1667-11-4

Basic information

• Product Name: 4-Chloromethylbiphenyl
• Synonyms: 4-(chloromethyl)-bipheny;4CMB;4-cmb;p-Phenylbenzyl Chloride;p-phenylbenzylchloride;4-Chloromethylbiphen;4-Phenylbenzyl chloride 98%;4-PHENYLBENZYL CHLORIDE
• CAS NO: 1667-11-4
• Molecular Formula: C₁₃H₁₁Cl
• Molecular Weight: 202.68
• EINECS: 216-786-5
• Product Categories: Biphenyl & Diphenyl ether;Biphenyl series
• Mol File: 1667-11-4.mol

Chemical Properties

• Melting Point: 70-73 °C(lit.)
• Boiling Point: 321.03°C (rough estimate)
• Flash Point: 143.2 °C
• Appearance: White ro Off-white crystalline powder
• Density: 1.1339 (estimate)
• Vapor Pressure: 0.000527mmHg at 25°C
• Refractive Index: 1.5945 (estimate)
• BRN: 1863327
• CAS DataBase Reference: 4-Chloromethylbiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloromethylbiphenyl(1667-11-4)
• EPA Substance Registry System: 4-Chloromethylbiphenyl(1667-11-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DV2087000
• F: 21
• HazardClass: IRRITANT
• Hazardous Substances Data: 1667-11-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloromethylbiphenyl is used as a key intermediate in the synthesis of non-steroidal anti-inflammatory drugs (NSAIDs) for its ability to contribute to the development of effective medications. It plays a crucial role in the production of 4-biphenylacetic acid and fenbufen, which are NSAIDs known for their anti-inflammatory and analgesic properties.
Used in Drug Development:
4-Chloromethylbiphenyl is also utilized in the synthesis of felbinacethyl, another anti-inflammatory and analgesic drug. The presence of the chloromethyl group in 4-Chloromethylbiphenyl allows for the creation of various drug derivatives that can target specific conditions and provide relief.
Used in Polymer Liquid Crystal Industry:
4-Chloromethylbiphenyl is used as a building block in the development of polymer liquid crystals, which are materials with unique properties that combine aspects of both liquid crystals and polymers. Its incorporation into these materials can enhance their performance and expand their range of applications.
Used in Dye Industry:
In the dyestuff sector, 4-Chloromethylbiphenyl serves as a valuable precursor for the synthesis of various dyes. Its chemical structure allows for the creation of dyes with specific color properties and stability, making it an essential component in the production of high-quality dyes for different applications.

InChI:InChI=1/C13H11Cl/c14-10-11-6-8-13(9-7-11)12-4-2-1-3-5-12/h1-9H,10H2

Upstream product

• 50-00-0 formaldehyd 
• 92-52-4 biphenyl 
• 3597-91-9 biphenyl-4-yl methanol 
• 644-08-6 4-Methylbiphenyl 
• 7647-01-0 hydrogenchloride 
• 238428-24-5 [1,1'-biphenyl-4-yl]methanamine monohydrochloride 
• 3315-91-1 4-biphenylylmagnesium bromide 
• 191097-22-0 2-(2-tert-butyldimethylsiloxyethyl)-4H-benzo[1,4]oxazin-3-one 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 3218-36-8 4-Phenylbenzaldehyde 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 100-58-3 phenylmagnesium bromide 
• 591-51-5 phenyllithium 
• 589-17-3 p-bromobenzyl chloride 

Downstream Products

• 262371-18-6 1-([1,1’-biphenyl]-4-yl)-N-benzyl-N-methylmethanamine 
• 861342-35-0 methyl-(4-methyl-benzyl)-(4-phenyl-benzyl)-amine 
• 857785-79-6 (4-cyclohexyl-benzyl)-methyl-(4-phenyl-benzyl)-amine 
• 31603-77-7 4-biphenylacetonitrile 
• 644-08-6 4-Methylbiphenyl 
• 3218-36-8 4-Phenylbenzaldehyde 
• 110931-72-1 methyl-(4-phenyl-benzyl)-amine 
• 858428-55-4 methyl-bis-(4-phenyl-benzyl)-amine 
• 94578-87-7 2-biphenyl-4-ylmethylsulfanyl-benzothiazole 
• 61439-48-3 p-<(4-Biphenylmethyl)amino>benzoesaeureethylester 
• 94751-35-6 S,S'-bis(p-phenylbenzyl)dihydroasparagusate 
• 110951-66-1 methyl-[1]naphthylmethyl-(4-phenyl-benzyl)-amine 
• 129760-22-1 lycoctonine 18-O-p-phenyl-benzyl ether 
• 132213-91-3 (-)-1-O-(biphenylylmethyl)-Δ⁸-tetrahydrocannabinol 

