1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene supplier

Name
1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene
EINECS 229-723-1
CAS No. 6683-46-1
Article Data28
CAS DataBase
Density 0.883 g/cm³
Solubility
Melting Point 115-120℃
Formula C₁₄H₂₀
Boiling Point 250.6 °C at 760 mmHg
Molecular Weight 188.313
Flash Point 101.2 °C
Transport Information
Appearance
Safety 23-26-36/37/39
Risk Codes 20/21-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene;1,1,4,4-Tetramethyltetralin;NSC 17400;
PSA 0.00000
LogP 4.03560

Synthetic route

: 110-03-2
2,5-dimethyl-2,5-hexanediol

: 71-43-2
benzene

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
With aluminium trichloride at 55℃; for 6h;	99%

: 6223-78-5
2,5-dichloro-2,5-dimethyl hexane

: 71-43-2
benzene

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
With aluminum (III) chloride for 16h; Reflux;	91%
With aluminum (III) chloride for 16h; Reflux; Inert atmosphere;	88%
With aluminum (III) chloride Friedel-Crafts Alkylation; Reflux; Inert atmosphere;	82%

: 6223-78-5
2,5-dichloro-2,5-dimethyl hexane

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
With bromine; sodium hydrogencarbonate; aluminium trichloride In benzene	63%
In aluminium trichloride; benzene
In aluminium trichloride; benzene
In aluminium trichloride; benzene
In aluminium trichloride; benzene

: (η-cyclopentadienyl)(C10H8(CH3)4)(PF6)iron

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
In diethyl ether Pyrolysis of the Fe compd. by heating in vacuo, collecting the volatiles on a cold finger at -78°C.; The yellowish sublimate is dissolved in Et2O and purified (alumina), the solvent is removed to afford a clear colourless oil.;	45%

: 97595-53-4
1,1,4,4-Tetramethyl-tetralon-(2)-aethylenthioketal

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
With nickel In ethanol

: 51510-58-8
2,5-Dimethyl-5-phenyl-2-hexanol

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
With sulfuric acid

: 7446-70-0
aluminium trichloride

: 110-03-2
2,5-dimethyl-2,5-hexanediol

: 71-43-2
benzene

A: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

B: 22306-30-5
1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydroanthracene

...Expand

: 7446-70-0
aluminium trichloride

: 6223-78-5
2,5-dichloro-2,5-dimethyl hexane

: 71-43-2
benzene

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
mit viel AlCl3; dann bei Siedetemperatur; reagiert Analog mit anderen aromatischen Kohlenwasserstoffen;

...Expand

: 1,1,4,4-tetramethyl-decahydro-naphthalene

: 71-43-2
benzene

platinum-coal: platinum-coal

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
at 350 - 375℃;

...Expand

: 110-03-2
2,5-dimethyl-2,5-hexanediol

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. HCl, HCl gas / 0.25 h / 0 °C 2: 81.9 percent / AlCl3 / 24 h / Heating View Scheme
Multi-step reaction with 2 steps 1: HCl 2: AlCl3 View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol 2: aluminum (III) chloride View Scheme

: 117259-83-3
methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]benzoate

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 1h; Heating;	99%
With aluminium trichloride In dichloromethane for 0.25h; Heating;	96%
With aluminum (III) chloride In dichloromethane at 20℃;	58%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 75-36-5
acetyl chloride

: 17610-21-8
1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethanone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane for 2h; Reflux;	98%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 8h; Friedel-Crafts Acylation; Inert atmosphere;	96%
With aluminum (III) chloride	92%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 132392-26-8
5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-sulfonyl chloride

Conditions

Conditions	Yield
With chlorosulfonic acid In dichloromethane at 0℃; for 1h;	98%
With chlorosulfonic acid for 3h; Ambient temperature;
With chlorosulfonic acid at 0 - 20℃; for 3h;
With chlorosulfonic acid at 10 - 20℃; for 2h;

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 17610-21-8
1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethanone

