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4249-10-9

Basic Information
CAS No.: 4249-10-9
Name: 1,2,3,4-Tetramethyl-1,3-cyclopentadiene
Article Data: 25
Molecular Structure:
Molecular Structure of 4249-10-9 (1,2,3,4-Tetramethyl-1,3-cyclopentadiene)
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
Synthetic route
82061-20-9

2,3,4,5-tetramethylcyclopent-2-en-1-ol

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions
ConditionsYield
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

B

C31H41N2OYb

Conditions
ConditionsYield
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%
54458-61-6

2,3,4,5-tetramethyl-2-cyclopenten-1-one

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions
ConditionsYield
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

A

chlorotetramethylcyclopentene

B

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; water at 20℃; for 2 - 4h;A 15%
B 75%

N’-(2,3,4,5-tetramethylcyclopent-2-ene-ylidene)tosylhydrazide

A

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

B

C9H12S

C

7727-37-9

nitrogen

Conditions
ConditionsYield
With methyllithium In diethyl ether Schlenk technique;A 68%
B n/a
C n/a
164528-21-6

(C5Me4H)2Yb(THF)2

1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene

A

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

B

C41H61N2OYb

C

C27H39Yb

Conditions
ConditionsYield
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%
90644-55-6

1,1,2,3-Tetramethyl-4-methylen-cyclobuten-(2)

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions
ConditionsYield
With sulfuric acid In tetrachloromethane
77-78-1

dimethyl sulfate

4984-82-1

sodium cyclopentadienylide

4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%.

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