Hexanophenone

Base Information

• Chemical Name: Hexanophenone
• CAS No.: 942-92-7
• Molecular Formula: C12H16O
• Molecular Weight: 176.258
• Hs Code.: 29143900
• European Community (EC) Number: 213-394-6
• NSC Number: 8480
• DSSTox Substance ID: DTXSID4061335
• Nikkaji Number: J30.881A
• Wikidata: Q9696360
• Mol file: 942-92-7.mol

Synonyms:Hexanophenone;942-92-7;1-phenylhexan-1-one;Caprophenone;1-Phenyl-1-hexanone;Amyl phenyl ketone;n-Hexanophenone;Hexaphenone;Pentyl phenyl ketone;1-Hexanone, 1-phenyl-;1-phenyl-hexan-1-one;NSC 8480;EINECS 213-394-6;AI3-01378;1-Benzoylpentane;NSC8480;n-Amylphenyl ketone;MFCD00009512;Hexanophenone, 99%;n-Pentyl phenyl ketone;Hexanophenone, >=99%;SCHEMBL50000;DTXSID4061335;NSC-8480;AKOS000121447;AS-56450;CS-0152336;FT-0633168;H0116;EN300-21120;F21443;Q63409590

Chemical Property of Hexanophenone

Chemical Property:

• Appearance/Colour: clear light yellow liquid after melting
• Vapor Pressure: 0.0094mmHg at 25°C
• Melting Point: 25-26 °C(lit.)
• Refractive Index: n20/D 1.5105(lit.)
• Boiling Point: 265 °C at 760 mmHg
• Flash Point: 105.5 °C
• PSA: 17.07000
• Density: 0.942 g/cm³
• LogP: 3.44960
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 176.120115130
• Heavy Atom Count: 13
• Complexity: 145

Purity/Quality:

99%min ^*data from raw suppliers

Hexanophenone >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C1=CC=CC=C1
• Uses: Caprophenone is an inhibitor of carbonyl reductase activity in pig’s heart cytosol. A useful research chemical.

Technology Process of Hexanophenone

There total 169 articles about Hexanophenone 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: 95.0%

n-hexanoic anhydride (2051-49-2) + phenylboronic acid (98-80-6) → caprophenone (942-92-7) + hexanoic acid (142-62-1)

Guidance literature:

With P(p-CH₃OC₆H₄)3; palladium diacetate; In tetrahydrofuran; water; at 60 ℃; for 16h;

DOI:10.1002/1099-0690(200210)2002:19<3254::AID-EJOC3254>3.0.CO;2-6

Reference yield: 65.0%

cyclopropyl phenyl ketone (3481-02-5) + diethylzinc (557-20-0) → caprophenone (942-92-7) + 1-cyclopropyl-1-phenylethanol (5558-04-3)

Guidance literature:

With bis(acetylacetonate)nickel(II); methyllithium; In tetrahydrofuran; at 0 ℃;

DOI:10.1246/cl.1997.1149

Reference yield: 61.8%

1-phenyl-1-cyclohexane (827-52-1,5379-26-0) → 1-phenylcyclohexanol (1589-60-2) + 1-Phenylcyclohexene (771-98-2) + caprophenone (942-92-7) + 1-phenyl-4-cyclohexanone (4894-75-1) + trans-4-phenylcyclohexanol (5437-46-7,7335-12-8,5769-13-1) + cis-4-phenylcyclohexanol (7335-12-8)

Guidance literature:

With oxygen; 2,2'-azobis(isobutyronitrile); at 120 ℃; for 12h; Product distribution; Thermodynamic data; Mechanism; various temperatures: 130 deg. C, 140 deg. C various conc. of catalyst;

upstream raw materials:

pyridine

bis-(1-phenyl-cyclohexyl)-peroxide

1-bromo-butane

α-methoxystyrene

Downstream raw materials:

2-hydroxy-2-phenyl-heptanoic acid amide

2-phenylheptane-2-ol

(E)-1-phenyl-1,2-hexanedione 2-oxime

2-pentyl-2-phenyl-[1,3]dioxolane

Refernces

• 1、 Zhang, Kezhuo,Huang, Jiaxin,Zhao, Wanxiang. "Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones". supporting information. . Retrieved 2022/02/21.
• 2、 Bhattacharyya, Dipanjan,Sarmah, Bikash Kumar,Nandi, Sekhar,Srivastava, Hemant Kumar,Das, Animesh. "Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols". supporting information. p. 869 - 875. Retrieved 2021/02/06.