2-Phenylcyclohexanone

Base Information

• Chemical Name: 2-Phenylcyclohexanone
• CAS No.: 1444-65-1
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Hs Code.: 29143900
• European Community (EC) Number: 215-888-7
• NSC Number: 22252
• DSSTox Substance ID: DTXSID501314883
• Nikkaji Number: J1.766C
• Wikidata: Q106902664
• Mol file: 1444-65-1.mol

Synonyms:2-Phenylcyclohexanone;1444-65-1;2-phenylcyclohexan-1-one;Cyclohexanone, 2-phenyl-;Cyclohexanone, phenyl-;2-phenyl cyclohexanone;EINECS 215-888-7;MFCD00001629;NSC 22252;AI3-07036;2-Phenyl-cyclohexanone;phenyl cyclohexanone;NSC22252;2- phenylcyclohexanone;Cyclohexanone,2-phenyl-;rac-2-phenylcyclohexanone;2-phenyl-cyclohexan-1-one;2-Phenylcyclohexanone, 98%;SCHEMBL190786;(+/-)-2-phenylcyclohexanone;DRLVMOAWNVOSPE-UHFFFAOYSA-;DTXSID501314883;CS-B0294;NSC-22252;AKOS000121318;AKOS016038082;AC-18814;DS-12149;SY048753;FT-0633543;P1311;EN300-21657;A808217;J-007953;Z104507604;2,2-BIS(4-CARBOXY-3-NITROPHENYL)HEXAFLUOROPROPANE98

Chemical Property of 2-Phenylcyclohexanone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00167mmHg at 25°C
• Melting Point: 56-59 °C(lit.)
• Refractive Index: 1.537
• Boiling Point: 294 °C at 760 mmHg
• Flash Point: 123.7 °C
• PSA: 17.07000
• Density: 1.042 g/cm³
• LogP: 2.91330
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 174.104465066
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

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

2-Phenylcyclohexanone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: C1CCC(=O)C(C1)C2=CC=CC=C2
• Uses: 2-Phenylcyclohexanone is a substrate for steroid monooxygenase (STMO) from Rhodococcus rhodochrous DSM 43269.

Technology Process of 2-Phenylcyclohexanone

There total 229 articles about 2-Phenylcyclohexanone 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: 99.0%

trans-2-Phenylcyclohexanol (2362-61-0) → (RS)-2-phenylcyclohexanone (1444-65-1)

Guidance literature:

With peracetic acid; 2,4-dimethyl-2,4-pentanediol cyclic Cr(VI) ester; In tetrachloromethane; dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)98245-5

Reference yield: 88.0%

2-phenylcyclohexanol (1444-64-0) → (RS)-2-phenylcyclohexanone (1444-65-1)

Guidance literature:

With pivaloyl chloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 1h;

DOI:10.1080/00397910701820343

Reference yield: 86.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + chlorobenzene (108-90-7) → (RS)-2-phenylcyclohexanone (1444-65-1)

Guidance literature:

With sodium t-butanolate; [(IPr)Pd(acac)Cl]; In toluene; at 60 ℃; for 2h;

DOI:10.1016/j.tet.2005.06.081

upstream raw materials:

phenyldiazomethane

cyclopentanone

1-phenylcyclohexene oxide

(E)-3-Ureido-but-2-enoic acid ethyl ester

Downstream raw materials:

2-<(dimethylamino)methyl>-6-phenylcyclohexanone

2-allyl-2-phenylcyclohexan-1-one

3-(2-oxo-1-phenyl-cyclohexyl)-propionic acid ethyl ester

(+/-)-1-hydroxy-2t-phenyl-cyclohexane-carbonitrile-(1r)

Refernces

• 1、 House,H.O. et al.. "-". . p. 8471 - 8475. Retrieved 1972.
• 2、 Das, Anjan,Ayad, Suliman,Hanson, Kenneth. "Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes". . p. 5416 - 5419. Retrieved 2016.
• 3、 Oshita, Masayuki,Okazaki, Takao,Ohe, Kouichi,Chatani, Naoto. "GaCl3-catalyzed skeletal rearrangement of α,α, α-trisubstituted aldehydes". . p. 331 - 334. Retrieved 2005.
• 4、 Nakamura, Yutaka,Takeuchi, Seiji,Ohgo, Yoshiaki,Yamaoka, Makoto,Yoshida, Akihiro,Mikami, Koichi. "SmI2-mediated reductive enolization of α-hetero-substituted ketones and enantioselective protonation". . p. 2709 - 2712. Retrieved 1997.
• 5、 Yanagisawa, Akira,Inanami, Hiroshi,Yamamoto, Hisashi. "Chiral aminoborane as a chiral proton source for asymmetric protonation of lithium enolates derived from 2-arylcycloalkanones". . p. 1573 - 1574. Retrieved 1998.
• 6、 Zhao, Kejun,Wang, Yongfeng,Zhao, Linxiang,Ji, Zhizhong,Li, Dan,Tisdale, Michael J.,Schwalbe, Carl H.. "Synthesis and cytotoxicity of a novel 1-alkylaminomethyl-2,4-diaryl- butadiene-1,3 fragment integrated within cyclohex(pent)enes". . p. 373 - 379. Retrieved 2004.
• 7、 Fort, Yves,Christophe, Stephanie,Caubere, Paul. "Template Aggregative Activation: Metal Salt-reinforced Complex Bases in Arynic Synthesis". . p. 334 - 335. Retrieved 1997.
• 8、 Ishihara, Kazuaki,Nakamura, Hiroko,Nakamura, Shingo,Yamamoto, Hisashi. "Highly Regio- and Stereoselective Isomerization of Sylyl Enol Ethers Catalyzed by LBA. A Remarkable Enantiomer Discrimination of Chiral LBA". . p. 6444 - 6445. Retrieved 1998.
• 9、 Nakashima, Daisuke,Yamamoto, Hisashi. "Titanium tetrachloride and chiral aliphatic alcohol as a new Lewis acid assisted chiral Br?nsted acid for the enantioselective protonation of silyl enol ether". . p. 150 - 152. Retrieved 2006.
• 10、 Gao, Bo,Xu, Zeyu,Fan, Luan,Xu, Xiaodong,Bai, Jianwei,Shen, Xiande. "Synthesis and chiral recognition ability of a novel fullerene-functionalized cellulose derivative". . p. 1479 - 1481. Retrieved 2015.