Conditions

Conditions	Yield
Stage #1: acetyl chloride With aluminum (III) chloride In dichloromethane at 0℃; for 0.0833333h; Stage #2: 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene In dichloromethane at 20℃; for 3h;	98%

: 1190848-41-9
methyl 4-(chlorocarbonyl)-2-fluorobenzoate

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: methyl 2-fluoro-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane; benzene for 0.25h;	96%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 102121-55-1
1,1,4,4-tetramethyl-6-nitro-1,2,3,4-tetrahydro-naphthalene

Conditions

Conditions	Yield
With nitric acid In acetic anhydride at 0 - 20℃; Inert atmosphere;	92%
With nitric acid; acetic anhydride at 20℃; for 2h;	77%
With sulfuric acid; nitric acid In water at -10℃; for 1h;	76%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 27452-17-1
6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

Conditions

Conditions	Yield
With boron trifluoride-tetrahydrofuran complex; bromine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	92%
With N-Bromosuccinimide; toluene-4-sulfonic acid In methanol at 55℃; for 48h; Inert atmosphere;	79%
With boron trifluoride diethyl etherate; bromine In dichloromethane at 0 - 20℃; Inert atmosphere;	78%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 4755-77-5
Ethyl oxalyl chloride

: 142675-64-7
ethyl 2-oxo-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetate

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane at 0 - 20℃;	92%
With hydrogenchloride; aluminium trichloride In dichloromethane

: 381-72-6
difluoroacetyl chloride

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 177361-22-7
2,2-difluoro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane a) 0 deg C, 4 h, b) RT, 3 h;	88%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 166322-31-2
6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Conditions

Conditions	Yield
With sulfuric acid; iodine; periodic acid In water; acetic acid at 80℃;	88%
With sulfuric acid; iodine; acetic acid; periodic acid In water at 70℃; for 6h;	85%
With sulfuric acid; iodine; periodic acid In water; acetic acid at 70℃; for 4h;	71%
With sulfuric acid; iodine; acetic acid; periodic acid In water at 70℃;
With sulfuric acid; iodine In water; acetic acid at 70℃;

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 1711-02-0
4-iodobenzoic acid chloride

: 185685-53-4
(4-iodophenyl)(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; Friedel-Crafts Acylation;	85%
With aluminium trichloride Yield given;

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

A: 92050-16-3
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine

B: 81864-05-3
2,3-diamino-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene

Conditions

Conditions	Yield
Stage #1: 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene With sulfuric acid; hydroxylamine hydrochloride In acetonitrile at 25℃; for 0.166667h; Stage #2: With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 25℃; Inert atmosphere; Sealed tube;	A 81.5% B 9%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 73183-34-3
bis(pinacol)diborane

: 853998-14-8
4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Sealed tube;	73%

: 5781-53-3
monomethyl oxalyl chloride

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 168301-02-8
Methyl 2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-2-oxoacetate

Conditions

Conditions	Yield
aluminum (III) chloride In dichloromethane at 0℃; for 2h;	71%
With aluminium trichloride	60%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 69008-41-9
6-(Chlorocarbonyl)-2-naphthalenecarboxylic acid,methyl ester

: methyl 6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)-2-naphthoate

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃;	69%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 610-14-0
2-nitrobenzyl chloride

: 188845-39-8
(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl-2-nitrobenzene

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 1.5h; Heating;	42%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 1663-67-8
malonoyl dichloride

: C31H40O2

Conditions

Conditions	Yield
With carbon disulfide; aluminum (III) chloride at 50℃; for 3h;	39%
With aluminum (III) chloride In carbon disulfide at 50℃;	39%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 79-30-1
isobutyryl chloride

: 102296-50-4
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl isopropyl ketone

Conditions

Conditions	Yield
Stage #1: 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene; isobutyryl chloride With aluminum (III) chloride In dichloromethane at 20 - 50℃; for 2h; Stage #2: With water In dichloromethane Cooling with ice;	38%
aluminum (III) chloride In dichloromethane at 20℃; for 3h;	38%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 79-03-8
propionyl chloride

