1660-04-4

Basic information

• Product Name: 1-Adamantyl methyl ketone
• Synonyms: METHYL 1-ADAMANTYL KETONE;LABOTEST-BB LT00007823;IFLAB-BB F1928-0002;1-(1-ADAMANTYL)ETHANONE;1-(1-ADAMANTYL)ETHAN-1-ONE;1-ADAMANTYL METHYL KETONE;1-Acetyl-tricyclo[3.3.1.1(3,7)]decane;1-ACETYLADAMANTANE
• CAS NO: 1660-04-4
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.27
• EINECS: 216-761-9
• Product Categories: Adamantane derivatives;Adamantanes;C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 1660-04-4.mol

Chemical Properties

• Melting Point: 53-55 °C(lit.)
• Boiling Point: 250.52°C (rough estimate)
• Flash Point: 227 °F
• Appearance: White/Crystalline Powder
• Density: 0.9172 (rough estimate)
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.5050 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in methanol- very faint turbidity. Insoluble in water.
• CAS DataBase Reference: 1-Adamantyl methyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Adamantyl methyl ketone(1660-04-4)
• EPA Substance Registry System: 1-Adamantyl methyl ketone(1660-04-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 1660-04-4(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1-Adamantyl methyl ketone is used as an important intermediate for various organic synthesis processes due to its unique structural properties and reactivity.
2. Used in Pharmaceutical Industry:
1-Adamantyl methyl ketone is utilized as a key raw material in the development of pharmaceuticals, contributing to the synthesis of various medicinal compounds.
3. Used in Agrochemicals:
In the agrochemical industry, 1-Adamantyl methyl ketone serves as a vital intermediate for the production of different agrochemical products, enhancing their effectiveness and performance.
4. Used in Dye Industry:
1-Adamantyl methyl ketone is employed as a significant raw material in the dye industry, playing a crucial role in the synthesis of various dyes and pigments.

InChI:InChI=1/C12H18O/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h9-11H,2-7H2,1H3

Upstream product

• 40430-66-8 1-ethynyladamantane 
• 768-90-1 1-Adamantyl bromide 
• 74-86-2 acetylene 
• 108-05-4 vinyl acetate 
• 281-23-2 adamantane 
• 876-53-9 1,3-dibromoadamantane 
• 5122-82-7 1-adamantyl bromomethyl ketone 
• 828-51-3 1-Adamantanecarboxylic acid 
• 917-54-4 methyllithium 
• 775-64-4 2-(1-adamantyl)-2-propanol 
• 917-64-6 methyl magnesium iodide 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 506-82-1 dimethylcadmium 
• 133189-53-4 3,4-Dihydroxy-4-methyltricyclo<4.3.1.1^3,8>undecane 

Downstream Products

• 119778-65-3 2-(1-Adamantyl)-4-carboxyquinoline 
• 76325-80-9 3-Hydroxy-3-<(1-adamantyl)carbonylmethyl>oxindole 
• 135120-66-0 1-(1-Adamantyl)-3-(4-fluorophenyl)-2-propen-1-one 
• 91410-69-4 1-adamantylethanol 
• 13392-28-4 rimantadine 
• 88313-73-9 (1-adamantan-1-ylethyl)butyl amine 
• 99875-21-5 2-(1-Adamantyl)-2,4-bis<2-hydroxyphenylmethylenamino>-2,3-dihydro-4H-1-benzopyran 
• 20440-81-7 1-tert-butyladamantane 
• 79606-54-5 N-<1-(1-adamantyl)ethylidene>cyclohexylamine 
• 88313-74-0 (1-adamantan-1-yl-ethyl)-benzyl-amine 
• 602-98-2 3-benzoyl-6-phenylpyran-2,4-dione 
• 84421-03-4 2-Methyl-2-(1-adamantyl)-6-phenyl-1,3-dioxen-4-one 
• 88313-72-8 N-(n-propyl)-α-methyl-1-adamantylmethylamine 
• 116755-49-8 1-(1-adamantyl)-1-(4-hydroxyphenyl)ethene 

Related news

Structural effects on the thermochemical properties of carbonyl compounds II. enthalpies of combustion, vapour pressures and enthalpies of sublimation, and standard enthalpies of formation in the gaseous phase, of 1-Adamantyl methyl ketone (cas 1660-04-4) and of 1,1′-diadamantyl ketone09/07/2019

The energies of combustion of 1-adamantyl methyl ketone, and 1,1'-diadamantyl ketone have been determined using a static bomb calorimeter. The vapour pressures have been measured over a temperature range of about 17K by the Knudsen-effusion technique. From the experimental results the follo...detailed

Relevant articles and documents

Preparation of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid: A key intermediate for saxagliptin

An optimized synthetic approach to prepare 2-(3-hydroxy-1-adamantyl)-2- oxoacetic acid has been reported in a good yield under mild experimental conditions. It was synthesized from 1-adamantanecarboxylic acid via successful reaction with thionyl chloride and sodium diethyl malonate to give dimethyl (1-adamantylcarbonyl) malonate, which was subjected to hydrolysis and decarboxylation by a mixture of acetic acid with water and sulfuric acid and then oxidation by potassium permanganate. The synthesized adamantane derivative was utilized to saxagliptin.

Synthesis of 1-acetyladamantane by reaction of 1-bromoadamantane with vinyl acetate and ethylidene diacetate catalyzed by Mn2(CO)10

A procedure has been developed for the synthesis of 1-acetyladamantane in 95% yield by reaction of 1-bromoadamantane with vinyl acetate or ethylidene diacetate in the presence of manganese complexes.

