2,2-DIMETHYL-3-PENTANONE CAS#: 564-04-5; ChemWhat Code: 798923

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name2,2-DIMETHYL-3-PENTANONE
IUPAC Name2,2-dimethylpentan-3-one
Molecular StructureStructure of 2,2-Dimethyl-3-pentanone CAS 564-04-5
CAS Registry Number 564-04-5
EINECS NumberNo data available
MDL NumberMFCD00039918
Beilstein Registry NumberNo data available
Synonyms2,2-dimethyl-3-pentanone, 2,2-dimethylpentan-3-one, tert-butyl ethyl ketone, 2,2-dimethylpent-3-one, t-butyl ethyl ketone, 4,4-dimethyl-3-pentanone, ethyl tert-butyl ketone
CAS Number 564-04-5
CAS NO 564-04-5
Molecular FormulaC7H14O
Molecular Weight114.186
InChIInChI=1S/C7H14O/c1-5-6(8)7(2,3)4/h5H2,1-4H3
InChI KeyVLNUTKMHYLQCQB-UHFFFAOYSA-N
Canonical SMILESCCC(=O)C(C)(C)C
Patent Information
Patent IDTitlePublication Date
US4240983 Monohalogenated ketones 1980

Physical Data

AppearanceNo data available
SolubilityIt is soluble in water as well as soluble in alcohol, benzene.
Refractive index1.4028
Melting Point, °C Solvent (Melting Point)
123
122 – 127
-49
Refractive Index Wavelength (Refractive Index), nm Temperature (Refractive Index), °C
1.403758920
1.405 589 20
1.4028 589 25
1.403 589 25
1.4109 589 20
1.4057 589 20
1.4049 589 20
Boiling Point, °CPressure (Boiling Point), Torr
118 – 125 3
125 759.8
123 – 126 720
79 157
68 – 69 12
124 – 125 680
124.5 730
125 – 126 769
Density, g·cm-3Reference Temperature, °CMeasurement Temperature, °C
0.811420
0.8098 420
0.8017 2525
0.8258 00
0.8106 020
0.81 021
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Association with compound CCl4282.6-dimethylphenol
Association with compound CCl4 282,5-Dimethylphenol
Association with compound CCl4 28phenol
Association with compound CCl4 284-chloro-phenol
Association with compound CCl4 283,5-dichlorophenol
Association with compound CCl4 282-monochlorophenol
Association with compound CCl4 282-hydroxybromobenzene
Association with compound CCl4 282,4,6-Trichlorophenol
Association with compound CCl4 282-Iodophenol

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1H chloroform-d1 400
Chemical shifts 13Cchloroform-d1 101
Chemical shifts 1Hchloroform-d1
Chemical shifts, Spectrum 1Hchloroform-d1 500
Chemical shifts, Spectrum 13Cchloroform-d1 125
Chemical shifts1HCDCl3 300
1HCDCl3 300
Chemical shifts 13CCDCl3 75
Chemical shifts1H
13Cbenzene-d6
Spin-spin coupling constants benzene-d6
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Mid IR (MIR), Bands film
Bands neat (no solvent)1710 cm**(-1)
Bands hexane1715 cm**(-1)
Bands CCl4 1711 cm**(-1)
Bands tetrahydrofuran1715 cm**(-1)
Description (Mass Spectrometry) Comment (Mass Spectrometry)
electron impact (EI), gas chromatography mass spectrometry (GCMS), spectrum
chemical ionization (CI), spectrum
fragmentation pattern, spectrum MIKE (mass ion kinetic energy)
metastable ions, collisional activation
spectrum
fragmentation pattern collisional activation
negative ion spectroscopy
spectrum collisional activation
metastable ions
spectrum, electron impact (EI) charge exchange with positive ions
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nm
UV/VIS
Spectrum diethyl ether 260 – 310 nm
Absorption maximahexane 232, 290
Absorption maxima ethanol 284
Absorption maxima H2O279

Route of Synthesis (ROS)

Route of Synthesis(ROS) of 2,2-DIMETHYL-3-PENTANONE CAS#: 564-04-5
ConditionsYield
Stage #1: N-cyclohexyl-2,2-dimethylpropanamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.5h;
Stage #2: ethylmagnesium bromide With cerium(III) chloride In tetrahydrofuran; dichloromethane at -78℃; for 2h;
Stage #3: With hydrogenchloride In ethyl acetate
Experimental Procedure
General procedure: Tf2O (185μL, 1.1mmol) was added dropwise to a cooled (0°C) solution of amide (1.0mmol) and 2-fluoropyridine (103μL, 1.2mmol) in dichloromethane (4mL). After stirring at 0°C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at −78°C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25percent, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt.
n/a
74%
More: Inquiry all available synthetic routes with detailed experimental procedures

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH319 (95.83%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Hazardous to the aquatic environment, long-term hazard]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP264, P280, P305+P351+P338, and P337+P313
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationNot dangerous goods
Under the room temperature and away from light
HS Code291419
StorageUnder the room temperature and away from light
Shelf LifeNo data available
Market PriceUSD
Use Pattern
2,2-DIMETHYL-3-PENTANONE CAS#: 564-04-5 is commonly used as an intermediate in the synthesis of perfumes.

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