Production Method 1

872-53-7

Reaction Conditions

1.1 Reagents: Triphenyl phosphite ,  Hydrogen Catalysts: (SP-4-2)-(2,4-Pentanedionato-κO2,κO4)bis(triphenyl phosphite-κP)rhodium

Reference

The hydroformylation reaction

Ojima, Iwao; et al, Organic Reactions (Hoboken, 2000, 56,

Production Method 2

872-53-7

Reaction Conditions

1.1 Reagents: Alumina ,  Lithium bromide Solvents: Toluene ;  reflux

Reference

Lithium bromide

Charette, Andre B., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2006, 1, 1-4

Production Method 3

872-53-7

Reaction Conditions

1.1 Catalysts: Lithium bromide

Reference

A convenient synthesis of aldehydes by rearrangement of cyclic epoxides with lithium bromide on alumina

Suga, Hisashi; et al, Synthesis, 1988, (5), 394-5

Production Method 4

32122-32-0

872-53-7

Reaction Conditions

1.1 Solvents: Formic acid

Reference

Preparation of cyclopentylmethanal and application to different syntheses

De Botton, Marcel, Comptes Rendus des Seances de l'Academie des Sciences, 1971, 272(1), 118-21

Production Method 5

32122-32-0

872-53-7

Reaction Conditions

1.1 Reagents: Formic acid

Reference

Reaction of ethoxymethylmagnesium chloride with cyclanones. I. Preparation of formylcyclanes

De Botton, Marcel, Bulletin de la Societe Chimique de France, 1975, 1773, 1773-6

Production Method 6

3400-45-1

872-53-7

Reaction Conditions

1.1 Reagents: Aluminum hydride Solvents: Tetrahydrofuran
1.2 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane

Reference

Conversion of carboxylic acids into aldehydes by oxidation of alkoxyaluminum intermediate with pyridinium chlorochromate or pyridinium dichromate

Cha, Jin Soon; et al, Bulletin of the Korean Chemical Society, 1998, 19(7), 730-732

Production Method 7

6140-65-4

872-53-7

Reaction Conditions

1.1 Reagents: Cuprate(1-), hydro-1-pentynyl-, lithium Solvents: Tetrahydrofuran

Reference

Organocopper reagents: substitution, conjugate addition, carbo/metallocupration, and other reactions

Lipshutz, Bruce H.; et al, Organic Reactions (Hoboken, 1992, 41,

Production Method 8

70341-45-6

872-53-7

Reaction Conditions

1.1 Reagents: Benzenemethanaminium, N,N,N-trimethyl-, hydrogen tetradeca-μ-oxotetra-μ3-oxodi-μ… Catalysts: p-Toluenesulfonic acid ;  1 min, rt

Reference

Rapid and efficient method for room temperature deoximation reaction under solvent-free conditions

Dewan, Anindita; et al, Bulletin of the Korean Chemical Society, 2011, 32(7), 2482-2484

Production Method 9

872-53-7

Reaction Conditions

1.1 Reagents: Thallium nitrate Solvents: Methanol

Reference

Thallium in organic synthesis. XX. Oxidative rearrangement of olefins with thallium(III) nitrate: simple one-step synthesis of aldehydes and ketones

McKillop. Alexander; et al, Tetrahedron Letters, 1970, (60), 5275-80

Production Method 10

872-53-7

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Mercuric sulfate Solvents: Water

Reference

Synthesis of some δ-lactones of α,β,δ-trihydroxy acids

English, James Jr.; et al, Journal of the American Chemical Society, 1951, 73, 615-18

Production Method 11

2591-86-8

33240-34-5

872-53-7

Reaction Conditions

Reference

Synthesis methods and reactions. 102. Aldehydes by formylation of Grignard and organolithium reagents with N-formylpiperidine

