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
• Article Data: 38

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

Description

4-Chloromethylbiphenyl, also known as 4-(Chloromethyl)biphenyl, is an important biphenyl derivative characterized by the presence of a chloromethyl group attached to the biphenyl structure. 4-Chloromethylbiphenyl exhibits unique chemical properties that make it valuable in various industries.

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

• 92-52-4 biphenyl 
• 109-87-5 Dimethoxymethane 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 98-80-6 phenylboronic acid 
• 589-17-3 p-bromobenzyl chloride 
• 3218-36-8 4-Phenylbenzaldehyde 
• 3597-91-9 biphenyl-4-yl methanol 
• 191097-22-0 2-(2-tert-butyldimethylsiloxyethyl)-4H-benzo[1,4]oxazin-3-one 
• 3315-91-1 4-biphenylylmagnesium bromide 
• 238428-24-5 [1,1'-biphenyl-4-yl]methanamine monohydrochloride 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 644-08-6 4-Methylbiphenyl 
• 68941-68-4 bis(4-biphenylmethyl) ether 

Downstream Products

• 3597-91-9 biphenyl-4-yl methanol 
• 31603-77-7 4-biphenylacetonitrile 
• 30203-83-9 4-(4-bromobenzyl)-1,1'-biphenyl 
• 1638139-71-5 4-(3-methyl-2-(1-phenylvinyl)benzyl)-1,1'-biphenyl 
• 1192485-86-1 2-[1-(1,1'-biphenyl-4-ylmethyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide 
• 172648-17-8 [3-(4-phenylbenzyl)-3H-imidazo[4,5-b]pyridin-2-yl]methanol 
• 167147-45-7 5'-O-(4-phenylbenzyl)thymidine 
• 172732-92-2 1-([1,1'-biphenyl]-4-ylmethyl)-4-methoxy-2-methyl-1H-indole 
• 35888-99-4 3-(4-biphenylyl)propionic acid 
• 857785-79-6 (4-cyclohexyl-benzyl)-methyl-(4-phenyl-benzyl)-amine 
• 259816-87-0 (1-biphenyl-4-ylmethyl-4-pyridin-4-yl-1H-pyrrol-3-yl)-imidazol-1-yl-methanone 
• 259816-86-9 1-(4-biphenylmethyl)-4-(4-pyridinyl)pyrrole-3-carboxylic acid 

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.

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.

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.

Biphenyl acetic acid and preparation method thereof

The invention discloses biphenyl acetic acid and a preparation method thereof. The preparation method comprises the following steps: dissolving bromobenzene into dimethylformamide, and performing reaction under the action of palladium powder to obtain biphenyl; dissolving biphenyl in cyclohexane, and performing chloromethylation reaction on biphenyl in a hydrochloric acid solution and a saturatedformaldehyde aqueous solution to obtain an intermediate 1; dissolving sodium cyanide in deionized water, and performing cyanidation reaction on the intermediate 1 and a sodium cyanide aqueous solutionunder the action of a catalyst n-butylammonium bromide to obtain an intermediate 2; and further hydrolyzing the intermediate 2 under the condition of an alkaline aqueous solution, and performing acidifying under the action of hydrochloric acid to obtain biphenyl acetic acid. The yield of the biphenyl acetic acid prepared by the aid of the method is higher than that of the biphenyl acetic acid prepared by the aid of traditional processes, reactants are low in price, the preparation cost of the biphenyl acetic acid can be greatly reduced, and the method is favorable for market popularization.