1889-67-4

Usage

Uses

Used in Organic Synthesis:
2,3-Dimethyl-2,3-diphenyl butane is used as a building block in organic synthesis for the creation of a variety of other organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research Applications:
In the field of research, 2,3-Dimethyl-2,3-diphenyl butane is utilized as a model compound to study various chemical reactions and mechanisms. Its predictable reactivity and structural features make it an ideal candidate for probing the effects of steric hindrance and electronic influences in chemical processes.
Used in Chemical Industry:
2,3-Dimethyl-2,3-diphenyl butane finds applications in the chemical industry as a precursor to more complex molecules and materials. Its stability and reactivity make it suitable for use in the production of polymers, plastics, and other materials that require specific chemical and physical properties.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,3-Dimethyl-2,3-diphenyl butane is used as a starting material for the synthesis of drug candidates. Its unique structure can be modified to create new compounds with potential therapeutic effects, contributing to the development of novel medications.
Used in Material Science:
2,3-Dimethyl-2,3-diphenyl butane is also used in material science for the development of new materials with specific properties. Its chemical structure can be tailored to create materials with improved thermal stability, mechanical strength, or other desirable characteristics for various applications.

InChI:InChI=1/C18H22/c1-17(2,15-11-7-5-8-12-15)18(3,4)16-13-9-6-10-14-16/h5-14H,1-4H3

Synthetic route

1-methyl-1-phenylethyl alcohol (617-94-7) → dicumene (1889-67-4)

Conditions	Yield
With lithium aluminium tetrahydride; titanium(III) chloride In tetrahydrofuran Heating;	92%
With hydrogen bromide; zinc Reagens 4: Essigsaeure;
With hydrogenchloride; zinc Reagens 4: Essigsaeure;

isopropenylbenzene (98-83-9) → dicumene (1889-67-4) + 1-methyl-1-phenylethyl alcohol (617-94-7)

Conditions	Yield
With sodium tetrahydroborate; (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; oxygen In ethanol; benzene for 0.583333h; Ambient temperature;	A 8% B 92%
With sodium tetrahydroborate; oxygen; meso-tetraphenylporphyrin iron(III) chloride In methanol; benzene Ambient temperature;	A 41% B 40%

2-nitro-2-phenylpropane (3457-58-7) → Isopropylbenzene (98-82-8) + dicumene (1889-67-4)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran at 25℃; Product distribution; Mechanism;	A 8.8% B 91.2%
With potassium hydroxide; mercury In ethanol at 20℃; pH=13; Reduction; Electrolysis;	A 2 % Chromat. B 85 % Chromat.

benzoyl chloride (98-88-4) + Me4(PrO)4(μ-PrO)2W2 → dicumene (1889-67-4)

Conditions	Yield
In tetrahydrofuran -78 deg C to 66 deg C in 1 h; 66 deg C, 3 h;	90%

isopropenylbenzene (98-83-9) → dicumene (1889-67-4)

Conditions	Yield
With nitrous oxide; sodium tetrahydroborate; meso-tetraphenylporphyrin iron(III) chloride; tetramethyl ammoniumhydroxide In methanol; toluene for 14h; Reagent/catalyst; Time;	87%
Multi-step reaction with 4 steps 2: aq. NaOH / H2O 3: 47 percent / MgSO4, KMnO4 / acetone; H2O / 46 h / 25 - 30 °C 4: 9 percent / hexamethylphosphoric acid triamide / 45 h / Irradiation View Scheme

Isopropylbenzene (98-82-8) + 2,2-bis(tert-butylperoxy)butane (2167-23-9) → tert-butyl peroxyacetate (107-71-1) + dicumene (1889-67-4) + tert-butyl cumyl peroxide (3457-61-2) + acetone (67-64-1) + butanone (78-93-3) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 100℃; for 11h; Product distribution; Mechanism;	A 61% B 86% C 8% D 15% E 16% F 104 %
at 110℃; for 2h;

Isopropylbenzene (98-82-8) → dicumene (1889-67-4)

