Cyclohexylacetone

Base Information

• Chemical Name: Cyclohexylacetone
• CAS No.: 103-78-6
• Molecular Formula: C9H16O
• Molecular Weight: 140.225
• Hs Code.: 2914299000
• European Community (EC) Number: 203-143-9
• NSC Number: 15332
• UNII: V54Y1GAG9I
• DSSTox Substance ID: DTXSID2059279
• Nikkaji Number: J182.168G
• Wikipedia: Cyclohexylacetone
• Wikidata: Q5198719
• Mol file: 103-78-6.mol

Synonyms:Cyclohexylacetone;103-78-6;1-cyclohexylpropan-2-one;2-Propanone, 1-cyclohexyl-;Acetonylcyclohexane;1-Cyclohexylacetone;1-Cyclohexyl-2-propanone;Cyclohexyl-2-propanone;V54Y1GAG9I;EINECS 203-143-9;MFCD00019396;NSC 15332;NSC-15332;AI3-24773;Cyclohexylaceton;cyclohexylacetone-;NSC15332;1-Cyclohexylacetone #;UNII-V54Y1GAG9I;1-cyclohexyl-propan-2-one;methyl cyclohexylmethyl ketone;SCHEMBL363901;1-Cyclohexylacetone, AldrichCPR;DTXSID2059279;2-PROPANONE, CYCLOHEXYL-;AKOS005206704;AS-56904;SY106383;CS-0155063;FT-0624216;C-9205;D84585;EN300-122191;A800804;Q5198719

Chemical Property of Cyclohexylacetone

Chemical Property:

• Appearance/Colour: Liquid
• Vapor Pressure: 0.609mmHg at 25°C
• Melting Point: 116℃
• Refractive Index: 1.4528
• Boiling Point: 188.1 °C at 760 mmHg
• Flash Point: 65.3 °C
• PSA: 17.07000
• Density: 0.889 g/cm³
• LogP: 2.54580
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 140.120115130
• Heavy Atom Count: 10
• Complexity: 112

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Cyclohexylacetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36-52
• Safety Statements: 24/25-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC1CCCCC1
• Uses: 1-Cyclohexyl-2-propanone is a useful reagent for organic synthesis.

Technology Process of Cyclohexylacetone

There total 60 articles about Cyclohexylacetone 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: 60.0%

allylcyclohexane (2114-42-3) → 4-cyclohexyl-butan-2-one (103-78-6) + 3-cyclohexylpropanal (4361-28-8)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; nitromethane; oxygen; tert-butyl alcohol; at 20 ℃; for 6h; under 760.051 Torr; Overall yield = 75 %;

DOI:10.1002/anie.201306756

Reference yield: 60.0%

→ 4-cyclohexyl-butan-2-one (103-78-6) + 3-cyclohexylpropanal (4361-28-8)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; oxygen; In nitromethane; tert-butyl alcohol; at 20 ℃; for 6h; under 760.051 Torr; Overall yield = 75 %;

Reference yield: 55.0%

cyclohexane (110-82-7,25012-93-5) + percarbonate de O,O-tert-butyle et O-isopropyle (65700-06-3) → 4-cyclohexyl-butan-2-one (103-78-6) + cyclohexylcyclohexane (92-51-3) + 2,5-hexanedione (110-13-4) + tert-butyl alcohol (75-65-0)

Guidance literature:

at 130 ℃; for 2.5h; Further byproducts given;

DOI:10.1016/0040-4020(82)80049-5

upstream raw materials:

1-cyclohexenylacetone

Cyclohexyl iodide

sodium ethyl acetylacetate enolate

allylcyclohexane

Downstream raw materials:

2-cyclohexyl-1,1-dimethyl ethanol

1-cyclohexyl-4-dimethylamino-butan-2-one

Cyclohexyl-aceton-semicarbazon

N,N'-bis-(2-cyclohexyl-1-methyl-ethyl)-hydrazine

Refernces

• 1、 Brown, Herbert C.,Imai, Toshiro,Bhat, N. G.. "Vinylic Organoboranes. 7. Stereoselective Synthesis of (E)-(1-Substituted-1-alkenyl)boronic Esters by the Nucleophilic Substitution of (Z)-(1-Bromo-1-alkenyl)boronic Esters with Organolithium or Grignard Reagents. Isolation and Oxidation to Ketones.". . p. 5277 - 5282. Retrieved 1986.
• 2、 Hajek et al.. "-". . p. 3193. Retrieved 1974.
• 3、 Tosaki, Shin-Ya,Hara, Keiichi,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu. "Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution". . p. 11776 - 11777. Retrieved 2006.
• 4、 Komori, Saki,Yamaguchi, Yoshiko,Murakami, Yuka,Kataoka, Yasutaka,Ura, Yasuyuki. "Palladium/Copper-catalyzed Oxidation of Aliphatic Terminal Alkenes to Aldehydes Assisted by p-Benzoquinone". . p. 3946 - 3955. Retrieved 2020.
• 5、 Bailey,Daly. "-". . p. 1189,1192. Retrieved 1957.
• 6、 Hara, Keiichi,Tosaki, Shin-ya,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu. "Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution". . p. 5030 - 5036. Retrieved 2009.
• 7、 -. "Preparation method of cyclohexyl acetone". Paragraph 0009; 0041-0062. . Retrieved 2021/05/29.