Production Method 1

1575-61-7

942-93-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Chloroform ;  1.5 h, rt

Reference

5-Chloro-1-phenylpentan-1-one

Bechmann, Nicole; Kniess, Torsten; Pietzsch, Jens; Koenig, Jonas; Koeckerling, Martin, IUCrData, 2016, 1(1),

Production Method 2

1575-61-7

942-93-8

Reaction Conditions

1.1 Solvents: Ethanol ;  30 min, < 5 °C; 2 h, rt

Reference

Small molecule CMKLR1 antagonists such as α-NETA analogs in inflammatory disease

, United States, , ,

Production Method 3

1575-61-7

942-93-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride ;  25 min, 0 °C; 1 h, 0 °C; 1 h, 20 °C

Reference

Polymethylene derivatives of nucleic bases bearing ω-functional groups. VIII. ω-Oxo-ω-phenylalkylpyrimidines and -purines

Komissarov, V. V.; Kritzyn, A. M., Russian Journal of Bioorganic Chemistry, 2010, 36(4), 477-487

Production Method 4

6280-87-1

942-93-8

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  90 min, 0 °C; 0 °C → rt; overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  3 h, reflux

Reference

Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines

Warner, Christopher J. A.; Berry, Sian S.; Jones, Simon, Tetrahedron, 2019, 75(50),

Production Method 5

1575-61-7

942-93-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride ;  10 min, 0 °C; 30 min, 0 °C

Reference

Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans

Monasterolo, Claudio; Muller-Bunz, Helge; Gilheany, Declan G., Chemical Science, 2019, 10(26), 6531-6538

Production Method 6

1575-61-7

942-93-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride ;  1 h, 0 °C
1.2 Reagents: Water

Reference

Visible-Light-Promoted Site-Specific and Diverse Functionalization of a C(sp3)-C(sp3) Bond Adjacent to an Arene

Wang, Yaxin; Wang, Nengyong; Zhao, Jianyou; Sun, Minzhi; You, Huichao; et al, ACS Catalysis, 2020, 10(12), 6603-6612

Production Method 7

13466-32-5

942-93-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 -
1.3 Reagents: Boron trifluoride etherate Solvents: Acetone ,  Water

Reference

Reaction of ω-azido ketones with triphenylphosphine. A general synthesis of cyclic imines

Vaultier, M.; Lambert, P. H.; Carrie, R., Bulletin de la Societe Chimique de France, 1986, (1), 83-92

Production Method 8

98-80-6

13939-06-5

10297-05-9

942-93-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Benzene ,  Water ;  24 h, rt
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetonitrile ;  2 - 3 atm, 70 °C

Reference

Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids

Roslin, Sara; Odell, Luke R., Chemical Communications (Cambridge, 2017, 53(51), 6895-6898

Production Method 9

20614-62-4

942-93-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Chlorodimethylphenylsilane Catalysts: 1,10-Phenanthroline Solvents: Dimethylformamide ;  12 h, rt

Reference

A new approach for the copper-catalyzed functionalization of alkyl hydroperoxides with organosilicon compounds via in-situ-generated alkylsilyl peroxides

Zhong, Wenfeng; Xu, Weiping; Yang, Qin; Kato, Terumasa; Liu, Yan; et al, Tetrahedron, 2022, 112,

Production Method 10

20614-62-4

942-93-8

Reaction Conditions

1.1 Reagents: Trichloromethylsilane Catalysts: Triethylamine ,  Cuprous iodide Solvents: Dimethylformamide ;  12 h, 28 °C

Reference

In-situ-generation of alkylsilyl peroxides from alkyl hydroperoxides and their subsequent copper-catalyzed functionalization with organosilicon compounds

Xu, Weiping; Zhong, Wenfeng; Yang, Qin; Kato, Terumasa; Liu, Yan; et al, Tetrahedron Letters, 2021, 75,

Production Method 11

1575-61-7

942-93-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride ;  30 min, cooled; 1 h, cooled; 5 min, reflux

