2,3,4,5-tetramethylcyclopent-2-en-1-ol
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With Dandong Pearl-H type cation exchange resin In diethyl ether at 25℃; Reagent/catalyst; | 82% |
With sulfuric acid at 50℃; for 0.5h; Temperature; | 55.3% |
toluene-4-sulfonic acid In diethyl ether for 0.333333h; Ambient temperature; Yield given; | |
With toluene-4-sulfonic acid In benzene Ambient temperature; Yield given; | |
With iodine In diethyl ether Yield given; |
(C5Me4H)2Yb(THF)2
N1,N2-bis(2,6-dimethylphenyl)ethane-1,2-diimine
A
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Stage #1: (C5Me4H)2Yb(THF)2; N1,N2-bis(2,6-dimethylphenyl)ethane-1,2-diimine In tetrahydrofuran at 40℃; for 0.5h; Schlenk technique; Glovebox; Stage #2: In toluene at 60℃; for 5h; Schlenk technique; Glovebox; | A 78% B 49% |
2,3,4,5-tetramethyl-2-cyclopenten-1-one
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; sulfuric acid Heating; | 75% |
Stage #1: 2,3,4,5-tetramethyl-2-cyclopenten-1-one With lithium aluminium tetrahydride In diethyl ether for 2h; Stage #2: With hydrogenchloride; air In diethyl ether; water for 16h; | 37% |
Multi-step reaction with 2 steps 1: LiAlH4 2: p-TsOH / benzene / Ambient temperature View Scheme | |
With sodium tetrahydroborate In ethanol |
(2E,5E)-3,5-dimethylhepta-2,5-dien-4-ol
B
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; water at 20℃; for 2 - 4h; | A 15% B 75% |
Conditions | Yield |
---|---|
With methyllithium In diethyl ether Schlenk technique; | A 68% B n/a C n/a |
(C5Me4H)2Yb(THF)2
A
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Stage #1: (C5Me4H)2Yb(THF)2; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene In tetrahydrofuran at 40℃; for 0.5h; Schlenk technique; Glovebox; Stage #2: In toluene at 60℃; for 4h; Schlenk technique; Glovebox; | A 64% B 35% C 10% |
1,1,2,3-Tetramethyl-4-methylen-cyclobuten-(2)
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With sulfuric acid In tetrachloromethane |
dimethyl sulfate
sodium cyclopentadienylide
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With sodium amide In ammonia |
1,2,3,4-Tetramethyl-cyclopent-3-enol
A
1,2,3,4-tetramethylcyclopenta-1,3-diene
B
1,2,3,5-tetramethylcyclopenta-1,3-diene
C
1,3,4,5-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Heating; Title compound not separated from byproducts; |
1-chloro-1,3,4-trimethyl-2-methylene-3-cyclobutene
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: H2SO4 / CCl4 View Scheme |
2,3,5,6-tetrahydro-2,3,5,6-tetramethyl-γ-pyrone
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / p-TsOH / toluene 2: 75 percent / LiAlH4; aq. H2SO4 / Heating View Scheme |
(E)-4-methylhex-4-en-3-one
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 54 percent / KOH / methanol 2: 75 percent / p-TsOH / toluene 3: 75 percent / LiAlH4; aq. H2SO4 / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 57 percent / KOH / methanol 2: 54 percent / KOH / methanol 3: 75 percent / p-TsOH / toluene 4: 75 percent / LiAlH4; aq. H2SO4 / Heating View Scheme |
2,3,4-trimethylcyclopent-2-enone
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: Heating View Scheme |
2,3,4,5-tetramethylcyclopent-2-en-1-ol
1,2,3,4-tetramethylcyclopenta-1,3-diene
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
In pentane |
methylene chloride
1,2,3-trimethylcyclopentadiene
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With sodium hydroxide |
bromomethyldimethylsilyl chloride
A
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; Inert atmosphere; Schlenk technique; Reflux; |
Conditions | Yield |
---|---|
In benzene at 30℃; for 4h; | 99% |
Conditions | Yield |
---|---|
With sodium hydride for 24h; Reflux; | 98.1% |
Conditions | Yield |
---|---|
at 80℃; Inert atmosphere; neat (no solvent); | 98% |
decacarbonyldirhenium(0)
1,2,3,4-tetramethylcyclopenta-1,3-diene
tricarbonyl(η5-tetramethylcyclopentadienyl)rhenium
Conditions | Yield |
---|---|
at 150 - 210℃; for 5.66667h; Inert atmosphere; Schlenk technique; | 98% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.0833333h; | 97% |
Conditions | Yield |
---|---|
With potassium hydride for 24h; Reflux; | 96.5% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
