6-BROMO-1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE Chemical Properties

Melting point:

34 °C

Boiling point:

110-115°C

Density 

1.165±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

Water Solubility 

Insoluble in water

InChI

InChI=1S/C14H19Br/c1-13(2)7-8-14(3,4)12-9-10(15)5-6-11(12)13/h5-6,9H,7-8H2,1-4H3

InChIKey

NLOOVMVNNNYLFS-UHFFFAOYSA-N

SMILES

C1(C)(C)C2=C(C=C(Br)C=C2)C(C)(C)CC1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

23-26-36/37/39

Hazard Note 

Harmful

HS Code 

2902900000

6-BROMO-1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE Usage And Synthesis

Uses

6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene is used in Synthesis and evaluation of synthetic retinoid derivatives as inducers of stem cell differentiation.

Synthesis

The reactor was cooled to 0 °C under nitrogen protection. A mixture (90 mL) containing 2,5-dichloro-2,5-dimethylhexane (110 g, 600 mmol) and aluminum bromobenzenesulfonate (7 g, 52.5 mmol) was added slowly and dropwise to the reactor. After dropwise addition, stirring of the reaction mixture was continued for about 20 minutes. Subsequently, the reaction mixture was extracted with 1 L of a mixed solution of ether and hexane (1:1 v/v). The organic layer was washed sequentially with ice water, 10% hydrochloric acid and 100 mL of brine. After separation of the organic layer, the solvent was removed by concentration under reduced pressure. The residue was dried with magnesium sulfate to give a brown oil. Finally, the target product 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene was purified by methanol crystallization to obtain 120 g in 80% yield.

References

[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2930 - 2941
[2] Patent: US2005/4213, 2005, A1. Location in patent: Page 25
[3] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5302 - 5305
[4] Patent: KR101515814, 2015, B1. Location in patent: Paragraph 0292; 0293
[5] Tetrahedron, 2005, vol. 61, # 20, p. 4755 - 4759

6-BROMO-1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE(27452-17-1)Related Product Information

• Molybdenum
• 2-bromotetralin
• 6-BROMO-1,1,4,4,7-PENTAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE
• 6-BROMO-1,1,4,4-TETRAMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENE