3155-01-9

Basic information

• Product Name: 3-hydroxy-3-phenyl-butan-2-one
• Synonyms: 3-hydroxy-3-phenyl-butan-2-one
• CAS NO: 3155-01-9
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• Mol File: 3155-01-9.mol

Chemical Properties

• Boiling Point: 267.1°Cat760mmHg
• Flash Point: 111.2°C
• Appearance: /
• Density: 1.089g/cm³
• Vapor Pressure: 0.00414mmHg at 25°C
• Refractive Index: 1.525
• PKA: 12.40±0.29(Predicted)
• CAS DataBase Reference: 3-hydroxy-3-phenyl-butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-3-phenyl-butan-2-one(3155-01-9)
• EPA Substance Registry System: 3-hydroxy-3-phenyl-butan-2-one(3155-01-9)

Safety Data

• Hazardous Substances Data: 3155-01-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12O2/c1-8(11)10(2,12)9-6-4-3-5-7-9/h3-7,12H,1-2H3

Upstream product

• 127-66-2 2-Phenyl-3-butyn-2-ol 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 2674-04-6 diphenyl cadmium 
• 431-03-8 dimethylglyoxal 
• 71-43-2 benzene 
• 6007-26-7 2-methyl-1,3-dithian 
• 98-86-2 acetophenone 
• 515-30-0 2-phenyllactic acid 
• 917-54-4 methyllithium 
• 56955-40-9 acetic acid 1-methyl-2-oxo-1-phenyl-propyl ester 
• 61031-55-8 3-cyclohexyl-4-hydroxy-5,5-dimethyl-4-phenyl-oxazolidin-2-one 
• 75-36-5 acetyl chloride 
• 82571-41-3 tert-butyl hydrazone of acetaldehyde 
• 61031-52-5 4-hydroxy-3,5,5-trimethyl-4-phenyl-oxazolidin-2-one 

Downstream Products

• 101255-75-8 2-hydroxy-2-phenyl-5-piperidino-pentan-3-one; hydrochloride 
• 100706-38-5 1-acetoxy-3-hydroxy-3-phenyl-butan-2-one semicarbazone 
• 100054-40-8 optically inactive 3-methylamino-2-phenyl-butan-2-ol 
• 64969-62-6 methyl-(1-methyl-2-phenyl-propyl)-amine 
• 13562-17-9 5-(1-Hydroxy-cyclopentyl)-3-methyl-2-phenyl-pentin-⁽⁴⁾-diol-(2,3) 
• 4564-83-4 Acetic acid (1S,2S)-2-hydroxy-1-methyl-2-phenyl-propyl ester 
• 13562-18-0 2,3-Dihydroxy-5-(1-hydroxy-cyclohexyl)-3-methyl-2-phenyl-pentin-⁽⁴⁾ 
• 7476-35-9 3-[(E)-Butylimino]-2-phenyl-butan-2-ol 
• 13799-51-4 3,6-Dimethyl-2-phenyl-2,3,6-trihydroxy-heptin-⁽⁴⁾ 
• 13562-16-8 3,6-Dimethyl-2,3,6-trihydroxy-2-phenyl-octin-⁽⁴⁾ 
• 72420-48-5 6-methyl-6-phenyltetrahydropyran-2,3,5-trione 
• 109916-58-7 2-Methyl-2-phenyl-furan-3-one 
• 7473-98-5 2-hydroxy-2-methylpropiophenone 
• 72429-82-4 methyl 4,5-dihydro-5-methyl-4-oxo-5-phenyl-2-furancarboxylate 

Relevant articles and documents

Novel routes to N-amino-1H-pyrrolo[2,3-b]pyridines from α-hydroxyarylalkyl ketones and hydrazines

Treatment of 3-hydroxy-3-(3-pyridyl)butan-2-one hydrazone with polyphosphoric acid gave 1-amino-2,3-dimethyl-1H-pyrrolo[2,3-b]pyridine. An analogous reaction with 2,4-dinitrophenylhydrazone of the same ketone yielded 1-(2,4-dinitrophenyl)-3-methyl-4-(3-pyridyl)pyrazole.

Improved method for samarium diiodide induced reductive coupling reactions of acid halides

Acid halides are known to be reductively coupled with aldehydes and ketones in the presence of samarium diiodide to generate α-hydroxy ketones. Low yields coupled product are obtained due to the competitive process of tetrahydrofuran attack on the acid chloride. This competitive reaction can be avoided and yields improved by preparation of samarium diiodide in acetonitrile.