ethenetetracarbonitrile
5,5,6,6-tetracyano-1,2,3,4-tetramethylbicyclo<2.2.1>hept-2-ene
Conditions | Yield |
---|---|
In benzene at 25℃; Thermodynamic data; ΔH; | 96% |
In benzene for 1.5h; | 96% |
In 1,4-dioxane at 25℃; Rate constant; Thermodynamic data; ΔH; |
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With sodium hydride; aniline In tetrahydrofuran at 50℃; for 2.5h; Stage #2: chlorodimethyl(4-methoxyphenyl)silane In tetrahydrofuran; toluene at 0 - 20℃; | 95.5% |
Conditions | Yield |
---|---|
at 100℃; for 6h; Diels-Alder reaction; neat (no solvent); stereoselective reaction; | 95% |
di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I)
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
In methanol; toluene at 23℃; | 95% |
Conditions | Yield |
---|---|
at 20℃; under 15201 Torr; for 12h; Inert atmosphere; Schlenk technique; | 93% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.0833333h; Kinetics; Solvent; | 93% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.0833333h; | 91% |
triisopropoxytitanium(IV) chloride
1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane Ar-atmosphere; addn. of BuLi (in hexane) to C5HMe4 (in THF, 0°C), warming to room temp., stirring (6 h), dropwise addn. of Ti-complex (in THF, -78°C), warming to room temp., stirring (12 h); solvent removal (vac.), extn. (pentane), filtration (Celite), solvent removal (vac.), chromy. (Bio-Beads); distillable (125-135°C, 1E-3 Torr); elem. anal.; | 90% |
n-butyllithium
isopropyldimethylsilyl chloride
1,2,3,4-tetramethylcyclopenta-1,3-diene
5-(isopropyldimethylsilyl)-1,2,3,4-tetramethylcyclopenta-1,3-diene
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; 1,2,3,4-tetramethylcyclopenta-1,3-diene In tetrahydrofuran; hexane Stage #2: isopropyldimethylsilyl chloride In tetrahydrofuran; hexane | 89% |
Conditions | Yield |
---|---|
at 130℃; Inert atmosphere; neat (no solvent); | 89% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
Chlorodimethyl-(2,4,6-trimethylphenyl)silane
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With sodium hydride; aniline In tetrahydrofuran at 50℃; for 2h; Stage #2: Chlorodimethyl-(2,4,6-trimethylphenyl)silane In tetrahydrofuran; toluene at 0 - 20℃; | 87.3% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
N-(4-bromophenyl)maleimide
1,2,3,4-tetramethylbicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic acid p-bromophenylimide
Conditions | Yield |
---|---|
In 1,4-dioxane at 25℃; Rate constant; Thermodynamic data; activation enthalpy ΔH(excit.) and entropy ΔS(excit.); | 87% |
In 1,4-dioxane | 87% |
at 25℃; Rate constant; |
1,2,3,4-tetramethylcyclopenta-1,3-diene
dimethyl(2-phenylethyl)chlorosilane
1,2,3,4-tetramethyl-5-(dimethylphenethylsilyl)cyclopenta-1,3-diene
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In hexane Stage #2: dimethyl(2-phenylethyl)chlorosilane In tetrahydrofuran | 87% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
chlorodimethyl(3,5-dimethylphenyl)silane
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With sodium hydride; aniline In tetrahydrofuran at 50℃; for 2h; Stage #2: chlorodimethyl(3,5-dimethylphenyl)silane In tetrahydrofuran; toluene at 0 - 20℃; | 87% |
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With sodium hydride; aniline In tetrahydrofuran at 50℃; for 2h; Stage #2: chlorodimethyl(3,5-dimethylphenyl)silane In tetrahydrofuran; toluene at 0 - 20℃; | 87% |
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With sodium hydride; aniline In tetrahydrofuran at 50℃; for 2h; Stage #2: chloromethyldiphenylsilane In tetrahydrofuran; toluene at 20 - 35℃; | 86.5% |
[2-(allyloxy)-3-tert-butyl-5-methylphenyl](chloro)dimethylsilane
1,2,3,4-tetramethylcyclopenta-1,3-diene
[2-(allyloxy)-3-tert-butyl-5-methylphenyl](dimethyl)(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silane
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With sodium hydride; aniline In tetrahydrofuran at 50℃; Stage #2: [2-(allyloxy)-3-tert-butyl-5-methylphenyl](chloro)dimethylsilane In tetrahydrofuran; toluene at 20℃; for 1h; Further stages.; | 86% |
1,2-bis-(chlorodimethylsilyl)ethane
1,2,3,4-tetramethylcyclopenta-1,3-diene
