2158-31-8

Basic information

• Product Name: CYCLOHEPTANONE OXIME
• Synonyms: CYCLOHEPTANONE OXIME;SUBEROXIME;N-cycloheptylidenehydroxylamine
• CAS NO: 2158-31-8
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18
• Mol File: 2158-31-8.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 152 °C / 20mmHg
• Flash Point: 127.5°C
• Appearance: /
• Density: 1,03 g/cm3
• Refractive Index: 1.5010-1.5040
• Merck: 14,2722
• CAS DataBase Reference: CYCLOHEPTANONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEPTANONE OXIME(2158-31-8)
• EPA Substance Registry System: CYCLOHEPTANONE OXIME(2158-31-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2158-31-8(Hazardous Substances Data)

Usage

General Description

Cycloheptanone oxime, also known as 2-cycloheptanone oxime, is a chemical compound with the molecular formula C7H13NO. It is a colorless to pale yellow liquid with a faint odor and is commonly used in the synthesis of various pharmaceuticals and organic compounds. Cycloheptanone oxime has been found to exhibit antioxidant and antimicrobial properties, making it useful in the formulation of personal care products and cosmetic formulations. It is also used as a chelating agent in metal ion removal and as a reagent in organic chemical reactions. Additionally, it is a precursor in the synthesis of heterocyclic compounds and has potential applications in the development of new materials and chemicals.

Upstream product

• 502-42-1 cycloheptanone 
• 5452-35-7 cycloheptanamine 
• 546-88-3 acetylhydroxamic acid 
• 628-92-2 Cycloheptene 
• 505-48-6 octane-1,8-dioic acid 
• 502-41-0 cycloheptanol 
• 291-64-5 cycloheptane 
• 107092-99-9 1-Hydroxyamino-cycloheptanol 
• 36291-53-9 1-nitro-1-cycloheptene 
• 2562-40-5 nitrocycloheptane 
• 3238-19-5 2-chlorocycloheptanone oxime 

Downstream Products

• 502-42-1 cycloheptanone 
• 26228-96-6 3,3-dichlorohexahydroazocin-2(1H)-one 
• 3349-73-3 cycloheptanone 2,4-dinitrophenylhydrazone 
• 132644-70-3 4,5-endo-bis(phenylsulfonyl)-7-oxa-1-azabicyclo<2.2.1>heptane-2-spiro-1'-cycloheptane 
• 19731-72-7 Cycloheptanonoxim-O-benzylaether 
• 34768-70-2 C₁₇H₂₈N₂O₂ 
• 22928-63-8 1-aza-2-cyclooctanthione 
• 5452-35-7 cycloheptanamine 
• 673-66-5 7-amino-heptanoic acid lactam 
• 1121-92-2 heptamethyleneimine 
• 109473-46-3 cycloheptanone-(O-picryl oxime ) 
• 7664-41-7 ammonia 
• 174186-17-5 Cycloheptanone O-(2-nitrophenyl)oxime 

Relevant articles and documents

Asymmetric meso-CF3-BODIPY dyes based on cycloalkanopyrroles

New meso-CF3-substituted BODIPY derivatives have been synthesized using the methodology that includes as a key step the condensation of pyrroles with trifluoro(2,3-cycloalkanopyrrol-2-yl)ethanols. The further reaction of dipyrromethanes thus obtained with DDQ followed by complexation with BF3 leads to either benzo[b]-fused (in the case of dipyrromethanes obtained from trifluoro(4,5,6,7-tetrahydroindol-2-yl)ethanol) or cycloheptano[b]-fused saturated or partially saturated BODIPY dyes. The latter exhibit strong red fluorescence (λem = 588–634 nm, Φf = 0.54–0.68), while benzo[b]-fused do not fluoresce at all in either polar or non-polar solvents. The performed quantum-chemical calculations (TD-CAM-B3LYP/SVP) explain the spectroscopic results.

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine

O-Unprotected keto-and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.

Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones

Carbon-carbon bond formation is among the most important reactions in organic synthesis. Reconstruction of a carbon-carbon bond through ring-opening C-C bond cleavage of a strained carbocycle usually occurs via a thermodynamically preferable pathway. However, carbon-carbon bond formation through thermodynamically less favorable C-C bond cleavage has seldom been documented. Herein, we disclose an unusual C-C bond cleavage of cycloketone oxime esters for [4+1] annulation. Under anaerobic copper(I) catalysis, cycloketone oxime esters underwent regioselective, thermodynamically less favorable radical C-C bond cleavage followed by annulation with enaminothiones; that is, α-thioxo ketene N,S-acetals efficiently affording 2-cyanoalkyl-aminothiophene derivatives. Cyclobutanone, -pentanone, -hexanone, and -heptanone oxime esters could act as the effective C1 building blocks in the annulation reaction. An iminyl radical mechanism is proposed for the rare C-C bond cleavage/[4+1] annulation cascade.