1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
- Product Name
- 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
- CAS No.
- 6683-46-1
- Chemical Name
- 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
- Synonyms
- 1,1,4,4-Tetramethyltetralin;1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE;NSC 17400;1,1,4,4-tetramethyl-2,3-dihydronaphthalene;1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-naphthalen;1,2,3,4-TETRAHYDRO-1,1,4,4-TETRAMETHYLNAPHTHALENE;1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalen;naphthalene,1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-;1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaline, tech;1,2,3,4-Tetrahydro-1,1,4,4-tetramethylnaphthalene, 97+%
- CBNumber
- CB4396352
- Molecular Formula
- C14H20
- Formula Weight
- 188.31
- MOL File
- 6683-46-1.mol
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene Property
- Melting point:
- 115-120℃
- Boiling point:
- 63 °C
- Density
- 0.9482 g/cm3(Temp: 27 °C)
- refractive index
- 1.5278 (589.3 nm 27℃)
- storage temp.
- 2-8°C
- form
- liquid
- color
- Clear, pale yellow
- InChI
- InChI=1S/C14H20/c1-13(2)9-10-14(3,4)12-8-6-5-7-11(12)13/h5-8H,9-10H2,1-4H3
- InChIKey
- CCQKWSZYTOCEIB-UHFFFAOYSA-N
- SMILES
- C1(C)(C)C2=C(C=CC=C2)C(C)(C)CC1
- EPA Substance Registry System
- Naphthalene, 1,2,3,4-tetrahydro-1,1,4,4-tetramethyl- (6683-46-1)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 20/21-36/37/38
- Safety Statements
- 23-26-36/37/39
- HS Code
- 2902900000
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 119707
- Product name
- 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
- Purity
- 95+%
- Packaging
- 1g
- Price
- $90
- Updated
- 2021/12/16
- Product number
- 119707
- Product name
- 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
- Purity
- 95+%
- Packaging
- 5g
- Price
- $252
- Updated
- 2021/12/16
- Product number
- CHM0017031
- Product name
- 1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $603.7
- Updated
- 2021/12/16
- Product number
- X0042
- Product name
- 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene
- Packaging
- 100g
- Price
- $760
- Updated
- 2021/12/16
- Product number
- CHM0017031
- Product name
- 1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE
- Purity
- 95.00%
- Packaging
- 5G
- Price
- $816.24
- Updated
- 2021/12/16
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene Chemical Properties,Usage,Production
Uses
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene can be used as an intermediate to participate in a variety of chemical reactions and is used in the synthesis of a variety of compounds and drugs. For example, 6-lodo-1,1,4,4-tetramethyl-l,2,3,4-tetrahydronaphthalene, 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and 1,1,4,4-tetramethyl-6-nitro-1,2,3,4- tetrahydronaphthalene and others.
Preparation
2,5-dichloro-2,5- dimethylhexane (300 mg, 1.64 mmol, 1 eq) was dissolved in dry benzene (25 mL). Then added AlCl3 (22.0 mg, 0.164 mmol, 0.1 eq) to the solution, which was stirred at reflux for 16 hours. The reaction was stopped with 3M HCl (5 mL) and extracted with hexanes (10 mL x 3). The combined organic layer was washed with brine, dried with Na2S04, filtered, and concentrated in vacuo. Finally, the crude was purified by flash chromatography (100% hexanes) to obtained the colourless oil (1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene).Yield=91%
Synthesis
6223-78-5
71-43-2
6683-46-1
General procedure for the synthesis of 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene from 2,5-dichloro-2,5-dimethylhexane and benzene: 2,5-dichloro-2,5-dimethylhexane (300 mg, 1.64 mmol, 1 eq.) was dissolved in dry benzene (25 mL). To this solution was added anhydrous aluminum trichloride (AlCl3, 22.0 mg, 0.164 mmol, 0.1 eq.) and the reaction mixture was stirred under reflux conditions for 16 hours. Upon completion of the reaction, the reaction was quenched with 3M hydrochloric acid (5 mL) and extracted with hexane (10 mL × 3). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated in vacuum. The crude product was purified by fast column chromatography (100% hexane as eluent) to afford 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (309 mg, 91% yield) as a colorless oil. The product was characterized as follows: 1H NMR (500 MHz, CDCl3) δ 1.33 (s, 12H), 1.74 (s, 4H), 7.16-7.19 (m, 2H), 7.34-7.36 (m, 2H, J = 2 Hz and 8.4 Hz); 13C NMR (500 MHz, CDCl3) δ 31.9, 34.2, 35.1, 125.5, 13C NMR (500 MHz, CDCl3) δ 31.9, 34.2 35.1, 125.5, 126.5, 144.8.
References
[1] Patent: WO2015/188015, 2015, A1. Location in patent: Page/Page column 31
[2] Patent: WO2018/107289, 2018, A1. Location in patent: Page/Page column 17
[3] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 1, p. 109 - 124
[4] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2182 - 2192
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 6, p. 1948 - 1959
1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene manufacturers
- Product
- 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydronaphthalene 6683-46-1
- Price
- US $101.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-28
- Product
- 1,2,3,4-TETRAHYDRO-1,1,4,4-TETRAMETHYLNAPHTHALENE 6683-46-1
- Price
- US $3.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 200KG
- Release date
- 2020-03-23