Conditions	Yield
With di-tert-butyl peroxide; sodium acetate at 120℃; for 10h; Schlenk technique; Green chemistry;	85%
With di-tert-butyl peroxide; sodium acetate at 120℃; for 10h;	85%
With trans-di-O-tert-butyl hyponitrite at 80℃; for 0.5h;	54.5%

methyl magnesium iodide (917-64-6) + Isopropylbenzene (98-82-8) + α-chloro-nitroso-2,2,6,6-tetramethylcyclohexane (62735-89-1) → 2,2,6,6-Tetramethylcyclohexanone oxime (7007-40-1) + dicumene (1889-67-4) + C11H21NO (76014-60-3) + 2,2,6,6-Tetramethyl-cyclohexanone O-(1-methyl-1-phenyl-ethyl)-oxime (76014-62-5)

Conditions	Yield
Product distribution; Mechanism; Investigation of the reaction of the title compound with Grignard and organolithium reagents. The effect of various solvents is examined.;	A 85% B 22% C 2% D 3%

methyl magnesium iodide (917-64-6) + α-chloro-nitroso-2,2,6,6-tetramethylcyclohexane (62735-89-1) → n-butyllithium (109-72-8, 29786-93-4) + dicumene (1889-67-4) + C11H21NO (76014-60-3) + 2,2,6,6-Tetramethyl-cyclohexanone O-(1-methyl-1-phenyl-ethyl)-oxime (76014-62-5)

Conditions	Yield
In various solvent(s)	A 85% B 22% C 2% D 3%

Isopropylbenzene (98-82-8) + α-chloro-nitroso-2,2,6,6-tetramethylcyclohexane (62735-89-1) → 2,2,6,6-Tetramethylcyclohexanone oxime (7007-40-1) + dicumene (1889-67-4) + C11H21NO (76014-60-3) + 2,2,6,6-Tetramethyl-cyclohexanone O-(1-methyl-1-phenyl-ethyl)-oxime (76014-62-5)

Conditions	Yield
	A 85% B 22% C 2% D 3%

isopropenylbenzene (98-83-9) → Isopropylbenzene (98-82-8) + dicumene (1889-67-4)

Conditions	Yield
With titanium(III) citrate; Tris buffer; tetra(n-butyl)ammonium hydroxide; vitamin B-12 In ethanol pH=8;	A 7% B 85%
With methanol for 2h; UV-irradiation;	A 11% B 79%
With C51H71CoN4O14(1+)*ClO4(1-); trifluoroacetic acid In acetonitrile at 20℃; Electrolysis; Inert atmosphere;	A 11% B 63%
With hydrogen In acetone at -78℃; under 2 Torr; for 0.5h;

cumenyl chloride (934-53-2) → dicumene (1889-67-4)

Conditions	Yield
With chlorotris(triphenylphosphine)cobalt(I) In benzene for 2h; Ambient temperature;	83%
Wurtz procedure;	30%

methyllithium (917-54-4) + acetophenone (98-86-2) → dicumene (1889-67-4)

Conditions	Yield
With <<(n-PrO)3WCl2>2> In tetrahydrofuran -78 deg C -> RT, 1 h, then reflux, 3 h;	83%

acetophenone (98-86-2) + Me4(PrO)4(μ-PrO)2W2 → dicumene (1889-67-4)

Conditions	Yield
In tetrahydrofuran -78 deg C to 66 deg C in 1 h; 66 deg C, 3 h;	83%

1,3-dioxoisoindolin-2-yl 2-methyl-2-phenylpropanoate → dicumene (1889-67-4)

Conditions	Yield
With C55H46N4O4W; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h; Irradiation;	83%

benzoic acid ethyl ester (93-89-0) + Me4(PrO)4(μ-PrO)2W2 → dicumene (1889-67-4)

Conditions	Yield
In tetrahydrofuran -78 deg C to 66 deg C in 1 h; 66 deg C, 3 h;	79%

phenylglyoxylic acid ethyl ester (1603-79-8) + 2-methyl-2-phenylpropionic acid (826-55-1) → dicumene (1889-67-4) + ethyl 2-hydroxy-3-methyl-2,3-diphenylbutanoate

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In dimethyl sulfoxide at 40℃; for 1h; Reagent/catalyst; Solvent; Glovebox; Inert atmosphere; Irradiation;	A 11% B 77%

cumenyl chloride (934-53-2) → Isopropylbenzene (98-82-8) + dicumene (1889-67-4)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran at 25℃; Product distribution; Mechanism;	A 23.9% B 76.1%
With dipotassium hydrogenphosphate; benzaldehyde; silver nitrate; zinc In water at 30℃; for 1h;	A 32% B 61%

