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| CAS No.: | 4249-10-9 |
|---|---|
| Name: | 1,2,3,4-Tetramethyl-1,3-cyclopentadiene |
| Molecular Structure: | |
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| Formula: | C9H14 |
| Molecular Weight: | 122.21 |
| Synonyms: | Cyclopentadiene,1,2,3,4-tetramethyl- (7CI);1,2,3,4-Tetramethylcyclopentadiene; |
| Density: | 0.83 g/cm3 |
| Boiling Point: | 146.816 °C at 760 mmHg |
| Flash Point: | 27.51 °C |
| Appearance: | light yellow liquid |
| Hazard Symbols: | R10:; |
| Risk Codes: | 10 |
| Safety: | 16 |
| Transport Information: | UN 3295 3/PG 3 |
| PSA: | 0.00000 |
| LogP: | 3.06290 |
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2,3,4,5-tetramethylcyclopent-2-en-1-ol
- 4249-10-9
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; |
- 164528-21-6
(C5Me4H)2Yb(THF)2
- 49673-43-0
N1,N2-bis(2,6-dimethylphenyl)ethane-1,2-diimine
A
- 4249-10-9
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% |
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2,3,4,5-tetramethyl-2-cyclopenten-1-one
- 4249-10-9
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 |
- 49587-60-2
(2E,5E)-3,5-dimethylhepta-2,5-dien-4-ol
B
- 4249-10-9
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 |
- 164528-21-6
(C5Me4H)2Yb(THF)2
A
- 4249-10-9
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% |
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1,1,2,3-Tetramethyl-4-methylen-cyclobuten-(2)
- 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene
| Conditions | Yield |
|---|---|
| With sulfuric acid In tetrachloromethane |
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dimethyl sulfate
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sodium cyclopentadienylide
- 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene
| Conditions | Yield |
|---|---|
| With sodium amide In ammonia |
- 73659-32-2
1,2,3,4-Tetramethyl-cyclopent-3-enol
A
- 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene
B
- 10060-55-6
1,2,3,5-tetramethylcyclopenta-1,3-diene
C
- 10060-56-7
1,3,4,5-tetramethylcyclopenta-1,3-diene
| Conditions | Yield |
|---|---|
| Heating; Title compound not separated from byproducts; |
- 90002-77-0
1-chloro-1,3,4-trimethyl-2-methylene-3-cyclobutene
- 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: diethyl ether 2: H2SO4 / CCl4 View Scheme |
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Specification
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%.
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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%.
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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