ELECTRO-OPTIC POLYMER

The present invention provides an electro-optic polymer (EO polymer) comprising an electro-optic molecule (EO molecule) and a base polymer. The EO polymer of the present invention has good performance over the entire optical communication wavelength range

An efficient and recyclable AgNO3/ionic liquid system catalyzed atmospheric CO2 utilization: Simultaneous synthesis of 2-oxazolidinones and α-hydroxyl ketones

Oxazolidinones and α-hydroxyl ketones are two series of fine chemicals that have been generally utilized in biological, pharmaceutical, and synthetic chemistry. Herein, a AgNO3/ionic liquid (IL) catalytic system was developed for the simultaneous synthesis of these compounds through the atom-economical three-component reactions of propargyl alcohols, 2-aminoethanols, and CO2. Notably, this system behaved excellent catalytic activity with the lowermost metal loading of 0.25 mol%. Meanwhile, it is the first reported metal-catalyzed system that could efficiently work under atmospheric CO2 pressure and be recycled at least five times. Evaluation of the green metrics proved the AgNO3/IL-catalyzed processes to be relatively more sustainable and greener than the other Ag-catalyzed examples. Further mechanistic investigations revealed the derivative active species of N-heterocyclic carbene (NHC) silver complexes and CO2 adducts generated during the process. Subsequently, their reactivity in this reaction was assessed for the first time, which was finally identified as beneficial for the catalytic activity.

A green and recyclable CuSO4·5H2O/ionic liquid catalytic system for the CO2-promoted hydration of propargyl alcohols: an efficient assembly of α-hydroxy ketones

α-Hydroxy ketones are important building blocks in biological, pharmaceutical and synthetic chemistry. In this work, diverse α-hydroxy ketones were efficiently constructed through the CO2-promoted hydration process of propargyl alcohols, which was catalyzed by a system consisted of economical CuSO4·5H2O and a green 1-butyl-3-methylimidazolium acetate ionic liquid. Particularly, this catalytic system exhibited excellent activity under atmospheric CO2 or even mimetic flue gas (20 vol% of CO2). Moreover, this system employed the lowest metal loading ever reported (0.004–0.25 mol%) meanwhile reached the highest turnover number (11700) for the target hydration reaction. Additionally, this is the first reported Cu catalytic system with reliable recyclability, which could be easily reused at least 6 times with yields higher than 85%.

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

D-π-A chromophores with a quinoxaline core in the π-bridge and bulky aryl groups in the acceptor: Synthesis, properties, and femtosecond nonlinear optical activity of the chromophore/PMMA guest-host materials

Novel D-π-A chromophores with quinoxaline/quinoxalinone core in the π-conjugated bridge and various bulky groups in the acceptor moiety have been synthesized and systematically investigated at molecular level by UV–Vis spectroscopy, DFT calculations, electrochemical and TGA-DSC methods as well as at materials level by the example of PMMA-based composite polymer materials doped with different chromophore contents using molecular modeling and SHG technique. Chromophores exhibit positive dioxane/chloroform solvatochromic shift of ca. 50 nm, high values of first hyperpolarizability and dipole moment, small energy gap and good thermal stability. Tolyl and cyclohexylphenyl substituents unlike phenyl can be treated as most effective isolating groups, preventing chromophore pronounced aggregation even at 30 wt% content. Femtosecond nonlinear optical (NLO) activity was studied for poled thin guest-host polymer films with various chromophore weight content. Film DBA-VQPhV-TCFPhCy(25 wt%)/PMMA with bulky cyclohexylphenyl groups in chromophore acceptor shows maximal NLO coefficient, d33, values among the studied materials (37 pm/V) as well as good long-term stability of NLO response together with excellent chromophore thermal stability (Td = 256 °C). Composite materials doped with quinoxaline chromophores are photostable with respect to laser pulses with peak intensities up to 11 GW/cm2.

Thermodynamic favorable CO2 conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method

Organocatalysis represents a promising field in chemical fixation of CO2. Herein, a facile metal-free strategy was reported for the one-pot preparation of cyclic carbonates and α-hydroxy ketones from vicinal diols, propargylic alcohols and CO2. Wide scope of vicinal diols and propargylic alcohols was demonstrated to be efficient under the DBU-catalyzed conditions. A plausible mechanism was proposed, which included detailed main and side reactions under the metal-free conditions.

Synthesis of Α-hydroxy ketones by copper(I)-catalyzed hydration of propargylic alcohols: CO2 as a cocatalyst under atmospheric pressure

Inexpensive and efficient Cu(I) catalysis is reported for the synthesis of α-hydroxy ketones from propargylic alcohols, CO2, and water via tandem carboxylative cyclization and nucleophilic addition reaction. Notably, hydration of propargylic alcohols can be carried out smoothly under atmospheric CO2 pressure, generating a series of α-hydroxy ketones efficiently and selectively. This strategy shows great potential for the preparation of valuable α-hydroxy ketones by using CO2 as a crucial cocatalyst under mild conditions.

Selective Conversion of CO 2 and Switchable Alcohols into Linear or Cyclic Carbonates via Versatile Zinc Catalysis

It is promising and challenging to achieve the effective construction of carbonates using CO 2 and a non-noble metal catalyst. Herein, selective catalytic conversion of CO 2 and switchable alcohol candidates to produce linear or cyclic carbonates and α-hydroxy ketones via effective zinc catalyst was developed. A series of primary alcohols and cyclohexanol, 1,2-diols, and water can serve as nucleophiles to give alkyl or aryl 2-substituted-3-oxobutan-2-yl carbonates, substituted 1,3-dioxolan-2-ones, 3-substituted 3-hydroxybutan-2-ones, respectively with excellent selectivity and high yields.