874-23-7

Basic information

• Product Name: 2-ACETYLCYCLOHEXANONE
• Synonyms: alpha-Acetylcyclohexanone;2-Acetylcyclohexanone,98%;2-acetylcyclohexan-1-one;2-Acetylcyclohexanone,97%;2-ACETYLCYCLOHEXANONE FOR SYNTHESIS;2-Acetyl-1-cyclohexanone;2-acetyl-cyclohexanon;Acetylcyclohexanone
• CAS NO: 874-23-7
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.18
• EINECS: 212-858-5
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 874-23-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: -11°C
• Boiling Point: 111-112 °C18 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.078 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00189mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 10.91±0.20(Predicted)
• Water Solubility: Not miscible in water.
• BRN: 1858621
• CAS DataBase Reference: 2-ACETYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYLCYCLOHEXANONE(874-23-7)
• EPA Substance Registry System: 2-ACETYLCYCLOHEXANONE(874-23-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 874-23-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Different sources of media describe the Uses of 874-23-7 differently. You can refer to the following data:
1. 2-Acetylcyclohexanone is used in the synthesis of 1-(pyridyl)ethanol derivatives that can reduce keto-esters and ketones. Also used in the synthesis of phenothiazine derivatives that can inhibit prote in farnesyltransferase molecules and some that show anti-proliferative activity.
2. 2-Acetylcyclohexanone was used in the synthesis of anilinoethanolamines.

General Description

The keto-enol tautomerism of 2-acetylcyclohexanone (ACHE) in water was studied.

Purification Methods

Dissolve it in ligroin (b 30-60o), wash it with saturated aqueous NaHCO3, dry over Drierite and fractionate in a vacuum. [Perfetti & Levine J Am Chem Soc 75 626 1953, Manyik et al. J Am Chem Soc 75 5030 1953, Eistert & Reiss Chem Ber 87 108 1954.] It forms a Cu salt which crystallises in green leaflets from EtOH, m 162-163o [UV: McEntee & Pinder J Chem Soc 4419 1957].

InChI:InChI=1/C4H8O4/c5-3-4(6)8-2-1-7-3/h3-6H,1-2H2/t3-,4-/m0/s1

Upstream product

• 463-51-4 Ketene 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 108-94-1 cyclohexanone 
• 141-78-6 ethyl acetate 
• 75-36-5 acetyl chloride 
• 21173-96-6 1-(2-hydroxycyclohex-1-ene-1-yl)ethan-1-one 
• 15210-00-1 acide α-(ceto-2 cyclohexyle)-lactique 
• 7637-07-2 boron trifluoride 
• 108-24-7 acetic anhydride 
• 1424-22-2 1-cyclohexenyl acetate 
• 7664-93-9 sulfuric acid 
• 16111-92-5 1-(2-chloro-cyclohex-1-enyl)-ethanone 
• 40685-40-3 2-Methoxymethylen-cyclohexan-1-on 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 

Downstream Products

• 103796-40-3 4-methyl-5,6,7,8-tetrahydroquinazoline 
• 57205-12-6 2-Acetyl-2-phenylselenocyclohexanon 
• 102569-80-2 2-((E)-3-Furan-2-yl-acryloyl)-6-[1-furan-2-yl-meth-(E)-ylidene]-cyclohexanone 
• 107292-40-0 1-<2-<<2-(1H-Indol-3-yl)ethyl>amino>-1-cyclohexen-1-yl>ethanone 
• 107292-45-5 2-<1-<<2-(1H-Indol-3-yl)ethyl>amino>ethylidene>cyclohexanone 
• 17343-93-0 1,10-Di(α-cyclohexanone)decane-1,10-dione 
• 111239-44-2 (+)-2-acetyl-2-(2-methyl-2-propenyl)cyclohexanone 
• 111239-44-2 2-Acetyl-2-(2-methyl-allyl)-cyclohexanone 
• 102569-84-6 2-[(E)-3-(2,6-Dichloro-phenyl)-acryloyl]-6-[1-(2,6-dichloro-phenyl)-meth-(E)-ylidene]-cyclohexanone 
• 102569-91-5 2-[(E)-3-(4-Dimethylamino-phenyl)-acryloyl]-6-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-cyclohexanone 
• 344559-87-1 [2-(1-Carbamoylimino-ethyl)-cyclohex-1-enyl]-urea 
• 148192-68-1 N,N'-bis-(2-acetylcyclohexenyl)ethylenediamine 
• 16275-33-5 2-(3-phenylpropanoyl)cyclohexanone 

Relevant articles and documents

Discovery of quinolone derivatives as antimycobacterial agents

Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.

SKLB1039 Compound as well as preparation method and application thereof

The invention belongs to the technical field of preparation of new compounds, and particularly relates SKLB1039 compound as well as a preparation method and application thereof. The 2 -methyl -3 -nitrobenzoic acid is taken as an initial raw material and is brominated. Esterification, reduction, reductive amination and hydrolysis synthesis 5 - bromo -2 - methyl -3 - (N - ethyl, N - (tetrahydropyran -4 - yl)) aminobenzoic acid. The cyclohexanone serving as a raw material is subjected to catalytic hydrogenation reduction of carbonyl α, acetyl cyclohexanone and cyanopyridone to synthesize 4 - aminomethyl -1 - methyl -5, 6, 7, 8 - tetrahydroisoquinoline -3 (2H) - ketone. Coupling the two to an amide is followed by catalytic coupling with an aryl sheet to give SKLB1039 a compound. SKLB1039 Large-scale preparation technology is provided, operation is easy, the post-treatment purification process is simple, the total route yield is improved, raw materials are easy to purchase, the price is low, and the production cost is greatly reduced.

One-pot method for preparation of 2-acetyl cyclohexanone

The invention discloses a one-pot method for preparation of 2-acetyl cyclohexanone. The method comprises the steps of: (1) adding cyclohexanone into tetrahydrofuran, under the condition of icewater bath cooling, adding lithium diisopropylamide dropwise, and then carrying out stirring reaction at room temperature for 1h; (2) under the condition of icewater bath, adding a trichloromethane solution of acetyl chloride into the reaction system of step (1) dropwise, then removing icewater bath, and carrying out stirring reaction at room temperature for 1h; and (3) washing the reaction solution obtained in step (2) twice and performing liquid separation, conducting spin drying of trichloromethane, then carrying out pressure reduced distillation and collecting 118-136DEG C fractions, thus obtaining 2-acetyl cyclohexanone. According to the method, in the whole reaction process, the intermediate products have no need for additional purification treatment and can be directly subjected to next step reaction, and the finally obtained product is refined directly by pressure reduced distillation. The whole process has the advantages of high yield, short reaction time, and low energy consumption. The 2-acetyl cyclohexanone obtained by direct pressure reduced distillation refining has a concentration of more than 96.0wt%, and the yield is more than 94%.