2-nitro-2-phenylpropane (3457-58-7) + lithium 1-nitroethan-1-ide (28735-55-9) → dicumene (1889-67-4) + 2-phenyl-2-methyl-3-nitrobutane (65253-35-2)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide for 45h; Irradiation;	A 9% B 74%

chloro-trimethyl-silane (75-77-4) + 2-nitro-2-phenylpropane (3457-58-7) → dicumene (1889-67-4) + 2-phenyl-2-(trimethylsilyl)propane (18028-00-7)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran at 25℃; Product distribution; Mechanism;	A 73% B 1%

Isopropylbenzene (98-82-8) → dicumene (1889-67-4) + 1-methyl-1-phenylethyl alcohol (617-94-7)

Conditions	Yield
With sodium tetrahydroborate; tetramethyl ammoniumhydroxide; oxygen; polymer 1-A In methanol for 1h; Product distribution; various catalysts;	A 12% B 71%
With sodium tetrahydroborate; tetramethyl ammoniumhydroxide; oxygen; polymer 1-A In methanol for 1h;	A 12% B 71%
With sodium tetrahydroborate; tetramethyl ammoniumhydroxide; oxygen; (5-p-acetamidophenyl-10,15,20-triphenylporphinato)iron(III) chloride In methanol for 1h;	A 46% B 41%

Isopropylbenzene (98-82-8) + percarbonate de O,O-t-butyle et O-vinyle (85684-59-9) → 3-oxobutyraldehyde (625-34-3) + butanedial (638-37-9) + dicumene (1889-67-4) + acetaldehyde (75-07-0) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 140℃; for 3.5h; Product distribution; Mechanism; sealed tube;	A 15% B 10% C n/a D n/a E 25% F 69%

Isopropylbenzene (98-82-8) → dicumene (1889-67-4) + meso 2,3-bis(tert-butylthio)-2,3-diethyl-1,4-butanedinitrile (91734-14-4)

Conditions	Yield
With di-tert-butyl diperoxyoxalate; 2-(t-butylthio)acrylonitrile at 130℃; for 12h;	A 63% B 5%

dimethyl zinc(II) (544-97-8) + acetophenone (98-86-2) → dicumene (1889-67-4)

Conditions	Yield
Stage #1: dimethyl zinc(II) With vanadiumtetrachloride In tetrahydrofuran; hexane at 0℃; for 0.5h; complexation; Stage #2: acetophenone In tetrahydrofuran; hexane for 12h; Methylation; dimerization; Heating;	61%

Isopropylbenzene (98-82-8) + 1,3-dehydroadamantane (24569-89-9) → dicumene (1889-67-4) + 1,1'-Biadamantane (3732-31-8) + 2-(adamantan-1-yl)-2-phenylpropane

Conditions	Yield
at 110℃; for 1h; Inert atmosphere;	A 18% B 21% C 61%

Isopropylbenzene (98-82-8) + bis(1-methyl-1-phenylethyl)peroxide (80-43-3) → dicumene (1889-67-4)

Conditions	Yield
Stage #1: Isopropylbenzene; bis(1-methyl-1-phenylethyl)peroxide at 130℃; for 0.5h; Stage #2: With N,N-dimethyl-aniline at 130℃; for 8h; Temperature;	60.4%

benzoic acid anhydride (93-97-0) + Me4(PrO)4(μ-PrO)2W2 → dicumene (1889-67-4) + 1-methyl-1-phenylethyl alcohol (617-94-7)

Conditions	Yield
In tetrahydrofuran -78 deg C to 66 deg C in 1 h; 66 deg C, 3 h;	A 56% B 20%

isopropenylbenzene (98-83-9) → Isopropylbenzene (98-82-8) + dicumene (1889-67-4) + 1-methyl-1-phenylethyl alcohol (617-94-7)

Conditions	Yield
With sodium tetrahydroborate; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; oxygen In ethanol; benzene for 1h; Ambient temperature;	A 4% B 34% C 53%

isopropyl alcohol (67-63-0) + isopropenylbenzene (98-83-9) → dicumene (1889-67-4) + 2,4,5-Trimethyl-4,5-diphenyl-hexan-2-ol (103230-00-8) + H2

Conditions	Yield
With europium(III) chloride In methanol for 3h; Irradiation;	A 13% B 53% C n/a

