6683-46-1

Usage

Uses

Used in Fragrance Industry:
1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene is used as a synthetic musk substitute for its similar aroma, providing a cost-effective and sustainable alternative to natural musk in various fragrance formulations.
Used in Chemical Production:
1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene is used as a precursor in the production of other chemicals, contributing to the synthesis of a wide range of compounds for various applications.
Used in Organic Synthesis:
1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene is used as a chemical intermediate in organic synthesis, facilitating the creation of complex organic molecules for use in various industries, including pharmaceuticals, agrochemicals, and materials science.
It is important to handle 1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene with care, as it is flammable and may cause irritation upon contact with skin or eyes, ensuring proper safety measures are in place during its use in various applications.

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

Synthetic route

2,5-dimethyl-2,5-hexanediol (110-03-2) + benzene (71-43-2) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

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

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) + benzene (71-43-2) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

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%

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

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 → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

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%

1,1,4,4-Tetramethyl-tetralon-(2)-aethylenthioketal (97595-53-4) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

Conditions	Yield
With nickel In ethanol

2,5-Dimethyl-5-phenyl-2-hexanol (51510-58-8) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

Conditions	Yield
With sulfuric acid

aluminium trichloride (7446-70-0) + 2,5-dimethyl-2,5-hexanediol (110-03-2) + benzene (71-43-2) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + 1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydroanthracene (22306-30-5)

aluminium trichloride (7446-70-0) + 2,5-dichloro-2,5-dimethyl hexane (6223-78-5) + benzene (71-43-2) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

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

1,1,4,4-tetramethyl-decahydro-naphthalene + benzene (71-43-2) + platinum-coal → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

Conditions	Yield
at 350 - 375℃;

2,5-dimethyl-2,5-hexanediol (110-03-2) → 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1)

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

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

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + acetyl chloride (75-36-5) → 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethanone (17610-21-8)

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-sulfonyl chloride (132392-26-8)

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;

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethanone (17610-21-8)

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%

methyl 4-(chlorocarbonyl)-2-fluorobenzoate (1190848-41-9) + 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → methyl 2-fluoro-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 1,1,4,4-tetramethyl-6-nitro-1,2,3,4-tetrahydro-naphthalene (102121-55-1)

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (27452-17-1)

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-oxo-2-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthalenyl)acetate (142675-64-7)

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

difluoroacetyl chloride (381-72-6) + 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 2,2-difluoro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone (177361-22-7)

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (166322-31-2)

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℃;

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + 4-iodobenzoic acid chloride (1711-02-0) → (4-iodophenyl)(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanone (185685-53-4)

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine (92050-16-3) + 2,3-diamino-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene (81864-05-3)

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane (853998-14-8)

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%

monomethyl oxalyl chloride (5781-53-3) + 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → Methyl 2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)-2-oxoacetate (168301-02-8)

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + 6-(Chlorocarbonyl)-2-naphthalenecarboxylic acid,methyl ester (69008-41-9) → methyl 6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)-2-naphthoate

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + 2-nitrobenzyl chloride (610-14-0) → (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl-2-nitrobenzene (188845-39-8)

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + malonoyl dichloride (1663-67-8) → C31H40O2

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + isobutyryl chloride (79-30-1) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl isopropyl ketone (102296-50-4)

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + propionyl chloride (79-03-8) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone (112922-34-6)

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%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) → C20H31BO2

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + acryloyl chloride → 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethylcyclopenta[b]naphthalen-1-one (102296-82-2)

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%

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 1,1,4,4-tetramethyl-decahydro-naphthalene

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + benzoyl chloride (98-88-4) → 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl phenyl ketone (102447-36-9)

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

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) + 2-chloropropionyl chloride (625-36-5) → 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethylcyclopenta[b]naphthalen-1-one (102296-82-2)

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

2,6-dichloro-2,6-dimethylheptane (35951-36-1) + 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene (6683-46-1) → 1,1,5,5,8,8-Hexamethyl-4-isopropyl-1,2,3,4,5,6,7,8-octahydro-anthracen (95488-93-0) + 1.1.5.5.8.8-Hexamethyl-4-isopropyl-1.2.5.6.7.8-hexahydro-anthracen (95557-93-0)

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

Upstream product

• 6223-78-5 2,5-dichloro-2,5-dimethyl hexane 
• 71-43-2 benzene 
• 97595-53-4 1,1,4,4-Tetramethyl-tetralon-⁽²⁾-aethylenthioketal 
• 51510-58-8 2,5-Dimethyl-5-phenyl-2-hexanol 
• 110-03-2 2,5-dimethyl-2,5-hexanediol 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 27452-17-1 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene 
• 132392-26-8 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-sulfonyl chloride 
• 185685-53-4 (4-iodophenyl)(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanone 
• 188845-39-8 (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-carbonyl-2-nitrobenzene 
• 92050-16-3 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine 
• 94497-51-5 Am80 
• 94497-53-7 methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-carbamoyl]benzoate 
• 116232-94-1 4-<(3-amino-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl>benzoic acid 
• 116232-93-0 4-<(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-nitro-2-naphthalenyl)carbamoyl>benzoic acid 
• 71441-40-2 p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl>-benzaldehyde 
• 71441-30-0 p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl>-benzyl alcohol 
• 71441-43-5 α-methyl-p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzyl alcohol 
• 71441-32-2 p-<(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl>-benzyl methyl ether 
• 71441-28-6 TTNPB 

Relevant academic research and scientific papers

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Compounds described herein are inhibitors of retinoic acid inducible P450 (CYP26) enzymes, and are useful for treating diseases that are responsive to retinoids. Certain compounds have retinoid activity, are resistant to CYP26-mediated catabolism, and are used for treating diseases that are responsive to retinoids.

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