1,1'-<1,2-Ethandiylbis(dimethylsilyl)>bis(2,3,4,5-tetramethyl-2,4-cyclopentadien)
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 3h; Stage #2: 1,2-bis-(chlorodimethylsilyl)ethane In tetrahydrofuran; hexane for 8h; Heating; | 85% |
With n-butyllithium In tetrahydrofuran; hexane for 24h; Heating; | 72% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
[(η5-teramethylcyclopentadienyl)Sc(III)(o-dimethylaminobenzyl)2]
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: CH3C6H4NMe2; 1 equiv. of H2C5Me4 at 70°C; | 85% |
Os(hydride)6(triisopropylphosphine)2
1,2,3,4-tetramethylcyclopenta-1,3-diene
[OsH3(η5-tetramethylcyclopentadienyl)(P(i-Pr)3)]
Conditions | Yield |
---|---|
In octane byproducts: P(i-Pr)3, hydrogen; using Schlenk techniques; treatment of soln. of OsH6(P(i-Pr)3)2 in n-octane with 6 equiv. of tetramethylcyclopentadiene, reflux for 4 h; filtration, removal of solvent in vac.; as oil; | 85% |
OsH3Cl(PPh3)3
1,2,3,4-tetramethylcyclopenta-1,3-diene
[(η5-C5Me4H)OsCl(PPh3)2]
Conditions | Yield |
---|---|
In toluene (N2); std. Schlenk technique; mixt. of diene (1.5 equiv.) and Os complexin toluene was refluxed for 4 h; evapd. (vac.); washed (hexane, Et2O); dried (vac.); elem. anal.; | 84.1% |
1,2,3,4-tetramethylcyclopenta-1,3-diene
phenyldimethylsilyl chloride
1,2,3,4-tetramethyl-5-(dimethylphenylsilyl)cyclopenta-1,3-diene
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In hexane Stage #2: phenyldimethylsilyl chloride In tetrahydrofuran | 84% |
maleiimide
1,2,3,4-tetramethylcyclopenta-1,3-diene
1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
In benzene for 6h; Diels-Alder reaction; Heating; | 84% |
In methanol at 22℃; under 760.051 Torr; Kinetics; |
1,2,3,4-tetramethylcyclopenta-1,3-diene
dimethylsilicon dichloride
1-(chlorodimethylsilyl)-2,3,4,5-tetramethylcyclopenta-2,4-diene
Conditions | Yield |
---|---|
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In diethyl ether; hexane Stage #2: dimethylsilicon dichloride In tetrahydrofuran | 83% |
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In tetrahydrofuran at -78 - 20℃; Schlenk technique; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at 20℃; Schlenk technique; | 83% |
Stage #1: 1,2,3,4-tetramethylcyclopenta-1,3-diene With n-butyllithium In tetrahydrofuran at -78 - 20℃; Schlenk technique; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at -78 - 20℃; Schlenk technique; | 83% |
The 1,2,3,4-Tetramethyl-1,3-cyclopentadiene with cas registry number of 4249-10-9, belongs to the following product categories: (1)Alkenes; (2)Cyclic; (3)Organic Building Blocks. Its systematic name and IUPAC name are the same, which is 1,2,3,4-tetramethylcyclopenta-1,3-diene.
Physical properties about this chemical are: (1)ACD/LogP: 4.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.15; (4)ACD/LogD (pH 7.4): 4.15; (5)ACD/BCF (pH 5.5): 836.73; (6)ACD/BCF (pH 7.4): 836.73; (7)ACD/KOC (pH 5.5): 4301.18; (8)ACD/KOC (pH 7.4): 4301.18; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.47; (14)Molar Refractivity: 41.08 cm3; (15)Molar Volume: 147.2 cm3; (16)Polarizability: 16.28×10-24cm3; (17)Surface Tension: 22.6 dyne/cm; (18)Enthalpy of Vaporization: 36.8 kJ/mol; (19)Vapour Pressure: 5.76 mmHg at 25°C.
Preparation: this chemical can be prepared by 2,3,4,5-tetramethyl-2-cyclopentenone (cis+trans). This reaction will need reagent LiAlH4
aq. H2SO4. The yield is about 75%.
Uses of 1,2,3,4-Tetramethyl-1,3-cyclopentadiene: it can be used to produce 5,5,6,6-tetracyano-1,2,3,4-tetramethylbicyclo[2.2.1]hept-2-ene. This reaction will need reagent benzene with reaction temperature of 25 ℃. The yield is about 96%.
When you are using this chemical, please be cautious about it as the following:
The 1,2,3,4-Tetramethyl-1,3-cyclopentadiene is flammable, so keep it away from sources of ignition.
You can still convert the following datas into molecular structure:
(1)SMILES: C1(=C(/C(=C(/C)C1)C)C)\C;
(2)InChI: InChI=1/C9H14/c1-6-5-7(2)9(4)8(6)3/h5H2,1-4H3;
(3)InChIKey: VNPQQEYMXYCAEZ-UHFFFAOYAA;
(4)Std. InChI: InChI=1S/C9H14/c1-6-5-7(2)9(4)8(6)3/h5H2,1-4H3;
(5)Std. InChIKey: VNPQQEYMXYCAEZ-UHFFFAOYSA-N
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