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1-Phenyl-cyclopropanecarbonyl chloride, with the molecular formula C10H9ClO, is a chemical compound featuring a carbonyl chloride functional group (COCl) attached to a phenyl-cyclopropane ring. This highly reactive compound is known for its ability to participate in various chemical reactions, such as nucleophilic substitution and addition reactions, making it a versatile and valuable compound in organic chemistry.

63201-02-5

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63201-02-5 Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-cyclopropanecarbonyl chloride is used as an intermediate in the synthesis of various pharmaceuticals for its ability to undergo multiple chemical reactions, contributing to the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
1-PHENYL-CYCLOPROPANECARBONYL CHLORIDE is utilized in the manufacturing of agrochemicals, where its reactivity allows for the creation of various agricultural products that can enhance crop protection and yield.
Used in Dye Industry:
1-Phenyl-cyclopropanecarbonyl chloride is used as an intermediate in the production of dyes, where its chemical properties enable the synthesis of a wide range of colorants for various applications.
Used in Specialty Chemicals Industry:
It is also employed in the production of specialty chemicals, where its unique reactivity and properties are harnessed to create specific compounds for targeted applications.
Safety Note:
Due to its reactivity and potential for hazardous reactions, 1-Phenyl-cyclopropanecarbonyl chloride should be handled and stored with care in a controlled laboratory environment to ensure safety and proper use.

Check Digit Verification of cas no

The CAS Registry Mumber 63201-02-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,3,2,0 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 63201-02:
(7*6)+(6*3)+(5*2)+(4*0)+(3*1)+(2*0)+(1*2)=75
75 % 10 = 5
So 63201-02-5 is a valid CAS Registry Number.

63201-02-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-phenylcyclopropane-1-carbonyl chloride

1.2 Other means of identification

Product number -
Other names phenylcyclopropylcarboxylic 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:63201-02-5 SDS

63201-02-5Relevant articles and documents

Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation

Tng, Jiahui,Lim, Junxian,Wu, Kai-Chen,Lucke, Andrew J.,Xu, Weijun,Reid, Robert C.,Fairlie, David P.

supporting information, p. 5956 - 5971 (2020/06/05)

AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

Shi, Yongjia,Gao, Qian,Xu, Senmiao

supporting information, p. 10599 - 10604 (2019/08/28)

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

1,3-SUBSTITUED PYRAZOLE COMPOUNDS USEFUL FOR REDUCTION OF VERY LONG CHAIN FATTY ACIC LEVELS

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Paragraph 366, (2018/06/30)

Disclosed are chemical entities which are compounds of Formula (I) and pharmaceutically acceptable salts thereof, wherein Formula (I) has the structure: R1a, R1b, R2, R3, R4a, R4b and Y are as defined herein. These chemical entities are useful for reduction of very long chain fatty acid levels. These chemical entities and pharmaceutically acceptable compositions comprising such chemical entities can be useful for treating various diseases, disorders and conditions, such as adrenoleukodystrophy (ALD).

Synthesis of 4H-1,3-Benzoxazines via Metal- and Oxidizing Reagent-Free Aromatic C-H Oxygenation

Xu, Fan,Qian, Xiang-Yang,Li, Yan-Jie,Xu, Hai-Chao

supporting information, p. 6332 - 6335 (2017/12/08)

An unprecedented electrochemical aromatic C-H oxygenation reaction for the synthesis of 4H-1,3-benzoxazines from easily available N-benzylamides is reported. These oxidative cyclization reactions proceed in a transition metal- and oxidizing reagent-free fashion and produce H2 as only theoretical byproduct. Adapting the C-H oxygenation reaction in an electrochemical microreactor has been demonstrated.