Olah, George A.; et al, Angewandte Chemie, 1981, 93(10), 925-6

Production Method 12

872-53-7

Reaction Conditions

1.1 Catalysts: Triphenyl phosphite ,  Dicarbonylrhodium acetylacetonate Solvents: Acetone ;  5 min, rt
1.2 Reagents: Hydrogen ;  72 h, 20 bar, 40 °C; 40 °C → rt

Reference

Tandem metal and organocatalysis in sequential hydroformylation and enantioselective Mannich reactions

Chercheja, Serghei; et al, Advanced Synthesis & Catalysis, 2009, 351(3), 339-344

Production Method 13

872-53-7

Reaction Conditions

1.1 Catalysts: Methanesulfonic acid, 1,1,1-trifluoro-, erbium(3+) salt (3:1) Solvents: Dichloromethane ;  5 h, reflux

Reference

Erbium(III) triflate: A valuable catalyst for the rearrangement of epoxides to aldehydes and ketones

Procopio, Antonio; et al, Synlett, 2004, (14), 2633-2635

Production Method 14

3637-61-4

872-53-7

Reaction Conditions

1.1 Reagents: Ceria ,  Gold ;  8 h, 150 °C

Reference

Maximizing the Number of Interfacial Sites in Single-Atom Catalysts for the Highly Selective, Solvent-Free Oxidation of Primary Alcohols

Li, Tianbo; et al, Angewandte Chemie, 2018, 57(26), 7795-7799

Production Method 15

3637-61-4

872-53-7

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Oxygen Catalysts: Phenylacetylene (azidated, reaction products with silanes and complexes with palladium …) ,  Iron oxide (Fe3O4) ,  Glycidoxypropyltrimethoxysilane (azide-linked with phenylacetylene and complexes with palladium chlorid…) ,  Silica ,  Palladium chloride Solvents: Water ;  12 h, 1 atm, 80 °C

Reference

Green and selective oxidation of alcohols by immobilized Pd onto triazole functionalized Fe3O4 magnetic nanoparticles

Dadras, Arefeh; et al, Journal of Chemical Sciences (Berlin, 2018, 130(12), 1-10

Production Method 16

20117-79-7

872-53-7

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Water-d2 Catalysts: Gallate(12-), hexakis[μ-[[N,N′-1,5-naphthalenediylbis[2,3-di(hydroxy-κO)benzamid… Solvents: Water ;  6 h, pH 10, 50 °C

Reference

Catalytic deprotection of acetals in basic solution with a self-assembled supramolecular "nanozyme"

Pluth, Michael D.; et al, Angewandte Chemie, 2007, 46(45), 8587-8589

Production Method 17

3400-45-1

872-53-7

Reaction Conditions

1.1 Reagents: (T-4)-Chlorohydro(1,1,2-trimethylpropyl)[1,1′-thiobis[methane]]boron Solvents: Dichloromethane

Reference

Exceptionally facile reduction of acyclic and alicyclic carboxylic acids to aldehydes by thexylchloroborane-dimethyl sulfide

Brown, Herbert C.; et al, Journal of the American Chemical Society, 1984, 106(25), 8001-2

Production Method 18

3400-45-1

872-53-7

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C
1.2 Reagents: Water ;  cooled
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  2 h, rt
2.2 Reagents: Sodium thiosulfate Solvents: Water ;  30 min, rt

Reference

Organocatalytic alkylation and photoorganocatalyst-free acylation of azomethine imines by Hantzsch esters under blue LED light

Li, Jiacheng; et al, New Journal of Chemistry, 2023, 47(42), 19421-19427

Production Method 19

70080-08-9

872-53-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Water Solvents: Water

Reference

Phosphonate reagents for the synthesis of enol ethers and one-carbon homologation to aldehydes

Kluge, Arthur F.; et al, Journal of Organic Chemistry, 1979, 44(26), 4847-52

Production Method 20

23985-40-2

3561-67-9

872-53-7

Reaction Conditions

1.1 Reagents: Butyllithium ;  -30 °C
1.2 Reagents: Hydrogen peroxide Solvents: Water

Reference

Formation of carbon-carbon and carbon-heteroatom bonds via organoboranes and organoborates

