6688-11-5

Basic information

• Product Name: Cyclooctanecarbaldehyde
• Synonyms: CYCLOOCTANECARBALDEHYDE;CYCLOOCTANECARBOXALDEHYDE;RARECHEM AK ML 0064;Formylcyclooctane.;Cyclooctane-1-carbaldehyde;Ai3-39192;Einecs 229-732-0;CYCLOOCTANECARBALDEHYDE HYDRATE
• CAS NO: 6688-11-5
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• EINECS: 229-732-0
• Mol File: 6688-11-5.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 199-200°C
• Flash Point: 67.2 °C
• Appearance: /
• Density: 0.9271
• Vapor Pressure: 0.227mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: Cyclooctanecarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclooctanecarbaldehyde(6688-11-5)
• EPA Substance Registry System: Cyclooctanecarbaldehyde(6688-11-5)

Safety Data

• Hazard Codes: Xn
• Statements: 10-36/37/38-36-22
• Safety Statements: 16-26-36
• RIDADR: 1989
• Hazardous Substances Data: 6688-11-5(Hazardous Substances Data)

Usage

General Description

Cyclooctanecarbaldehyde, also known as cyclooctane-1-carbaldehyde, is a chemical compound with the molecular formula C8H14O. It is a colorless liquid with a strong, unpleasant odor and is insoluble in water. Cyclooctanecarbaldehyde is commonly used in the production of fragrances, flavors, and pharmaceuticals. It is also utilized as a precursor in the synthesis of various organic compounds and as a reagent in organic chemistry. Despite its potential uses, cyclooctanecarbaldehyde is considered to be hazardous, as it can cause irritation to the skin, eyes, and respiratory system upon exposure. It is important to handle and store this chemical with care and follow proper safety protocols to prevent potential health risks.

InChI:InChI=1/C9H16O/c10-8-9-6-4-2-1-3-5-7-9/h8-9H,1-7H2

Upstream product

• 931-88-4 cis-Cyclooctene 
• 1633-64-3 (Z)-2-chlorocyclooct-1-ene-1-carbaldehyde 
• 50-00-0 formaldehyd 
• 931-88-4 1,2-cyclooctene 
• 64-18-6 formic acid 
• 502-49-8 cycloactanone 
• 68-12-2 N,N-dimethyl-formamide 
• 201230-82-2 carbon monoxide 
• 3637-63-6 cyclooctylmethanol 
• 73039-86-8 2-Carbomethoxy-1-oxaspiro<2,7>decane 
• 62034-88-2 cyclooctyl carboxaldehyde dimethyl acetal 
• 20653-55-8 1-Hydroxy-1-aethoxymethyl-cyclooctan 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 104563-24-8 Sodium; 1-oxa-spiro[2.7]decane-2-carboxylate 

Downstream Products

• 109277-39-6 (5S,6R)-5-Benzyl-6-cyclooctyl-dihydro-pyran-2,4-dione 
• 3637-63-6 cyclooctylmethanol 
• 109277-59-0 1-(1-Cyclooctyl-indan-2-yl)-ethanone 
• 674475-59-3 8-cyclooctylmethyl-1-(4-fluorophenyl)-(R)-3-oxinarylmethyl-1,3,8-triazaspiro[4.5]decan-4-one 
• 512177-16-1 4-acetyl-5-cyclooctyl-3-hydroxy-1-(4-methylphenyl)-1,5-dihydro-2H-pyrrol-2-one 
• 931-88-4 1,2-cyclooctene 
• 3724-54-7 methyl cyclooctanecarboxylate 
• 1291103-57-5 1-cyclooctyl-2-propynyl pentafluorobenzoate 
• 1291103-71-3 N-(1-cyclooctyl-2-propynyl)-N-methylaniline 
• 217461-40-0 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one 
• 69294-33-3 4-[(cyclooctylmethyl)amino]benzoic acid 
• 674477-21-5 8-cyclooctylmethyl-1-(4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one 
• 57230-13-4 cyclooctylethanolamine 
• 125335-08-2 1-phenylthiocyclo-octylmethanol 

Relevant articles and documents

Kinetics of cyclooctene hydroformylation for continuous homogeneous catalysis

The kinetics of Rh-catalysed cyclooctene hydroformylation were investigated, based on the mechanism described for a single tris(2,4-di-tert- butylphenyl)phosphite ligand coordinated to a rhodium center. The rate limiting step was found to be the coordination of cyclooctene to the metal center as suggested in literature. Parameters of the corresponding rate equation were estimated by nonlinear regression. Experimental data obtained from semi-batch reactions were compared with model predictions and shown to be in good agreement. A continuous jet-loop reactor with coupled nanofiltration was designed and the kinetics were validated. The Royal Society of Chemistry.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Determining the necessity of phenyl ring π-character in warfarin

Despite the difficulty in administering a safe dose regimen and reports of emerging resistance, warfarin (1) remains the most widely-used oral anticoagulant for the prevention and treatment of thrombosis in humans globally. Systematic substitution of the warfarin phenyl ring with either 1,3,5,7-cyclooctatetraene (COT) (2), cubane (3), cyclohexane (4) or cyclooctane (5) and subsequent evaluation against the target enzyme, vitamin K epoxide reductase (VKOR), facilitated interrogation of both steric and electronic properties of the phenyl pharmacophore. The tolerance of VKOR to further functional group modification (carboxylate 14, PTAD adduct 15) was also investigated. The results demonstrate the importance of both annulene conferred π-interactions and ring size in the activity of warfarin.