Related news

An assessment of the clastogenic potential of 4-Chloromethylbiphenyl (cas 1667-11-4) in human lymphocytes in vitro09/26/2019

The clastogenic potential of 4CMB was assessed in vitro in human lymphocytes from 4 donors (2 male and 2 female) both with and without auxiliary metabolic activation. Although there were some variation in the response of the cells from different donors to 4CMB using 2 criteria for interpretation...detailed

Benzyl chloride and 4-Chloromethylbiphenyl (cas 1667-11-4) induced DNA damage and its repair in excision-deficient (XP group A) or -proficient human cells09/24/2019

Benzyl chloride (BC) and 4-chloromethylbiphenyl (4CMB) induce a class of alkaline-stable DNA damage in human cells which, like UV-induced pyrimidine dimers, undergoes repair at a slow rate by an excision-repair pathway which can be inhibited by cytosine arabinoside (araC). In the present study, ...detailed

DNA damage and its repair in cultured human alveolar tumor cells treated with benzyl chloride, 4-Chloromethylbiphenyl (cas 1667-11-4) or 4-hydroxymethylbiphenyl09/10/2019

Both benzyl chloride and 4-chloromethylbiphenyl induce repairable types of DNA damage in cultured human cells. No DNA damage can be detected after treatment with 4-hydroxymethylbiphenyl.detailed

Mutagenicity of 4-Chloromethylbiphenyl (cas 1667-11-4) in the salmonella/microsome assay09/08/2019

The mutagenic activity of 4-chloromethylbiphenyl was determined in Salmonella typhimurium strains TA1535, TA1537, TA98, and TA100 using the plate-incorporation assay with and without rat-liver S9. The compound was positive in strains TA1537, TA98, and TA100 both with and without S9 activation. A...detailed

The assay of 4-Chloromethylbiphenyl (cas 1667-11-4) in the dominant lethal assay in mice09/07/2019

4-Chloromethylbiphenyl (4CMB) was tested in mice in a dominant lethal assay over 4 weeks. Ethyl methanesulphonate (EMS) was used as the positive control. 4CMB did not elicit a dominant lethal response though EMS produced the expected result.detailed

Relevant articles and documents

Multiple-photon ? chemistry in the laser-jet: Photochemistry of the 4-biphenylmethyl radical

In laser-jet (LJ) photolysis (high intensity) of the ether 4-(4-benzoylphenoxymethyl)biphenyl 1 a two-photon process is observed in CCl4 to yield 4-(chloromethyl)biphenyl 5 as product (3%), while the one-photon product is 4-biphenylaldehyde 7 (100% in conventional photolysis versus 97% in laser-jet photolysis). In ethanol, the results suggest a three-proton reaction in which 4-(ethoxymethyl)biphenyl 6 is produced in appreciable amounts (18%) in addition to the one-photon product 1,2-bis(4-biphenyl)ethane 4, the latter as the major product (82%). It is proposed that under high-intensity LJ photolysis conditions the electronically-excited 4-biphenylmethyl radical 2* is photoionized to the 4-biphenylmethyl cation 2+ and that the latter is trapped by ethanol to give the 4-biphenylmethyl ether 6.

Palladium-anchored multidentate SBA-15/di-urea nanoreactor: A highly active catalyst for Suzuki coupling reaction

Modification of mesoporous silica was carried out by reaction of SBA-15 with di-urea-based ligand. Next, with the help of this ligand, palladium ions were anchored within the multidentate SBA-15/di-urea pore channels with high dispersion. The SBA-15/di-urea/Pd catalyst was characterized using various techniques. Theoretical calculations indicated that each palladium ion was strongly interacted with one nitrogen and two oxygen atoms from the multidentate di-urea ligand located in SBA-15 channels and these interactions remained during the catalytic cycle. These results are in good agreement with those of hot filtration test: the palladium ions have very high stability against leaching from the SBA-15/di-urea support. The catalytic performance of SBA-15/di-urea/Pd nanostructure was examined for the Suzuki coupling reaction of phenylboronic acid and electronically diverse aryl halides under mild conditions with a minimal amount of Pd (0.26?mol%). Compared to previous reports, this protocol afforded some advantages such as short reaction times, high yields of products, catalyst stability without leaching, easy catalyst recovery and preservation of catalytic activity for at least six successive runs.

Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol

The mechanism of solvolyses of activated ortho-, meta- and para-substituted benzyl chlorides in aqueous ethanol has been studied by using the Hammett-Brown and Yukawa-Tsuno treatments as well as by correlating logarithms of solvolysis rate constants with relative stabilities of corresponding benzyl carbocations in water calculated at the IEFPCM-M06–2X/6-311+G(3df,3pd) level of theory. Benzyl chlorides containing strong conjugative electron-donors in the para-position solvolyze by the SN1 mechanism, whereas other activated benzyl chlorides solvolyze by the SN2 mechanism via loose transition states.

Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones

An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is

Synthesis and evaluation of tetrahydroisoquinoline derivatives against Trypanosoma brucei rhodesiense

Human African Trypanosomiasis (HAT) is a neglected tropical disease caused by the parasitic protozoan Trypanosoma brucei (T. b.), and affects communities in sub-Saharan Africa. Previously, analogues of a tetrahydroisoquinoline scaffold were reported as having in vitro activity (IC50 = 0.25–70.5 μM) against T. b. rhodesiense. In this study the synthesis and antitrypanosomal activity of 80 compounds based around a core tetrahydroisoquinoline scaffold are reported. A detailed structure activity relationship was revealed, and five derivatives (two of which have been previously reported) with inhibition of T. b. rhodesiense growth in the sub-micromolar range were identified. Four of these (3c, 12b, 17b and 26a) were also found to have good selectivity over mammalian cells (SI > 50). Calculated logD values and preliminary ADME studies predict that these compounds are likely to have good absorption and metabolic stability, with the ability to passively permeate the blood brain barrier. This makes them excellent leads for a blood-brain barrier permeable antitrypanosomal scaffold.

Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes

Herein, we report a nickel-catalyzed asymmetric two-component reductive dicarbofunctionalization of aryl iodide-tethered unactivated alkenes using benzyl chlorides as the challenging coupling partner. This arylbenzylation reaction enables the efficient synthesis of diverse benzene-fused cyclic compounds bearing a quaternary stereocenter with a high tolerance of sensitive functionalities in highly enantioselective manner. The preliminary mechanistic investigations suggest a radical chain reaction mechanism.

Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide

By combining "N-chlorosuccinimide (NCS)"as the safe chlorine source with "Acr+-Mes"as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor "N-centered succinimidyl radical,"which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr?-Mes.

Biphenyl acetic acid and preparation method thereof

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Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C-H Acetoxylation Catalyzed by Pd(OAc)2/4,5-Diazafluoren-9-one

Allylic C-H acetoxylations are among the most widely studied palladium(II)-catalyzed C-H oxidation reactions. While the principal reaction steps are well established, key features of the catalytic mechanisms are poorly characterized, including the identity of the turnover-limiting step and the catalyst resting state. Here, we report a mechanistic study of aerobic allylic acetoxylation of allylbenzene with a catalyst system composed of Pd(OAc)2 and 4,5-diazafluoren-9-one (DAF). The DAF ligand is unique in its ability to support aerobic catalytic turnover, even in the absence of benzoquinone or other co-catalysts. Herein, we describe operando spectroscopic analysis of the catalytic reaction using X-ray absorption and NMR spectroscopic methods that allow direct observation of the formation and decay of a palladium(I) species during the reaction. Kinetic studies reveal the presence of two distinct kinetic phases: (1) a burst phase, involving rapid formation of the allylic acetoxylation product and formation of the dimeric PdI complex [PdI(DAF)(OAc)]2, followed by (2) a post-burst phase that coincides with evolution of the catalyst resting state from the PdI dimer into a π-allyl-PdII species. The data provide unprecedented insights into the role of ancillary ligands in supporting catalytic turnover with O2 as the stoichiometric oxidant and establish an important foundation for the development of improved catalysts for allylic oxidation reactions.

α-Diimine-Niobium Complex-Catalyzed Deoxychlorination of Benzyl Ethers with Silicon Tetrachloride

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