101-76-8

Basic information

• Product Name: 4,4'-DDM
• Synonyms: 1,1’-methylenebis(4-chloro-benzen;1,1’-methylenebis[4-chloro-benzen;1,1’-methylenebis[4-chloro-Benzene;1-Chloro-4-(4-chlorobenzyl)benzene;4,4’-dichlorodiphenylmethane;4,4'-Dichlorodiphenylmethane;Benzene, 1,1'-methylenebis*4-chloro-;bis(4-chlorophenyl)-methan
• CAS NO: 101-76-8
• Molecular Formula: C₁₃H₁₀Cl₂
• Molecular Weight: 237.12
• EINECS: 202-973-9
• Mol File: 101-76-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 55.5°C
• Boiling Point: 308.48°C (rough estimate)
• Flash Point: 139.8°C
• Appearance: /
• Density: 1.3650
• Refractive Index: 1.6030 (estimate)
• BRN: 1873121
• CAS DataBase Reference: 4,4'-DDM(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DDM(101-76-8)
• EPA Substance Registry System: 4,4'-DDM(101-76-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: PA3925000
• Hazardous Substances Data: 101-76-8(Hazardous Substances Data)

Usage

Definition

ChEBI: A chlorophenylmethane that is methane in which two of the hydrogens have been replaced by p-chlorophenyl groups.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofCl-.

Upstream product

• 72-55-9 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene 
• 141-52-6 sodium ethanolate 
• 83-05-6 bis(4'-chlorophenyl)acetic acid 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 108-90-7 chlorobenzene 
• 542-88-1 bis(2-chloromethyl)ether 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 67-56-1 methanol 
• 5463-11-6 4,4'-dichlorobenzophenone hydrazone 
• 7727-15-3 aluminium bromide 
• 100-39-0 benzyl bromide 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 782-08-1 chlorobis(4-chlorophenyl)methane 

Downstream Products

• 6306-46-3 1-[bromo(4-chlorophenyl)methyl]-4-chlorobenzene 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 782-08-1 chlorobis(4-chlorophenyl)methane 
• 7498-65-9 4,4'-dichloro-3,3'-dinitrobenzophenone 
• 2973-18-4 4,4'-Dichloro-3,3'-dinitrodiphenylmethane 
• 7457-25-2 bis-(4-chlorophenyl)-dichloromethane 
• 13144-33-7 1,1,2,2-tetrakis(4-chlorophenyl)ethane 
• 457-68-1 4,4'-difluorodiphenylmethane 
• 1289648-65-2 2-(bis(4-chlorophenyl)methyl)-1,3-diphenylpropane-1,3-dione 
• 15876-05-8 4,4'-dichlorobenzhydrylium ion 
• 19685-62-2 N,N-dimethyl[bis(4-chlorophenyl)methyl]amine 
• 79506-28-8 bis(4-chloro-3-sulfophenyl)methane, disodium salt 
• 2191-79-9 bis(4-chloro-3-sulfamoylphenyl)methane 
• 79506-26-6 bis(4-chloro-3-chlorosulfonylphenyl)methane 

Relevant articles and documents

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Deoxygenation of tertiary and secondary benzylic alcohols into alkanes with triethylsilane catalyzed by solid acid tin(IV) ion-exchanged montmorillonite

We discovered an efficient protocol for the conversion of tertiary and secondary benzylic alcohols into the corresponding alkanes in good to quantitative yields by employing tin(IV) ion-exchanged montmorillonite (Sn-Mont) as a solid acid catalyst and Et3SiH as the hydride source. The reaction is likely to proceed via the SN1-type reaction mechanism, that is, the formation of carbenium ions, followed by the addition of a hydride from the silane. The work-up of the reaction only requires simple filtration of the solid acid without any neutralization of the acid catalyst.