Negishi, Ei-Ichi; et al, Organic Reactions (Hoboken, 1985, 33,

Production Method 21

36601-82-8

872-53-7

Reaction Conditions

1.1 Reagents: Silica ;  7 min

Reference

A facile method for the conversion of oximes and tosylhydrazones to carbonyl compounds with Cr-MCM-41 zeolite under microwave irradiation

Nagarapu, Lingaiah; et al, Synthetic Communications, 2002, 32(14), 2195-2202

Production Method 22

3814-30-0

872-53-7

Reaction Conditions

1.1 Reagents: Dimethyl sulfoxide ,  Sodium bicarbonate ;  240 s

Reference

Aliphatic aldehydes synthesis from halides by Kornblum's reaction using a new fast method

Bratulescu, George, Revista de Chimie (Bucharest, 2010, 61(8), 815-816

Production Method 23

70341-45-6

872-53-7

Reaction Conditions

1.1 Reagents: Silica ;  8 min

Reference

A facile method for the conversion of oximes and tosylhydrazones to carbonyl compounds with Cr-MCM-41 zeolite under microwave irradiation

Nagarapu, Lingaiah; et al, Synthetic Communications, 2002, 32(14), 2195-2202

Production Method 24

872-53-7

Reaction Conditions

1.1 Reagents: (T-4)-Trifluoro[(iodosyl-κO)benzene]boron Solvents: Dichloromethane

Reference

Ring contraction in the reactions of cyclic olefins with reagents containing iodine(II)

Zefirov, N. S.; et al, Izvestiya Akademii Nauk SSSR, 1988, (6), 1452-3

Production Method 25

872-53-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Hexane ;  -78 °C; 10 min, -78 °C; 2 h, rt
1.2 Reagents: Methanol ;  30 min, rt
1.3 Catalysts: Perchloric acid ;  18 h, rt
1.4 Solvents: Diethyl ether
1.5 Reagents: Sodium bicarbonate Solvents: Water

Reference

Intramolecular regioselective addition of radicals and carbanions to ynol ethers. A strategy for the synthesis of exocyclic enol ethers

Hanna, Rana; et al, Tetrahedron, 2011, 67(1), 92-99

Production Method 26

2591-86-8

33240-34-5

872-53-7

Reaction Conditions

Reference

Aliphatic and alicyclic aldehydes: synthesis by C1-extension of organometallics

Hashmi, A. S. K., Science of Synthesis, 2007, 25, 337-353

Production Method 27

33240-34-5

872-53-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

Synthetic methods and reactions; part 109. Improved preparation of aldehydes and ketones from N,N-dimethylamides and Grignard reagents

Olah, George A.; et al, Synthesis, 1984, (3), 228-30

Cyclopentanecarboxaldehyde Raw materials

• Cyclopentanecarboxylic acid
• cyclopentylmethanol
• CYCLOPENTANECARBOXALDEHYDE, OXIME
• Cyclopentanol, 1-(ethoxymethyl)-
• Borane, tricyclopentyl-
• cyclopent-1-ene-1-carbaldehyde
• piperidine-1-carbaldehyde
• (Bromomethyl)cyclopentane
• Bromocyclopentylmagnesium (2.0\xa0M Solution in Diethyl Ether)
• Bis(phenylthio)methane
• Cyclopentane, (dimethoxymethyl)-
• 2-(Cyclopentylidenemethoxy)tetrahydro-2H-pyran
• Benzenesulfonic acid, 4-methyl-, 2-(cyclopentylmethylene)hydrazide

Cyclopentanecarboxaldehyde Preparation Products

• Cyclopentanecarboxaldehyde (872-53-7)

• 1. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 2. Excitonic channels from bio-inspired templated supramolecular assembly of J-aggregate nanowires?
  Daniel Messmer,Stefan Salentinig,Jakob Heier Nanoscale, 2019,11, 6929-6938
• 3. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 4. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 5. Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organic oxides Organic oxides
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organic oxides
• Solvents and Organic Chemicals Organic Compounds Aldehyde/Ketone

Introduction to Cyclopentanecarboxaldehyde (CAS No. 872-53-7)

Cyclopentanecarboxaldehyde, with the chemical formula C₇H₁₀O, is a significant compound in the field of organic chemistry and pharmaceutical research. This aldehyde derivative is characterized by a cyclopentane ring substituted with a formyl group, making it a versatile intermediate in synthetic chemistry. The compound's unique structural properties have garnered considerable attention from researchers due to its potential applications in drug development and material science.

