1-Adamantyl methyl ketone

Base Information

• Chemical Name: 1-Adamantyl methyl ketone
• CAS No.: 1660-04-4
• Molecular Formula: C12H18O
• Molecular Weight: 178.274
• Hs Code.: 29142990
• European Community (EC) Number: 216-761-9
• DSSTox Substance ID: DTXSID60168059
• Nikkaji Number: J80.276J
• Mol file: 1660-04-4.mol

Synonyms:1-Adamantyl methyl ketone;1660-04-4;1-Acetyladamantane;1-(1-Adamantyl)ethanone;1-adamantylmethylketone;1-(adamantan-1-yl)ethan-1-one;Methyl 1-adamantyl ketone;MFCD00074739;Adamantyl methyl ketone;1-Adamantan-1-yl-ethanone;Ethanone, 1-tricyclo[3.3.1.13,7]decyl-;1-((3r,5r,7r)-adamantan-1-yl)ethan-1-one;Methyl tricyclo(3.3.1.13,7)dec-1-yl ketone;EINECS 216-761-9;Ethanone, 1-tricyclo[3.3.1.1(3,7)-]dec-1-yl-;acetyladamantane;1-(adamantan-1-yl)ethanone;Ethanone, 1-tricyclo(3.3.1.13,7)dec-1-yl-;Ethanone, 1-tricyclo[3.3.1.13,7]dec-1-yl-;Methyl tricyclo[3.3.1.13,7]dec-1-yl ketone;Ethanone, 1-tricyclo(3.3.1.1(3,7)-)dec-1-yl-;Acetyldamantane;1-(1-adamantyl)ethan-1-one;1-Acetyl-adamantane;Methyl adamantyl ketone;Methyl adamantyl-1 ketone;Ketone, 1-adamantyl methyl;adamantan-1-yl-ethan-1-one;adamantan-1-yl methyl ketone;SCHEMBL159994;1-(1-adamantyl)-1-ethanone;SCHEMBL19757635;DACIGVIOAFXPHW-UHFFFAOYSA-;DTXSID60168059;1-Adamantyl methyl ketone, 99%;STK387539;AKOS000121013;AKOS000423113;AKOS005146501;AM84568;AS-9177;Tricyclo[3.3.1.13.7]decan-1-acetyl;AC-11126;SY023641;1-Acetyl-tricyclo[3.3.1.1(3,7)]decane;CS-0063144;FT-0633741;EN300-16795;VU0494587-1;1-(tricyclo[3.3.1.13,7]dec-1-yl)ethanone;Ethanone,1-tricyclo[3.3.1.13,7]dec-1-yl-;1-(tricyclo[3.3.1.1~3,7~]dec-1-yl)ethanone;Ethanone, 1-tricyclo[3.3.1.1<3,7>dec-1-yl-;Ethanone, 1-tricyclo[3.3.1.13#,7]dec-1-yl-;W-107929;F1928-0002

Chemical Property of 1-Adamantyl methyl ketone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.011mmHg at 25°C
• Melting Point: 53-55 °C(lit.)
• Refractive Index: 1.532
• Boiling Point: 262.3 °C at 760 mmHg
• Flash Point: 108.3 °C
• PSA: 17.07000
• Density: 1.077 g/cm³
• LogP: 2.79180
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol- very faint turbidity. Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 178.135765193
• Heavy Atom Count: 13
• Complexity: 213

Purity/Quality:

99% ^*data from raw suppliers

1-Acetyladamantane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C12CC3CC(C1)CC(C3)C2
• Uses: 1-Adamantyl methyl ketone, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of 1-Adamantyl methyl ketone

There total 73 articles about 1-Adamantyl methyl ketone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

acetonitrile (75-05-8,26809-02-9) + trans-N,N'-bis(1-adamantyl)diazene (24325-56-2) → 1,1'-Biadamantane (3732-31-8) + adamantane (281-23-2) + N-(1-adamantyl)acetamide (880-52-4) + 1-acetyladamantane (1660-04-4)

Guidance literature:

With thianthrenium perchlorate; Further byproducts given; Ambient temperature;

DOI:10.1021/ja00294a066

Reference yield: 90.0%

acetonitrile (75-05-8,26809-02-9) + trans-N,N'-bis(1-adamantyl)diazene (24325-56-2) → 1,1'-Biadamantane (3732-31-8) + 1-adamanthanol (768-95-6) + N-(1-adamantyl)acetamide (880-52-4) + 1-acetyladamantane (1660-04-4)

Guidance literature:

With thianthrenium perchlorate; Further byproducts given; Ambient temperature;

DOI:10.1021/ja00294a066

Reference yield: 90.0%

trimethylaluminum (75-24-1) + 1-Adamantanecarbonyl chloride (2094-72-6) → 1-acetyladamantane (1660-04-4)

Guidance literature:

With cesium formate; In benzene; Inert atmosphere; Green chemistry;

upstream raw materials:

1-ethynyladamantane

1-Adamantyl bromide

acetylene

vinyl acetate

Downstream raw materials:

2-(1-Adamantyl)-4-carboxyquinoline

3-Hydroxy-3-<(1-adamantyl)carbonylmethyl>oxindole

1-(1-Adamantyl)-3-(4-fluorophenyl)-2-propen-1-one

1-adamantylethanol

Refernces

• 1、 Tabushi,I. et al.. "-". . p. 2370 - 2374. Retrieved 1978.
• 2、 Bae, Dong Hak,Engel, Paul S.,Hoque, A. K. M. Mansurul,Keys, Dalen E.,Lee, Wang-Keun,et al.. "Oxidative Decomposition of 1,1'-Azoadamantane by Thianthrene Cation Radical. Carbocationic Chemistry from a Free Radical Source". . p. 2561 - 2562. Retrieved 1985.
• 3、 Tabushi et al.. "-". . p. 2329. Retrieved 1973.
• 4、 Bott. "-". . p. 1349. Retrieved 1969.
• 5、 Ivleva, E. A.,Klimochkin, Yu. N.,Moiseev, I. K.. "Selective Nitroxylation of Adamantane Derivatives in the System Nitric Acid–Acetic Anhydride". . p. 1532 - 1539. Retrieved 2020.
• 6、 Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.. "Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source". supporting information. p. 7683 - 7689. Retrieved 2020/04/22.
• 7、 -. "Preparation method of rimantadine hydrochloride preparation". . . Retrieved 2019/02/04.