Preparation of Dihalobenzophenones by Oxidation under Phase-Transfer-Catalysis Conditions

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Selective preparation of 4,4′-dichlorodiphenylmethane over zeolite K-L catalyst using sulfuryl chloride

The liquid phase chlorination of diphenylmethane (DPM) to 4,4′-dichlorodiphenylmethane (4,4′-DCDPM) is investigated at 333 K, under atmospheric pressure over a number of zeolite catalysts using sulfuryl chloride (SO2Cl2) as the chlorinating agent. The results obtained are compared with those over the conventional Lewis acid catalyst, AlCl3 as well as without any catalyst. Zeolite K-L is found to be highly active and selective catalyst for the conversion of DPM to 4,4′-DCDPM. The conversion of DPM, rate of DPM conversion and the selectivity (4,4′-DCDPM/2,4′-DCDPM isomer ratio) over zeolite K-L after 1 h of reaction time are found to be 96.8 wt.%, 19.1 mmol g-1 h-1 and 7.4, respectively. The influence of solvent, catalyst concentration, reaction temperature, DPM/SO2Cl2 molar ratio, recycle of zeolite K-L, etc. are also examined. 1,2-Dichloroethane is the best solvent and gives the highest selectivity for 4,4′-DCDPM (4,4′-DCDPM/2,4′-DCDPM isomer ratio = 9.7) with zeolite K-L at 353 K after 1 h of reaction time. The formation of 4,4′-DCDPM is favoured by increase in catalyst concentration, reaction temperature and higher concentration of SO2Cl2 (lower DPM/SO2Cl2 molar ratio). In all these cases, the yield of 4,4′-DCDPM increases with a decrease in the yield of 4-CDPM which suggests that the formation of 4,4′-DCDPM takes place by the consecutive reaction of 4-CDPM. Higher SiO2/Al2O3 ratio (obtained by HCl treatment) of zeolite K-L decreases the conversion of DPM. A noticeable decrease in the activity and selectivity of zeolite K-L is observed on recycling, probably due to reduced crystallinity as well as extraction of small amounts of Al+3 and K+ ions by the HCl, generated in the reaction. Mechanistically, SO2Cl2 is first decomposed into SO2 and Cl2 the latter being polarized by the zeolite catalyst to an electrophile (Cl+) which then attacks the DPM and subsequently produce the monochlorodiphenylmethane (MCDPM). The MCDPM further is attacked by the electrophile (Cl+) and result in the formation of DCDPM.

Preparation method 4,4 ' -difluorobenzophenone and intermediate thereof

The invention discloses 4-4' -difluorobenzophenone and a preparation method of an intermediate thereof. The preparation method of 4, 4 '- difluorobenzophenone comprises the following steps: S1: 4 - chlorobenzyl chloride and chlorobenzene react under first catalyst to obtain 4, 4' -dichlorophenylmethane. The first catalyst is Lewis acid and/or a molecular sieve with Lewis acid center. S2: The 4, 4 '-dichlorophenylmethane and oxidant are subjected to an oxidation reaction under the action second catalyst to obtain 4, 4' -dichlorobenzophenone. S3: The 4, 4' -dichlorobenzophenone and the alkali metal fluoride are subjected to a halogenation reaction to obtain the invention. The 4' - difluorobenzophenone and the intermediate thereof disclosed by the invention are high in selectivity, high in yield, low in raw material cost, mild in process condition, high in safety and wide in industrial prospect.

Nitrenium Salts in Lewis Acid Catalysis

Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry. By contrast, electrophilic nitrogen-containing compounds are much rarer. Nitrenium cations are a new family of nitrogen-based Lewis acids, the reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations. These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover, these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture, allowing for benchtop transformations without the need to pretreat solvents.

Novel process for producing phenyl fluoride, diphenyl ketone fluoride, and derivatives thereof

The invention relates to a novel process for producing phenyl fluoride, diphenyl ketone fluoride, and derivatives thereof, especially the phenyl fluoride and derivatives thereof. The invention especially relates to a novel environment-friendly process for synthesizing phenyl fluoride and diphenyl ketone fluoride, which are the raw materials for preparing polyaryl-ether-ketone PAEK. The invention discloses the method that is more effective and environment-friendly for preparing the compounds through a Friedel-Crafts reaction, and further a more environment-friendly process, and provdies beneficial catalysts. Another object of the present invention is to employ the Friedel-Crafts reaction and adopts the beneficial catalysts, wherein the catalyst can be easily combined with the fluoridation reaction which can be carried out before, or after the Friedel-Crafts reaction. Herein, another object of the invention is to use the catalyst in the Friedel-Crafts reaction, wherein the catalyst can work in both the Friedel-Crafts reaction and the fluoridation reaction.