2-methyl-2-phenylpropionic acid (826-55-1) → dicumene (1889-67-4)

Conditions	Yield
With C44H32N4(2+)*2F6P(1-); sodium hydroxide In water; acetonitrile at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Irradiation;	52%

dicumene (1889-67-4) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + acetophenone (98-86-2)

Conditions	Yield
With nitrosonium hexachloroantimonate In dichloromethane at 23℃; for 12h; Mechanism; Quantum yield; Product distribution; Irradiation; other solvent; other reactant; without irradiation;	A 90% B 2%
With nitrosonium hexachloroantimonate In dichloromethane at 23℃; for 12h; Irradiation;	A 90% B 2%

dicumene (1889-67-4) + 1,2,4,5-tetracyanobenzene (712-74-3) → Cumyl methyl ether (935-67-1) + 5-(1-methyl-1-phenylethyl)benzene-1,2,4-tricarbonitrile

Conditions	Yield
In methanol; acetonitrile for 4h; Irradiation;	A 50% B 87%

dicumene (1889-67-4) → isopropenylbenzene (98-83-9)

Conditions	Yield
With Nitrogen dioxide at -78℃; for 2h; Irradiation;	85%

dicumene (1889-67-4) → acetophenone (98-86-2)

Conditions	Yield
With naphthalene-1,4-dicarbonitrile; oxygen for 63h; Irradiation;	61%

Upstream product

• 109-65-9 1-bromo-butane 
• 109-72-8 n-butyllithium 
• 98-82-8 Isopropylbenzene 
• 110-05-4 di-tert-butyl peroxide 
• 110-22-5 diacetyl peroxide 
• 16066-38-9 di-n-propyl peroxydicarbonate 
• 2396-01-2 phenyl radical 
• 78-00-2 tetraethyllead(IV) 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 2901-13-5 ethyl 2-methyl-2-phenylpropionate 
• 106-93-4 ethylene dibromide 
• 623-26-7 terephthalonitrile 
• 127092-00-6 4-methoxybicumene 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 98-82-8 Isopropylbenzene 
• 30034-76-5 p,p'-dinitrobicumyl 
• 935-67-1 Cumyl methyl ether 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 130379-16-7 2-(trinitromethyl)-2-phenylpropane 
• 98-83-9 isopropenylbenzene 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 4794-07-4 2-phenylisopropyl radical 
• 16804-70-9 cumyl cation 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 3910-35-8 1,1,3-trimethyl-3-phenylindane 
• 84233-67-0 2-phenyl-1,2-propanediol dinitrate 
• 3003-91-6 cumyl potassium 

Relevant academic research and scientific papers

Solid-state photodecarbonylation of diphenylcyclopropenone: A quantum chain process made possible by ultrafast energy transfer

It has been reported that electronic excitation of diphenylcyclopropenone (DPCP) into the second excited state (S2) results in an adiabatic ring-opening process within 200 fs to give an excited product with a lifetime of ca. 8 ps in S2. Knowing that energy transfer in crystals may occur within 1-2 ps, we recognized that the conditions could be right for a quantum chain process with the excited-state product sensitizing a neighboring ground-state reactant to set up a domino effect. In agreement with that, we discovered that excitation or macroscopic crystals result in a remarkably efficient reaction to give diphenylacetylene as a polycrystalline powder by a process that releases a great deal of mechanical energy. By taking advantage of nanocrystalline suspensions and using dicumyl ketone as an internal actinometer and after accounting for differences in absorbance at the irradiation wavelength, we were able to establish that the quantum yield of the reaction for DPCP was ΦDPCP = 3.30 ± 0.35, which is well above unity and consistent with a remarkable quantum chain process. Copyright

The electrochemical reduction of α-nitrocumene in a protic and basic medium on large surface area (porous) electrodes: Electronation-protonation or electrocatalytic hydrogenation?

The electrochemical reduction of α-nitrocumene (1) has been investigated under controlled potential, at a mercury pool cathode and at Raney metal (Raney nickel, Raney cobalt and Devarda copper) and fractal nickel electrodes in basic aqueous ethanol. A comparison of the product distribution from the reduction at Hg (electronation-protonation (EP) mechanism) and that from the reduction at Raney metals and fractal nickel has shown that both the electrocatalytic hydrogenation (ECH) and EP mechanisms can be involved at large surface area (porous) transition metal electrodes in a basic protic medium. Cyclic voltammetry was used to determine the reduction potential of 1 at Hg and at bright polycrystalline nickel, cobalt, and copper cathodes in the same medium.