The Mn(acac)3-RCN-CCl4 system as a new efficient reagent for the oxidation of secondary alcohols into ketones

The Mn(acac)3-RCN-CCl4 system was found to be efficient for the oxidation of secondary alcohols into the corresponding ketones in 80-93% yields. The oxidation proceeds through the formation of alkyl hypochlorites, which are generated from CCl4 and the alcohols in the presence of the Mn(acac)3-RCN catalytic system (R = Me, Et, and Ph).

Selective Nitroxylation of Adamantane Derivatives in the System Nitric Acid–Acetic Anhydride

Abstract: A number of new nitroxyadamantanes have been synthesized by nitroxylation of the corresponding substrates with nitric acid in acetic anhydride. High electrophilicity and reduced acidity of the system HNO3–Ac2O increases the stability of nitrates and significantly decreases the probability of formation of alcohols. In some cases, nitrolysis and oxidation of functional groups in the substrate are observed.

Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes

An efficient visible light photoredox catalyzed aerobic deprotection of 1,3-oxathiolanes using organic dye Eosin Y as a photocatalyst is disclosed. The deprotection procedure features the use of a metal-free catalyst, mild conditions, a broad range of substrate scope, and good functional group tolerance. 35 examples were tested under the standard conditions and most of them afforded the deprotected products in modest to high yields.

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source

Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.

Preparation method of 1-adamantyl methy ketone

The invention belongs to the field of preparation of chemical intermediates, and particularly relates to a preparation method of 1-adamantyl methy ketone. The preparation method comprises the following steps of step 1, enabling adamantane and liquid bromine to react, so as to obtain 1-bromoadamantane; step 2, using concentrated sulfuric acid as a catalyst, adding the 1-bromoadamantane and n-hexane, and dripping formic acid, so as to obtain 1-adamantanecarboxylic acid; step 3, enabling the 1-adamantanecarboxylic acid and thionyl chloride to react, heating and refluxing, extracting by benzene, and directly applying the extracting liquid for the reaction in next step; step 4, dripping a mixed solution of benzene, diethyl malonate and anhydrous ethyl alcohol into a mixed solution of magnesiumpowder, iodine, anhydrous ethyl alcohol and benzene, dripping a benzene solution of 1-adamantanecarbonyl chloride, extracting by benzene, drying and distilling, so as to obtain 2- adamantanecarbonyl diethyl malonate; step 5, adding glacial acetic acid, water and concentrated sulfuric acid into the residue. The preparation method has the advantage that the yield rate is high.

Preparation method of rimantadine hydrochloride preparation

The invention discloses a preparation method of a rimantadine hydrochloride preparation. The preparation method comprises the following steps: preparation of 1-bromoadamantane, preparation of amantadecanoic acid, preparation of adamantanecarbonyl chloride, preparation of adamantyl methy ketone, preparation of 1-amantadine methyl ketone oxime, preparation of rimantadine hydrochloride, and preparation of the rimantadine hydrochloride preparation. The preparation of adamantyl methy ketone comprises the following steps: adding (CH3)3Sb and nickelous formate into a flask; dropwise adding an acetonitrile solution of adamantanecarbonyl chloride, wherein adamantanecarbonyl chloride reacts with (CH3)3Sb to generate adamantyl methy ketone; after reaction, pouring a reaction liquid into ice water; and filtering and drying the mixture to obtain a light yellow precipitate, thereby obtaining the adamantyl methy ketone. The preparation method has the beneficial effects that the preparation method ofrimantadine hydrochloride preparation is good in environmental protection, mild in condition of a synthetic method, simple and feasible in process and high in product yield.

Synthesizing method of rimantadine hydrochloride

The invention discloses a synthesizing method of rimantadine hydrochloride. The synthesizing method comprises the following steps of preparing of 1-bromoadamantane, preparing of adamantane carboxylicacid, preparing of adamantanecarbonyl chloride, preparing of adamantyl methyl ketone, preparing of 1-amantadine methyl ketone oxime, preparing of rimantadine hydrochloride, and preparing of a rimantadine hydrochloride preparation; in the preparing process of adamantyl methyl ketone: adding trimethylaluminum and cerium formate into a flask, then dripping a benzene solution of adamantanecarbonyl chloride, and enabling the adamantanecarbonyl chloride and the trimethylaluminum to react and generate adamantyl methyl ketone; after reaction is finished, pouring a reaction solution into ice water, filtering and drying, so as to obtain a light yellow precipitate, namely the adamantyl methyl ketone. The synthesizing method has the beneficial effects that the conditions are mild, and the technology is simple and feasible; the usage amount of catalyst is small, the environment-friendly effect is realized, and the yield of product is high.

A kind of anti-influenza virus preparation

The present invention discloses an anti-influenza virus preparation, including 1 - bromo adamantane preparation, adamantane formic acid preparation, adamantane chloride preparation, adamantane methyl preparation, 1 - adamantane methyl oxime preparation, hydrochloric acid rimantadine preparation, anti-influenza virus preparation, wherein the adamantane methyl preparation steps are as follows: in the flask to join the three trimethylaluminum, formic acid cerium, then dropwise adamantane formyl chloride [...], the adamantane chloride with three methyl aluminum reaction generating adamantane methyl ketone, after the reaction is completed in the reaction liquid into ice water, then filtering, drying, the resulting pale yellow precipitate adamantane methyl ketone. The beneficial effects: preparation method of this invention mild condition, the process is simple and feasible, high product yield, the system anti- influenza virus preparation can be effective prevention and treatment of type a/b influenza virus infection, also can effectively alleviate the symptoms of the common cold.