20618-42-2

Basic information

• Product Name: 2-(hydroxyMethyl)cyclopentanone
• Synonyms: 2-(hydroxyMethyl)cyclopentanone
• CAS NO: 20618-42-2
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.1424
• Mol File: 20618-42-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(hydroxyMethyl)cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(hydroxyMethyl)cyclopentanone(20618-42-2)
• EPA Substance Registry System: 2-(hydroxyMethyl)cyclopentanone(20618-42-2)

Safety Data

• Hazardous Substances Data: 20618-42-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(Hydroxymethyl)cyclopentanone is used as an active ingredient in the production of pharmaceuticals for its beneficial properties and pleasant aroma, contributing to the development of medications with improved patient compliance.
Used in Perfumery:
In the perfume industry, 2-(hydroxyMethyl)cyclopentanone is used as a fragrance ingredient due to its sweet, floral scent, enhancing the olfactory profile of various perfumes and colognes.
Used in Flavorings:
2-(Hydroxymethyl)cyclopentanone is employed as a flavoring agent in the food and beverage industry, adding a unique and pleasant taste to products, thereby improving their sensory appeal.
Used as a Precursor in Organic Synthesis:
2-(Hydroxymethyl)cyclopentanone serves as a precursor in the synthesis of various organic compounds, playing a crucial role in the creation of new chemical entities with potential applications in different fields.
Used as a Solvent in Chemical Processes:
2-(hydroxyMethyl)cyclopentanone is utilized as a solvent in certain chemical processes, facilitating reactions and improving the efficiency of industrial operations.
Used as a Chemical Intermediate in Organic Synthesis:
2-(Hydroxymethyl)cyclopentanone is also used as a chemical intermediate in organic synthesis, enabling the production of a wide range of chemical products.
It is essential to handle 2-(hydroxyMethyl)cyclopentanone with care and adhere to safety guidelines to prevent any potential hazards associated with its use.

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 110295-58-4 1,4-dioxa-spiro[4.4]nonane-6-carboxylic acid methyl ester 
• 69618-32-2 2-hydroxycyclopentane-1-methanol 
• 23153-73-3 ethyl 1,4-dioxaspiro[4,4]nonane-6-carboxylate 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 50-00-0 formaldehyd 
• 120-92-3 cyclopentanone 
• 1883-85-8 cis-2-(hydroxymethyl)cyclopentanol 
• 14579-07-8 1-(trimethylsilyl)cyclopentene 
• 138380-10-6 ethyl (trimethylsilyloxy)methyl sulfide 
• 23153-74-4 (1,4-dioxa-spiro[4.4]non-6-yl)-methanol 

Downstream Products

• 175398-30-8 (S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentanone 
• 130733-88-9 2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentan-1-one 
• 68755-19-1 trans-2-hydroxycyclopentanemethanol cyclic phosphoric acid phenyl ester 
• 160081-15-2 (S)-2-({(S)-2-[2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-1-fluoro-eth-(E)-ylidene]-cyclopentanecarbonyl}-amino)-3-phenyl-propionic acid tert-butyl ester 
• 160030-58-0 (S)-2-({(R)-2-[2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-1-fluoro-eth-(E)-ylidene]-cyclopentanecarbonyl}-amino)-3-phenyl-propionic acid tert-butyl ester 
• 183182-18-5 (S)-2-({2-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-fluoro-eth-(Z)-ylidene]-cyclopentanecarbonyl}-amino)-3-phenyl-propionic acid tert-butyl ester 

Relevant articles and documents

Chemoselective, iron(ii)-catalyzed oxidation of a variety of secondary alcohols over primary alcohols utilizing H2O2 as the oxidant

A mild, iron-based catalyst system is presented that selectively oxidizes secondary alcohols to the corresponding hydroxy ketones in the presence of primary alcohols within 15 minutes at room temperature, utilizing H 2O2 as the oxidant.

