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Name	1,2,3,4-Tetramethyl-1,3-cyclopentadiene	EINECS	N/A
CAS No.	4249-10-9	Density	0.83 g/cm³
PSA	0.00000	LogP	3.06290
Solubility	N/A	Melting Point	N/A
Formula	C₉H₁₄	Boiling Point	146.816 °C at 760 mmHg
Molecular Weight	122.21	Flash Point	27.51 °C
Transport Information	UN 3295 3/PG 3	Appearance	light yellow liquid
Safety	16	Risk Codes	10
Molecular Structure		Hazard Symbols	R10:;
Synonyms	Cyclopentadiene,1,2,3,4-tetramethyl- (7CI);1,2,3,4-Tetramethylcyclopentadiene;	Article Data	25

1,2,3,4-Tetramethyl-1,3-cyclopentadiene 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

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

B: C31H41N2OYb

Conditions

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%

: 54458-61-6
2,3,4,5-tetramethyl-2-cyclopenten-1-one

: 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions

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

A: chlorotetramethylcyclopentene

B: 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

: 90644-55-6
1,1,2,3-Tetramethyl-4-methylen-cyclobuten-(2)

: 4249-10-9
1,2,3,4-tetramethylcyclopenta-1,3-diene

Conditions

Conditions	Yield
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

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

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

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: H2SO4 / CCl4 View Scheme

1,2,3,4-Tetramethyl-1,3-cyclopentadiene 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

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