60308-50-1

Basic information

• Product Name: 2-HYDROXYCYCLOHEXANONE DIMER
• Synonyms: 2-HYDROXYCYCLOHEXANONE DIMER;ADIPOIN DIMER;1,2,3,4,5a,6,7,8,9,10a-decahydrodibenzo-p-dioxin-4a,9a-diol
• CAS NO: 60308-50-1
• Molecular Formula: C₁₂H₂₀O₄
• Molecular Weight: 228.28
• EINECS: 208-570-4
• Mol File: 60308-50-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 100-107 °C(lit.)
• Boiling Point: 83-86 °C13 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: /
• Density: 1.297±0.06 g/cm3(Predicted)
• PKA: 11.94±0.40(Predicted)
• CAS DataBase Reference: 2-HYDROXYCYCLOHEXANONE DIMER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYCYCLOHEXANONE DIMER(60308-50-1)
• EPA Substance Registry System: 2-HYDROXYCYCLOHEXANONE DIMER(60308-50-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1325 4.1/PG 3
• WGK Germany: 3
• F: 9-21
• Hazardous Substances Data: 60308-50-1(Hazardous Substances Data)

Upstream product

• 6838-67-1 1,2-bis(trimethylsilyloxy)cyclohex-1-ene 
• 1792-81-0 cis-1,2-cyclohexane 
• 141-28-6 diethyl adipate 
• 533-60-8 cyclohexanone-2-ol 
• 822-87-7 2-Chlorocyclohexanone 
• 931-17-9 1,2-Cyclohexanediol 

Downstream Products

• 36713-55-0 (±)-2-benzyloxycyclohexanone 
• 1207516-50-4 2-(4-bromo-1H-indol-3-yl)cyclohexanone 
• 1207516-51-5 2-(5-fluoro-1H-indol-3-yl)cyclohexanone 
• 1207516-49-1 2-(4-fluoro-1H-indol-3-yl)cyclohexanone 
• 68221-96-5 2-(1H-indol-3-yl)cyclohexan-1-one 
• 1027048-52-7 [2-Ethoxy-cyclohex-(E)-ylidene]-((R)-1-phenyl-ethyl)-amine 
• 745776-46-9 ((1S,2R)-2-Methoxy-cyclohexyl)-((S)-1-phenyl-ethyl)-amine 
• 301651-22-9 2-(1-ethoxy-2-iodo-ethoxy)-cyclohexanone O-methyl-oxime 
• 301651-23-0 N-(2-ethoxy-hexahydro-benzofuran-3a-yl)-O-methyl-hydroxylamine 

Relevant articles and documents

Chemoselective Pd-catalyzed oxidation of polyols: Synthetic scope and mechanistic studies

The regio- and chemoselective oxidation of unprotected vicinal polyols with [(neocuproine)Pd(OAc)]2(OTf)2 (1) (neocuproine = 2,9-dimethyl-1,10-phenanthroline) occurs readily under mild reaction conditions to generate α-hydroxy ketones. The oxidation of vicinal diols is both faster and more selective than the oxidation of primary and secondary alcohols; vicinal 1,2-diols are oxidized selectively to hydroxy ketones, whereas primary alcohols are oxidized in preference to secondary alcohols. Oxidative lactonization of 1,5-diols yields cyclic lactones. Catalyst loadings as low as 0.12 mol % in oxidation reactions on a 10 g scale can be used. The exquisite selectivity of this catalyst system is evident in the chemoselective and stereospecific oxidation of the polyol (S,S)-1,2,3,4-tetrahydroxybutane [(S,S)-threitol] to (S)-erythrulose. Mechanistic, kinetic, and theoretical studies revealed that the rate laws for the oxidation of primary and secondary alcohols differ from those of diols. Density functional theory calculations support the conclusion that β-hydride elimination to give hydroxy ketones is product-determining for the oxidation of vicinal diols, whereas for primary and secondary alcohols, pre-equilibria favoring primary alkoxides are product-determining. In situ desorption electrospray ionization mass spectrometry (DESI-MS) revealed several key intermediates in the proposed catalytic cycle.

Diastereoselective α-iminoamine rearrangement: Asymmetric synthesis of (R)-(-)- and (S)-(+)-2-benzyl-2-hydroxy-cyclohexanone

A convenient asymmetric synthesis of both (R)-(-)- and (S)-(+)-2- benzyl-2-hydroxycyclohexanones starting from racemic 2- benzyloxycyclohexanone and the chiral auxiliary 1-phenylethylamine is reported. The route involves a [1,3]-sigmatropic shift and a ne

N-Hydroxyphthalimide as an Effective Mediator for the Oxidation of Alcohols by Electrolysis

N-Hydroxyphthalimide is shown to be an effective electron carrier in the electrochemical oxidation of alcohols to the corresponding carbonyl compounds.