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2-Phenyl-propionyl chloride, with the molecular formula C9H9ClO, is an organic compound that falls under the category of cinnamic acid derivatives. It is derived from phenylalanine and features a cinnamic acid moiety. 2-Phenyl-propionyl chloride is typically a clear to pale yellow liquid, with a melting point of -75 degrees Celsius and a boiling point of 247 degrees Celsius. Due to its potential to cause burns and other serious health hazards, it must be handled with caution, particularly to avoid skin and eye contact, and used in a controlled environment with strict adherence to safety protocols.

22414-26-2

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22414-26-2 Usage

Uses

Used in Organic Synthesis:
2-Phenyl-propionyl chloride is used as a reagent for the formation of amides and esters in various organic synthesis processes. Its versatility in these reactions makes it a valuable component in the creation of a wide range of chemical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Phenyl-propionyl chloride is used as a key intermediate in the synthesis of various drugs. Its ability to form amides and esters is crucial for the development of new medicinal compounds with potential therapeutic applications.
Used in Chemical Research:
2-Phenyl-propionyl chloride is also utilized in chemical research as a model compound for studying the properties and reactions of cinnamic acid derivatives. This helps in understanding the broader chemical behavior of similar compounds and contributes to the advancement of organic chemistry.

Check Digit Verification of cas no

The CAS Registry Mumber 22414-26-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,4,1 and 4 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 22414-26:
(7*2)+(6*2)+(5*4)+(4*1)+(3*4)+(2*2)+(1*6)=72
72 % 10 = 2
So 22414-26-2 is a valid CAS Registry Number.

22414-26-2 Well-known Company Product Price

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  • Aldrich

  • (689548)  2-Phenylpropionylchloride  ≥95%

  • 22414-26-2

  • 689548-1G

  • 769.86CNY

  • Detail

22414-26-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Phenylpropanoyl chloride

1.2 Other means of identification

Product number -
Other names 2-phenylpropionic acid chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22414-26-2 SDS

22414-26-2Relevant academic research and scientific papers

Readily Removable Directing Group Assisted Chemo- and Regioselective C(sp3)-H Activation by Palladium Catalysis

Zhang, Yun-Fei,Zhao, Hong-Wei,Wang, Hui,Wei, Jiang-Bo,Shi, Zhang-Jie

, p. 13686 - 13690 (2015)

Currently used directing groups for selective aliphatic β-functionalization of carbonyl compounds show excellent reactivity and selectivity with an amide as a linker. Described herein is 2-piconimide, used for the first time with commercially available 2-picolinamide/2-picolic acid as precursors, to direct C-H arylation/alkenylation by palladium catalysis. The directing group is essential for promoting the sequnetial primary and secondary C(sp3)-H arylation with different aryl iodides in one substrate. The directing group was easily removed under simple reaction conditions at room temperature.

Structures and ambident reactivities of azolium enolates

Maji, Biplab,Mayr, Herbert

, p. 11163 - 11167 (2013)

Oxygen versus carbon: Azolium enolates were generated by the reactions of N-heterocyclic carbenes (NHCs) with methyl phenyl ketene and characterized by X-ray crystallography. Kinetic studies show that the enolate oxygen is 20 times more nucleophilic than

Synthesis and in vitro anti-platelet aggregation activities of 2-methoxy-5-arylamido-N-(pyridin-3-yl-methyl)benzamides

Wang, Yan,Wang, Xiao,Chen, Xin,Liu, Xiujie

, (2019)

In order to discover novel compounds with anti-platelet aggregation activities, a series of novel 2-methoxy-5-arylamido-N-(pyridin-3-ylmethyl)benzamides (1a–n) were synthesized and their anti-platelet aggregation activities were evaluated by the turbidimetric method in response to the following agonists: adenosine diphosphate (ADP) (5 mM/L), arachidonic acid (AA) (20 μM/L), and collagen (1 mg/mL). Those synthesized compounds that have better in vitro activities were subjected to cell toxicity tests via cell counting kit-8 (CCK-8) assay. The biological evaluation revealed that compound 1a (IC50: 0.21 μM/L) exhibited the highest anti-platelet aggregation activities when ADP was selected as an inducer, and compound 1b (IC50: 0.23 μM/L) showed the best activities when AA was selected as inducer, and compound 1m (inhibition rate: 55.06%) had significant anti-platelet aggregation activities when collagen was selected as inducer among all target compounds. Moreover, the effect of cell toxicity exhibited that none of the compounds had obvious cell toxicity against L929 cells. Therefore, 2-methoxy-5-arylamido-N-(pyridin-3-ylmethyl)benzamides have the potential to become a novel kind of anti-platelet drugs and deserve further study.

ACYLAMINO BRIDGED HETEROCYCLIC COMPOUND, AND COMPOSITION AND APPLICATION THEREOF

-

Paragraph 0067, (2021/11/04)

Provided are an acylamino bridged heterocyclic compound of formula (I) or a pharmaceutically acceptable salt, an isomer, a solvate, a crystal, or a prodrug thereof, and a pharmaceutical composition comprising the compound, and an application of the compou

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

Wu, Xiaofang,Zhou, Lei,Li, Fangshao,Xiao, Jing

, p. 491 - 497 (2021/01/20)

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

Bobal, Pavel,Otevrel, Jan,Svestka, David

, p. 25029 - 25045 (2020/07/14)

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF

-

Paragraph 0375-0376, (2020/07/07)

It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

Greenhalgh, Mark D.,Laina-Martín, Víctor,Neyyappadath, Rifahath M.,Qu, Shen,Smith, Andrew D.,Smith, Samuel M.

supporting information, p. 16572 - 16578 (2020/09/09)

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids

Shao, Ying,Sun, Jiangtao,Tang, Shengbiao,Wang, Kai,Yu, Jianliang

supporting information, p. 23516 - 23520 (2020/10/21)

The asymmetric synthesis of β2,2-amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2-amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to β2,2-amino acids has been developed.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

Wu, Xiaofang,Zhou, Lei,Yang, Ruoqi,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing

, p. 301 - 304 (2020/01/29)

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

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