: 112922-34-6
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone

Conditions

Conditions	Yield
Stage #1: 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene; propionyl chloride With aluminum (III) chloride In dichloromethane at 20 - 50℃; for 2h; Stage #2: With water In dichloromethane Cooling with ice;	27%
aluminum (III) chloride In dichloromethane at 60℃; for 3h;	27%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 13826-27-2
2,2'-bis(1,3,2-benzodioxaborole)

: C20H31BO2

Conditions

Conditions	Yield
Stage #1: 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene; 2,2'-bis(1,3,2-benzodioxaborole) With 2-chloro-1,3,2-benzodioxaborole; N-(2,2,2-trifluoroethoxy)phthalimide In acetonitrile at 25℃; Irradiation; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In acetonitrile regioselective reaction;	25%

...Expand

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

acryloyl chloride: acryloyl chloride

: 102296-82-2
2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethylcyclopenta[b]naphthalen-1-one

Conditions

Conditions	Yield
With aluminum (III) chloride; sodium hydroxide In 1,2-dichloro-benzene at 70℃; for 7.5h; Inert atmosphere; Cooling with ice;	21.3%

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 1,1,4,4-tetramethyl-decahydro-naphthalene

Conditions

Conditions	Yield
With nickel at 250℃; under 154457 Torr; Hydrogenation;

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 98-88-4
benzoyl chloride

: 102447-36-9
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl phenyl ketone

Conditions

Conditions	Yield
With aluminium trichloride; 1,2-dichloro-ethane

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

: 625-36-5
2-chloropropionyl chloride

: 102296-82-2
2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethylcyclopenta[b]naphthalen-1-one

Conditions

Conditions	Yield
With aluminium trichloride; 1,2-dichloro-ethane Erwaermen des Reaktionsprodukts mit H2SO4;

: 35951-36-1
2,6-dichloro-2,6-dimethylheptane

: 6683-46-1
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

A: 95488-93-0
1,1,5,5,8,8-Hexamethyl-4-isopropyl-1,2,3,4,5,6,7,8-octahydro-anthracen

B: 95557-93-0
1.1.5.5.8.8-Hexamethyl-4-isopropyl-1.2.5.6.7.8-hexahydro-anthracen

Conditions

Conditions	Yield
aluminium trichloride In carbon disulfide at 0℃; for 6h;

...Expand

1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene Specification

The 1,1,4,4-Tetramethyltetralin, with the CAS registry number 6683-46-1, is also known as naphthalene, 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-. Its molecular formula is C₁₄H₂₀and its molecular weight is 188.3086. Additionally, it has the systematic name 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene.

Other characteristics of the 1,1,4,4-Tetramethyltetralin can be summarised as followings: (1)ACD/LogP: 5.97; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.97; (4)ACD/LogD (pH 7.4): 5.97; (5)ACD/BCF (pH 5.5): 20277.3; (6)ACD/BCF (pH 7.4): 20277.3; (7)ACD/KOC (pH 5.5): 42125.41; (8)ACD/KOC (pH 7.4): 42125.41; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.49; (13)Molar Refractivity: 61.68 cm³; (14)Molar Volume: 213 cm³; (15)Polarizability: 24.45×10^-24cm³; (16)Surface Tension: 30.2 dyne/cm; (17)Density: 0.883 g/cm³; (18)Flash Point: 101.2 °C; (19)Enthalpy of Vaporization: 46.82 kJ/mol; (20)Boiling Point: 250.6 °C at 760 mmHg; (21)Vapour Pressure: 0.034 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: c1ccc2c(c1)C(CCC2(C)C)(C)C
2.InChI: InChI=1/C14H20/c1-13(2)9-10-14(3,4)12-8-6-5-7-11(12)13/h5-8H,9-10H2,1-4H3
3.InChIKey: CCQKWSZYTOCEIB-UHFFFAOYAG

Product Name

1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene

Synthetic route

1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene Specification

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