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3-(3-(Trifluoromethyl)phenyl)propanoyl chloride is a chemical compound with the molecular formula C10H8ClF3O2. It is a colorless to pale yellow liquid with a molecular weight of 254.62 g/mol. 3-(3-(trifluoroMethyl)phenyl)propanoyl chloride is an aromatic acyl chloride derivative, featuring a trifluoromethyl group attached to a phenyl ring, which is connected to a propanoyl chloride moiety. It is synthesized by reacting 3-(trifluoromethyl)phenylacetic acid with thionyl chloride or oxalyl chloride. 3-(3-(trifluoroMethyl)phenyl)propanoyl chloride is used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals due to its reactivity and the presence of the electron-withdrawing trifluoromethyl group. It is important to handle 3-(3-(trifluoroMethyl)phenyl)propanoyl chloride with care, as it is sensitive to hydrolysis and can react with nucleophiles, such as amines and alcohols, to form amides and esters, respectively.

455-03-8

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455-03-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 455-03-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 5 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 455-03:
(5*4)+(4*5)+(3*5)+(2*0)+(1*3)=58
58 % 10 = 8
So 455-03-8 is a valid CAS Registry Number.

455-03-8Relevant academic research and scientific papers

Preparation method of cinacalcet hydrochloride

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Paragraph 0036; 0038; 0040, (2020/10/05)

The invention provides a preparation method of cinacalcet hydrochloride, which comprises the following steps: (1) reacting a compound as shown in a formula I with thionyl chloride under the conditionsthat isopropyl acetate and N, N-dimethylformamide are used as solvents and the temperature is 40-45 DEG C to obtain a product; (2) directly reacting the product obtained in the step (1) with a raw material A to obtain an intermediate I; and (3) carrying out reduction reaction and refining on the intermediate I obtained in the step (2) to obtain cinacalcet hydrochloride. According to the preparation method provided by the invention, by using isopropyl acetate and N, N-dimethylformamide (DMF) as solvents in the first-step reaction, compared with the prior art requiring the reaction conditions of higher reaction temperature and a large amount of thionyl chloride, the temperature is greatly reduced, the use amount of thionyl chloride is reduced, higher yield is still ensured, and the method has higher industrialization value.

Method for synthesizing cinacalcet intermediate

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Paragraph 0007; 0013-0019, (2020/04/02)

The invention particularly discloses a method for preparing a cinacalcet hydrochloride intermediate (R)-N-(1-(naphthalen-1-yl)ethyl-3-(trifluoromethyl)phenyl)propanamide. The method comprises the following steps: 3-(3-trifluoromethylphenyl)propionic acid

Method for synthesizing cinacalcet hydrochloride intermediate in microchannel reactor

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Paragraph 0065-0081; 0087-0089, (2019/11/12)

The invention provides a method for synthesizing cinacalcet hydrochloride intermediate in a microchannel reactor. The method comprises the steps that 3-(3-trifluoromethylphenyl)-2-acrylic acid and a supported noble metal catalyst are added into an organic solvent A to react with hydrogen to generate 3-(3-trifluoromethylphenyl)propionic acid; after the reaction, filtration is conducted, and a catalyst B and thionyl chloride are added into filtrate to react to generate 3-(3-trifluoromethylphenyl)propionyl chloride, and the two intermediates are all finished in the microchannel reactor. By usingefficient mass transfer and heat transfer of the microchannel reactor, time of hydrogenation is effectively shortened, generation of esterification by-products in the hydrogenation process is prevented, the purity and yield of products are improved, palladium carbon is recovered and applied ,mechanically for many times, cumbersome operation in the kettle reaction process is overcome, and at the same time, materials generated in the reaction can be directly used for the next reaction; and the usage amount of the thionyl chloride in the preparation process of acyl chloride is reduced, waste discharge is reduced, and a green process for synthesizing cinacalcet hydrochloride intermediate is provided.