The synthesis of Cyclopentanecarboxaldehyde can be achieved through various methods, including oxidation of cyclopentanol or formylation of cyclopentane derivatives. Advanced techniques such as Vilsmeier-Haack formylation have been employed to enhance yield and purity, ensuring the compound meets the stringent requirements of modern pharmaceutical applications. The compound's reactivity makes it a valuable building block for constructing more complex molecules, particularly in the synthesis of heterocyclic compounds and natural product analogs.

In recent years, Cyclopentanecarboxaldehyde has been extensively studied for its role in medicinal chemistry. Its aldehyde functionality allows for facile derivatization into esters, amides, and other pharmacophores, which are critical for designing novel therapeutic agents. For instance, researchers have explored its use in developing inhibitors targeting enzyme cascades involved in inflammatory diseases. Preliminary studies suggest that derivatives of this compound exhibit promising anti-inflammatory properties by modulating key signaling pathways.

The compound's significance extends beyond pharmaceuticals into the realm of materials science. Researchers have investigated its potential as a precursor for high-performance polymers and coatings. The cyclopentane ring's rigidity contributes to the enhanced thermal stability of resulting materials, making them suitable for applications in harsh environments. Additionally, the aldehyde group provides reactive sites for cross-linking and polymerization, enabling the creation of novel composite materials with tailored properties.

Recent advancements in computational chemistry have further highlighted the utility of Cyclopentanecarboxaldehyde. Molecular modeling studies have revealed its interactions with biological targets at an atomic level, aiding in the rational design of drug candidates. These simulations have been instrumental in predicting binding affinities and optimizing lead compounds for clinical trials. The integration of machine learning algorithms has accelerated this process, allowing for rapid screening of potential derivatives with enhanced efficacy.

The environmental impact of synthesizing and utilizing Cyclopentanecarboxaldehyde has also been a focus of recent research. Green chemistry principles have been applied to develop more sustainable synthetic routes, minimizing waste and reducing energy consumption. Catalytic processes employing recyclable materials have been explored to enhance efficiency while adhering to ecological standards. Such innovations align with global efforts to promote sustainable practices in chemical manufacturing.

In conclusion, Cyclopentanecarboxaldehyde (CAS No. 872-53-7) represents a cornerstone in modern chemical research. Its broad applicability in pharmaceuticals and materials science underscores its importance as a synthetic intermediate. As research continues to uncover new methodologies and applications, this compound is poised to play an even greater role in advancing scientific and industrial progress.

• 1271-48-3(FcDc)
• 12093-10-6(Ferrocenecarboxaldehyde)
• 765288-09-3(Cyclopentaneacetaldehyde,2-formyl-, (1R,2S)-)
• 6283-42-7(CYCLOPENTANEACETALDEHYDE, 2-FORMYL-A,3-DIMETHYL)
• 550-45-8((1R,2S,5R)-2-methyl-5-[(2R)-1-oxopropan-2-yl]cyclopentanecarbaldehyde)
• 84604-58-0(Cyclopentanecarboxaldehyde,2-pentyl-)
• 17206-62-1(2-methylcyclopentane-1-carbaldehyde)
• 124615-11-8(Cyclopentanecarboxaldehyde,3-(1-methylethyl)- (9CI))
• 20106-44-9(Cyclopentanecarboxaldehyde, 2-methyl-, trans-)
• 4750-17-8(1,3-Cyclopentanedicarboxaldehyde)