Photo-Fries reaction in water made selective with a capsule

The water soluble capsule formed by a deep cavity cavitand with eight carboxylic acid groups controls product distribution during photo-Fries rearrangement of naphthyl esters in water by restricting the mobility of primary singlet radical pair. The Royal Society of Chemistry.

Large-scale photochemical reactions of nanocrystalline suspensions: A promising green chemistry method

Photochemical reactions in the solid state can be scaled up from a few milligrams to 10 grams by using colloidal suspensions of a photoactive molecular crystal prepared by the solvent shift method. Pure products are recovered by filtration, and the use of H2O as a suspension medium makes this method a very attractive one from a green chemistry perspective. Using the photodecarbonylation of dicumyl ketone (DCK) as a test system, we show that reaction efficiencies in colloidal suspensions rival those observed in solution.

The Thermal Decomposition of 1-Methyl-1-phenylethyl 2,2-Dimethylperoxypropionate in Cumene

The thermal decomposition of 1-methyl-1-phenylethyl 2,2-dimethylperoxypropionate was studied in cumene.Based on the kinetic parameters and the decomposition products, it was concluded that the peroxyester was decomposed mainly by means of the radical process in cumene.

Enhanced cage effects in supercritical fluid solvents. The behavior of diffusive and geminate caged-pairs in supercritical carbon dioxide

The behavior of geminate and diffusive radical caged-pairs arising from the photolysis of dicumyl ketone in conventional and supercritical carbon dioxide (SC-CO2) solvents has been examined. The results suggest that locally enhanced solvent density about a solute (solvent/solute clustering) can lead to an enhanced cage effect near the critical pressure in supercritical fluid solvents. This enhanced cage effect is similar in magnitude for both diffusive and geminate caged-pairs.

Molecular rearrangement. 36. Selective α-CH oxidation of alkylarenes by nitrogen dioxide on thermolysis with nitramines

Thermolysis of 2,4,6-trichloro-N-nitroaniline 1 and N-methyl-2,4-dinitro-N- nitroaniline 2 each with primaryl alkylbenzenes led to the formation of acylbenzenes. Similar reactions with secondary alkylbenzenes afforded a mixture of acetophenone and aliphatic aldehydes. Use of tert-butylbenzene in this reaction yielded formaldehyde and 2,3-diphenyl-2,3-dimethylbutane. The mechanisms of the studied reactions are discussed.

Oxidation of Isopropylbenzene by Iron Tetraphenylporphyrin: Evidence for the Interaction of the Cumyl Radical with Oxygen Donors

Evidence is presented for an unprecedented oxygen transfer from oxygen donors to a cumyl radical in the oxidation of isopropylbenzene catalysed by tetraphenyl metalloporphyrins.

Synthesis and Thermal Decomposition of Di-t-Butyl Peroxydicarbonate

Di-t-butyl peroxydicarbonate(DBPD) has been synthesized in a novel route and thermally decomposed at 40-70 deg C.The decomposition exhibits first-order kinetics and the values of ΔH* and ΔS* are 122 kJ mol-1 and 46 J K-1 mol-1, respectively. 2-Methyl-2-propanol is obtained quantitatively as a decomposition product and the rates are a little dependant on the viscosities of solvents, normal alkanes.The mechanism that involves the initial scission of the O-O bond is discussed and the values of the rates and the activation parameters of DBPD are compared withthose of diacetyl peroxide and dibenzoyl peroxide.

Carbon Acidity. 67. The Indicator Scale of Cesium Ion Pairs in Tetrahydrofuran

An equilibrium cesium ion-pair indicator scale relative to 9-phenylfluorene at pKa = 18.49 has been established for 22 hydrocarbons in tetrahydrofuran.Comparison of this scale to those developed in Me2So and DME shows the scale to be independent of solvent.Visible absorbance spectral characteristics of the indicator anions are also reported and discussed in relation to other solvents.Thermodynamic studies of the equilibrium reactions were carried out over a temperature range of -20 to 25 deg C and reveal the importance of internal rotation on the entropy of reactions.Thermodynamic constants found for reaction between fluorenes show a complex behavior and are generally not interpretable at this time.