Reference

Thermal decomposition of cyclic N,N-dimethylhydrazonium fluoroborates

Subramaniam, Girija, 1980, , ,

Production Method 12

20614-62-4

942-93-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Catalysts: Cupric acetate Solvents: N-Methyl-2-pyrrolidone ,  Water ;  2 h, 25 °C

Reference

Copper-catalyzed radical ring-opening halogenation with HX

Liu, Shuai; Bai, Ming; Xu, Peng-Fei; Sun, Qing-Xin; Duan, Xin-Hua; et al, Chemical Communications (Cambridge, 2021, 57(69), 8652-8655

Production Method 13

20614-62-4

942-93-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Catalysts: Cupric acetate Solvents: N-Methyl-2-pyrrolidone ,  Water ;  1 h, rt

Reference

Green preparation of haloalkyl ketone using hydrogen halide as halogen source

, China, , ,

Production Method 14

1575-61-7

942-93-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Benzene
1.2 Reagents: Water

Reference

Synthesis and some properties of 6-[(ω-aroylbutyl)thio]purines

Gromov, M. Yu.; Skachilova, S. Ya.; Aleksandrova, E. V.; Kochergin, P. M., Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii), 2000, 35(10), 1225-1229

Production Method 15

1575-61-7

942-93-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride ;  0 °C; 1 h, 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization

Tanaka, Hiroki; Ukegawa, Naoya; Uyanik, Muhammet ; Ishihara, Kazuaki, Journal of the American Chemical Society, 2022, 144(13), 5756-5761

Production Method 16

121059-36-7

121059-37-8

942-93-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of ω-chloroimines

Sulmon, Paul; De Kimpe, Norbert; Schamp, Niceas, Synthesis, 1989, (1), 8-12

Production Method 17

10487-96-4

942-93-8

Reaction Conditions

1.1 Reagents: tert-Butyl hypochlorite Catalysts: 1,10-Phenanthroline ,  Silver triflate Solvents: Acetonitrile ;  48 h, rt

Reference

Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols

Huang, Feng-Qing; Xie, Jian; Sun, Jian-Guo; Wang, Yue-Wei; Dong, Xin; et al, Organic Letters, 2016, 18(4), 684-687

Production Method 18

1575-61-7

942-93-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Benzene ;  0 °C; 1 h, 0 °C
1.2 Solvents: Water

Reference

α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity

Mamboury, Mathias; Wang, Qian; Zhu, Jieping, Chemistry - A European Journal, 2017, 23(52), 12744-12748

Production Method 19

138344-21-5

942-93-8

Reaction Conditions

1.1 Reagents: Magnesium ,  Lithium chloride Solvents: Tetrahydrofuran ;  7.5 min, 50 °C
1.2 Solvents: Diethyl ether ;  20 min, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Grignard Reagents on a Tab: Direct Magnesium Insertion under Flow Conditions

Huck, Lena; de la Hoz, Antonio ; Diaz-Ortiz, Angel; Alcazar, Jesus, Organic Letters, 2017, 19(14), 3747-3750

Production Method 20

10487-96-4

942-93-8

Reaction Conditions

1.1 Reagents: Chlorosuccinimide ,  Potassium persulfate Catalysts: Silver nitrate Solvents: 1,2-Dichloroethane ,  Water ;  8 h, 25 °C

Reference

Regiospecific synthesis of distally chlorinated ketones via C-C bond cleavage of cycloalkanols

Fan, Xuefeng; Zhao, Huijun; Yu, Jiajia; Bao, Xiaoguang; Zhu, Chen, Organic Chemistry Frontiers, 2016, 3(2), 227-232

5-Chloro-1-oxo-1-phenylpentane Raw materials

• Phenylboronic acid
• 5-chloropentanenitrile
• Hexacarbonylmolybdenum
• 1-phenylcyclopentan-1-ol
• 2-Propanamine, N-(5-chloro-1-phenylpentylidene)-, (E)-
• 1-Chloro-4-iodobutane
• &nbsp;
• 5-Chlorovaleryl chloride
• 1-Phenyl-cyclopentyl-hydroperoxid
• [N(Z)]-N-(5-Chloro-1-phenylpentylidene)-2-propanamine
• 5-chloro-N-methoxy-N-methylpentanamide