Facile synthesis of unsaturated lactones via intramolecular Wittig reaction

The phosphoranes 3 formed from the reaction of a variety of keto alcohols 1 and (triphenylphosphoranylidene)ethenone 2 undergo intramolecular Wittig cyclization to afford the unsaturated lactones in moderate yields.

Z-Selective Horner-Wadsworth-Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CFC]-Pro-OH dipeptide isostere

The Horner-Wadsworth-Emmons reactions of 2-fluoro-2-diethylphosphonoacetic acid with 2-{[(triisopropylsilyl)oxy]methyl}cyclopentanone (2-TOM-cyclopentanone) using methylmagnesium chloride furnished the corresponding tetra-substituted fluoroolefin in a Z-selective manner (E/Z = 9:91). A facile synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CFC]-Pro-OH as a dipeptide isostere was achieved based on the Z-selective Horner-Wadsworth-Emmons reaction.

Synthesis of a novel bicyclic scaffold inspired by the antifungal natural product sordarin

A simplified bicyclic scaffold inspired by the antifungal natural product sordarin was designed and synthesized which maintains the carboxylic acid/aldehyde (or nitrile) pharmacophore. Docking studies with the target for sordarin, the fungal protein eukaryotic elongation factor 2 (eEF2), suggested that the novel scaffolds may bind productively. A densely functionalized chiral cyclopentadiene was constructed in 8 steps and utilized in a Diels-Alder reaction with acrylonitrile. The resulting [2.2.1] cycloheptene was transformed into a scaffold possessing vicinal carboxylic acid and nitrile groups, with orientations predicted to provide high affinity for eEF2. The synthetic approach disclosed here sets the stage for a renewed medicinal chemistry campaign against eEF2.

Synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols or 3-amino alcohols using iodobenzene dichloride and sodium azide

A general and efficient method for the synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols and 3-amino alcohols has been developed using the same reagent combination of iodobenzene dichloride (PhICl2) and sodium azide (NaN3).

Cathodic cyclisation of N-(oxoalkyl)pyridinium salts - Formation of tricyclic indolizidine and quinolizidine derivatives in aqueous medium

The cathodic cyclisation of N-(oxoalkyl)pyridinium salts, derived from 4-methylpyridine and cyclic ketones, afforded functionalised tricyclic indolizidine and quinolizidine derivatives in high yields. Through systematic variation of the ring size of the k

Baeyer-Villiger oxidations catalyzed by engineered microorganisms: Enantioselective synthesis of δ-valerolactones with functionalized chains

Cyclohexanone monooxygenase (CHMO) from Acinetobacter sp NCIMB 9871 expressed in baker's yeast and in E. coli and cyclopentanone monooxygenase (CPMO) from Comamonas (previously Pseudomonas) sp. NCIMB 9872 expressed in E. coli are new bioreagents for Baeye

Direct asymmetric α-hydroxylation of 2-hydroxymethyl ketones

A direct α-hydroxylation of racemic 2-hydroxymethyl ketones with the Sharpless epoxidation catalyst resulted in α,β-dihydroxy ketones in high ee (up to 97%) and in moderate to good isolated yield (up to 58%).

Selective Oxidation of Diols by H2O2/TS-1 System and by DMDO.

Selective oxidations of secondary hydroxyl groups vs. primary ones in 1,n-diols by TS-1/H2O2 catalitic system and by dimethyldioxirane, new reagents with low environmental pollution, are reported.

FLUOROOLEFIN PEPTIDE ISOSTERES - TOOLS FOR CONTROLLING PEPTIDE CONFORMATIONS

Fluoroolefin dipeptide isosteres were synthesized applying the Peterson reaction as a novel method for fluoroolefination.The dipeptide isosteres were elaborated to provide the conformationally constrained analogs (1-(R), 1-(S) and 2-(R), 2-(S)) of the Suc-Ala-Gly-Pro-Phe-pNA tetrapeptide, a synthetic substrate of cyclophilin.