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
• Article Data: 60

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

Description

1-Adamantyl methyl ketone is a sterically bulky ketone substrate that is known for its excellent optical purity when reduced to the corresponding alcohol. It is characterized by its white crystalline powder appearance.

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

• 57680-77-0 adamantylmagnesium bromide 
• 141-78-6 ethyl acetate 
• 75-05-8 acetonitrile 
• 24325-56-2 trans-N,N'-bis(1-adamantyl)diazene 
• 6600-42-6 1-vinyladamantane 
• 768-90-1 1-Adamantyl bromide 
• 108-24-7 acetic anhydride 
• 75-16-1 methylmagnesium bromide 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 1041846-07-4 C₁₄H₂₁NO 
• 1707-40-0 1-((3r,5r,7r)-adamantan-1-yl)ethan-1-one oxime 
• 74-86-2 acetylene 
• 917-54-4 methyllithium 
• 2094-74-8 1-Adamantanecarbaldehyde 

Downstream Products

• 13392-28-4 rimantadine 
• 119159-11-4 3-(1-adamantyl)-1-phenyl-1-propen-3-one 
• 88313-74-0 (1-adamantan-1-yl-ethyl)-benzyl-amine 
• 709031-28-7 3-hydroxy-α-oxotricyclo [3.3.1.1^3,7]decane-1-acetic acid 
• 920693-25-0 2-(1-adamantyl)-4-(4-methylphenyl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridine 
• 920672-17-9 2-(1-adamantyl)-4-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine 
• 82094-52-8 1-(1-adamantyl)butane-1,3-dione 
• 758709-48-7 1-(1-adamantyl)-4,4,4-trifluoro-1,3-butanedione 

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

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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.

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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).

Vinylation and acylation of adamantane by vinyl acetate through the action of rhodium complexes

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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.

Catalyst-Free Photodriven Reduction of α-Haloketones with Hantzsch Ester

Catalyst-free dehalogenation of α-haloketones under visible light irradiation is studied. The reactions were carried out in common organic solvent. The outcomes of dechlorination are excellent in yields up to 92%, and it is also applicable to bromides, which give even higher yields. The reaction is tolerable to a broad spectrum of substrates, especially to aromatic ketones, including various aryl and hetaryl groups. There are two examples of aliphatic ketones presented in the paper, although their reactivities are not as high as that of the aromatic ketones.