(chloromethyl)-1,1'-biphenyl, and belongs to the technical field of chemical synthesis. The 4,4'-bis(chloromethyl)-1,1'-biphenyl is prepared by synthesizing raw materials paraformaldehyde and biphenyl under the catalytic action of zinc chloride, acetic acid and cyclohexane. According to the process, hydrogen chloride is continuously provided for synthesis reaction by virtue of reaction of sulfuryl chloride and concentrated hydrochloric acid to ensure smooth chloromethylation reaction, so that the yield and the product quality of the 4,4'-bis(chloromethyl)-1,1'-biphenyl are improved, the amount of sewage required to be treated is small, and the treatment cost is low. According to the preparation process for the 4,4'-bis(chloromethyl)-1,1'-biphenyl, the phenomenon that an excessive amount of water is introduced into a reaction system to further reduce the catalytic effect of the zinc chloride is avoided, and moreover, production of a highly carcinogenic intermediate product is avoided; the preparation process is environment-friendly and applied to industrial expanded production, and the production cost is reduced.

A 4, 4' - dichloromethyl biphenyl preparation method

The invention discloses a production method of 4, 4'-bis (ehloromethyl) biphenyl. The production method comprises performing a chlorination reaction on 4, 4'-dimethyl biphenyl and a chlorination reagent under the action of an initiating agent and a free radical capture agent and performing after-treatment after the reaction is complete to obtain the 4, 4'-bis (ehloromethyl) biphenyl, wherein the structural formula of the 4, 4'-dimethyl biphenyl and the structural formula of the 4, 4'-bis (ehloromethyl) biphenyl are as follows. According to the production method of the 4, 4'-bis (ehloromethyl) biphenyl, raw materials which are low in price and easy to obtain are utilized, the target compound is obtained through the one-step reaction, and accordingly the cost is low, the operation is simple and convenient, the yield is high, the environment-friendly effect is achieved, and the production method is suitable for industrial production.

Method for catalytically synthesizing 4,4'-bischloromethylbiphenyl by using silicon dioxide-loaded phosphotungstic acid

The invention relates to a method for catalytically synthesizing 4,4'-bischloromethylbiphenyl by using silicon dioxide-loaded phosphotungstic acid, which comprises the steps: charging biphenyl, 30-37% hydrochloric acid and paraformaldehyde into a reactor according to a molar ratio of 1:(2-8):(3-4), adding the silicon dioxide-loaded phosphotungstic acid catalyst, then adding an organic solvent, heating to 50-80 DEG C, introducing HCl gas, reacting for 10-20h, and performing posttreatment and crude product recrystallization on the reaction solution to obtain a target product 4,4'-bischloromethylbiphenyl. The method has the advantages that the catalyst can be repeatedly used and regenerated and an acid phase is used indiscriminately, a conversion rate of the 4,4'-bischloromethylbiphenyl is obviously improved, a yield after refinement is 89%, content is 99% or above, emission of three wastes is reduced, clean and circulation production is realized and the method is an environment-friendly preparation method.

Efficient dichloromethylation of some aromatic hydrocarbons catalyzed by a new ionic liquid [C12minPEG800]br under homogeneous catalysis in aqueous media

A series of new imidazolium-type ionic liquids based on polyethylene glycol have been prepared. The new recyclable temperature-dependant phase-separation system comprised of [C12minPEG800]Br and methylcyclohexane was also developed and successfully applied to the dichloromethylation of some aromatic hydrocarbons to prepare dichloromethyl-substituted hydrocarbons in excellent yields. The ionic liquid could be excellent recycled without any apparent loss of catalytic activity and little loss of weight even after 8 times recycling.

An inexpensive and convenient procedure for chloromethylation of aromatic hydrocarbons by phase transfer catalysis in aqueous media

Reaction of aromatic hydrocarbons catalyzed by a novel catalytic system consisting of zinc chloride, acetic acid, sulfuric acid and PEG-800 in aqueous media under PTC conditions results in chloromethylation in good to excellent yield.