Design, synthesis, and analysis of antagonists of GPR55: Piperidine-substituted 1,3,4-oxadiazol-2-ones

Meza-Avi?a, Maria Elena,Lingerfelt, Mary A.,Console-Bram, Linda M.,Gamage, Thomas F.,Sharir, Haleli,Gettys, Kristen E.,Hurst, Dow P.,Kotsikorou, Evangelia,Shore, Derek M.,Caron, Marc G.,Rao, Narasinga,Barak, Larry S.,Abood, Mary E.,Reggio, Patricia H.,Croatt, Mitchell P.

supporting information, p. 1827 - 1830 (2016/12/22)

A series of 1,3,4-oxadiazol-2-ones was synthesized and tested for activity as antagonists at GPR55 in cellular beta-arrestin redistribution assays. The synthesis was designed to be modular in nature so that a sufficient number of analogues could be rapidly accessed to explore initial structure–activity relationships. The design of analogues was guided by the docking of potential compounds into a model of the inactive form of GPR55. The results of the assays were used to learn more about the binding pocket of GPR55. With this oxadiazolone scaffold, it was determined that modification of the aryl group adjacent to the oxadiazolone ring was often detrimental and that the distal cyclopropane was beneficial for activity. These results will guide further exploration of this receptor.

Palladium(II)-Catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines

Chan, Kelvin S. L.,Fu, Hai-Yan,Yu, Jin-Quan

supporting information, p. 2042 - 2046 (2015/03/04)

C-H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C-H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C-H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.

ANTI-CANCER ACTIVITY OF NOVEL BICYCLIC HETEROCYCLES

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Paragraph 0765-0768, (2014/04/03)

The present invention relates to compound of formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, Formulas (I), (II), (III) and (IV) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1 or as described in detail in the description of the invention, and to the use of said compounds to treat or prevent proliferative disorders and their use to manufacture a medicine to treat or prevent proliferative disorders, particularly cancer such as leukemia. The present invention also relates to pharmaceutical compositions of said compounds and the use of said pharmaceutical compositions to treat or prevent proliferative disorders. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of proliferative disorders and pathologic conditions such as, but not limited to, cancer such as leukemia.

Structure-activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1

Egleton, James E.,Thinnes, Cyrille C.,Seden, Peter T.,Laurieri, Nicola,Lee, Siu Po,Hadavizadeh, Kate S.,Measures, Angelina R.,Jones, Alan M.,Thompson, Sam,Varney, Amy,Wynne, Graham M.,Ryan, Ali,Sim, Edith,Russell, Angela J.

, p. 3030 - 3054 (2014/05/20)

A naphthoquinone inhibitor of human arylamine N-acetyltransferase 1 (hNAT1), a potential cancer biomarker and therapeutic target, has been reported which undergoes a distinctive concomitant color change from red to blue upon binding to the enzyme. Here we describe the use of in silico modeling alongside structure-activity relationship studies to advance the hit compound towards a potential probe to quantify hNAT1 levels in tissues. Derivatives with both a fifty-fold higher potency against hNAT1 and a two-fold greater absorption coefficient compared to the initial hit have been synthesized; these compounds retain specificity for hNAT1 and its murine homologue mNat2 over the isoenzyme hNAT2. A relationship between pKa, inhibitor potency and colorimetric properties has also been uncovered. The high potency of representative examples against hNAT1 in ZR-75-1 cell extracts also paves the way for the development of inhibitors with improved intrinsic sensitivity which could enable detection of hNAT1 in tissue samples and potentially act as tools for elucidating the unknown role hNAT1 plays in ER+ breast cancer; this could in turn lead to a therapeutic use for such inhibitors.

Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles

Salikov, Rinat F.,Platonov, Dmitry N.,Frumkin, Aleksandr E.,Lipilin, Dmitry L.,Tomilov, Yury V.

, p. 3495 - 3505 (2013/04/23)

2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3- dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity.

Palladium(0)-catalyzed enantioselective C-H arylation of cyclopropanes: Efficient access to functionalized tetrahydroquinolines

Saget, Tanguy,Cramer, Nicolai

supporting information, p. 12842 - 12845 (2013/02/22)

Activated: The title reaction proceeds efficiently with 1 mol % of palladium and gives tetrahydroquinolines in excellent enantioselectivities (see scheme). The enantiodiscriminating concerted metalation-deprotonation step occurs via a rare seven-membered palladacycle. The cyclopropyl-substituted tetrahydroquinolines can be regioselectively and enantiospecifically reduced to chiral tetrahydrobenzoazepines. Copyright

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