Enantioselective synthesis of (R)-Cinacalcet via cobalt-catalysed asymmetric Negishi cross-coupling

Sun, Xiao,Wang, Xueyang,Liu, Feipeng,Gao, Zidong,Bian, Qinghua,Wang, Min,Zhong, Jiangchun

, p. 682 - 687 (2019/08/07)

A novel enantioselective synthesis of (R)-cinacalcet with 99% enantiomeric excesses (ee) has been achieved. The main strategies of the approach include a gram-scale cobalt-catalysed asymmetric cross-coupling of racemic ester with arylzinc reagent, Hoffman-type rearrangement of acidamide, the amidation of chiral amine, and improving the ee of chiral amide from 87% to 99% via recrystallization.

Rh(III)-Catalyzed meta-C-H Olefination Directed by a Nitrile Template

Xu, Hua-Jin,Lu, Yi,Farmer, Marcus E.,Wang, Huai-Wei,Zhao, Dan,Kang, Yan-Shang,Sun, Wei-Yin,Yu, Jin-Quan

supporting information, p. 2200 - 2203 (2017/02/23)

A range of Rh(III)-catalyzed ortho-C-H functionalizations have been developed; however, extension of this reactivity to remote C-H functionalizations through large-ring rhodacyclic intermediates has yet to be demonstrated. Herein we report the first examp

A hydrochloride [...] synthesis and refining method

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Paragraph 0039; 0045; 0046, (2017/02/09)

The invention explores a method for synthesizing and refining cinacalcet hydrochlorid, especially avoids toxic and expensive reaction reagents reported in literatures; the invention has the advantages of convenient sources of raw materials and reagents, low cost, little pollution to environment and simple operation, the invention is suitable for industrial production.

Cross-coupling of remote meta -c-h bonds directed by a u-shaped template

Wan, Li,Dastbaravardeh, Navid,Li, Gang,Yu, Jin-Quan

supporting information, p. 18056 - 18059 (2014/01/06)

meta-C-H arylation and methylation of 3-phenylpropanoic acid and phenolic derivatives were developed using an easily removable nitrile template. The combination of a weakly coordinating U-shaped template and mono-protected amino acid ligand was crucial fo

GSK-3BETAINHIBITOR

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Page/Page column 59, (2010/04/23)

For the purpose of providing a GSK-3β inhibitor containing an oxadiazole compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof.

Efficient synthesis of cinacalcet hydrochloride

Bijukumar, Gopinathenpillai,Maloyesh, Biswas,Bhaskar, Bhirud Shekhar,Rajendra, Agarwal

, p. 1512 - 1517 (2008/09/20)

A new route to synthesize cinacalcet hydrochloride ((R)-α-methyl-N- [3-[3-(trifluoromethyl) phenyl] propyl]-1-naphthalene methane amine hydrochloride) has been described. The key steps include the Knoevenagel-Doebner condensation and the amide reduction under milder conditions. Copyright Taylor & Francis Group, LLC.

DATA PROCESSING DEVICE, PARTICULARLY A SET-TOP BOX FOR CONNECTION TO A RECEIVER, INPUT DEVICE FOR THE CONTROL OF A DATA PROCESSING DEVICE, AND METHOD FOR OPERATING A DATA PROCESSING DEVICE

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Page/Page column 27, (2008/06/13)

The invention relates to a data processing device, particularly a set-top box, and a method for operating the data processing device (16). The data processing device (16) is provided for the connection to a receiver (15) and a communication network. The data processing device (16) is configured to receive and process data sent from the communication network, comprising content data (2) and at least one identification date (3), and to transmit the processed data to the receiver (15) for the output thereof. The data processing device (16) is further configured to receive and process a code sent by an input device of the data processing device and/or of the receiver (15), the code being associated with a certain identification date (3) of the identification data. In response to the receipt of the code, a communication connection is established between the data processing device (16), or a communication terminal (19), and a unit of the communication network, which is associated with the certain identification date (3).

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