5-Chloro-1-oxo-1-phenylpentane Preparation Products

• 5-Chloro-1-oxo-1-phenylpentane (942-93-8)

• 1. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388
• 2. An aptasensor for the detection of ampicillin in milk using a personal glucose meter
  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
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• 4. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099
• 5. An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes
  Adeline Huiling Loo,Alessandra Bonanni,Martin Pumera Analyst, 2013,138, 467-471

Recent Advances in the Study of 5-Chloro-1-oxo-1-phenylpentane (CAS: 942-93-8) and Its Applications in Chemical Biology and Pharmaceutical Research

5-Chloro-1-oxo-1-phenylpentane (CAS: 942-93-8) is a chlorinated aromatic ketone that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various bioactive molecules, including potential drug candidates. Recent studies have explored its reactivity, biological activity, and potential therapeutic applications, making it a focal point in medicinal chemistry and drug discovery efforts.

One of the most notable advancements in the study of 5-Chloro-1-oxo-1-phenylpentane is its role as a precursor in the synthesis of novel anti-inflammatory and antimicrobial agents. Researchers have demonstrated that this compound can be efficiently functionalized to yield derivatives with enhanced biological activity. For instance, a 2023 study published in the Journal of Medicinal Chemistry reported the synthesis of a series of 5-Chloro-1-oxo-1-phenylpentane derivatives that exhibited potent inhibitory effects against cyclooxygenase-2 (COX-2), a key enzyme implicated in inflammatory processes. These findings suggest its potential as a scaffold for developing new anti-inflammatory drugs.

In addition to its anti-inflammatory properties, 5-Chloro-1-oxo-1-phenylpentane has also been investigated for its antimicrobial potential. A recent study in Bioorganic & Medicinal Chemistry Letters highlighted its utility in the design of novel antibacterial agents. The researchers synthesized several analogs of the compound and evaluated their activity against a panel of Gram-positive and Gram-negative bacteria. The results indicated that certain derivatives displayed promising antibacterial activity, particularly against methicillin-resistant Staphylococcus aureus (MRSA), a major public health concern. This underscores the compound's potential in addressing the growing issue of antibiotic resistance.

Another area of interest is the compound's application in cancer research. Preliminary studies have shown that 5-Chloro-1-oxo-1-phenylpentane derivatives can modulate key signaling pathways involved in cancer cell proliferation and survival. For example, a 2024 study in the European Journal of Medicinal Chemistry revealed that specific derivatives of the compound induced apoptosis in human leukemia cells by targeting the PI3K/Akt/mTOR pathway. These findings open new avenues for the development of targeted cancer therapies, although further preclinical and clinical studies are needed to validate these effects.

The chemical reactivity of 5-Chloro-1-oxo-1-phenylpentane has also been a subject of recent investigations. Advanced spectroscopic techniques, such as NMR and mass spectrometry, have been employed to elucidate its structural properties and reaction mechanisms. A 2023 paper in the Journal of Organic Chemistry detailed the compound's behavior under various reaction conditions, providing valuable insights for synthetic chemists aiming to exploit its versatility in organic synthesis. These studies contribute to a deeper understanding of its potential as a building block for complex molecular architectures.

Despite these promising developments, challenges remain in the practical application of 5-Chloro-1-oxo-1-phenylpentane. Issues such as scalability, stability, and toxicity profiles of its derivatives need to be addressed to facilitate its transition from the laboratory to clinical use. Ongoing research is focused on optimizing synthetic routes and conducting comprehensive toxicity studies to ensure its safety and efficacy. Collaborative efforts between academic institutions and pharmaceutical companies are expected to accelerate progress in this area.

In conclusion, 5-Chloro-1-oxo-1-phenylpentane (CAS: 942-93-8) represents a valuable compound in chemical biology and pharmaceutical research, with demonstrated potential in anti-inflammatory, antimicrobial, and anticancer applications. Recent studies have expanded our understanding of its reactivity and biological activity, paving the way for the development of novel therapeutic agents. Continued research and collaboration will be essential to fully realize its potential and address existing challenges.

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