1,3,5-TribroMo-2,4,6-TriMethyl-Benzene

1,3,5-TribroMo-2,4,6-TriMethyl-Benzene Property

Melting point:

225.5-226.5℃

Boiling point:

329.3±37.0 °C(Predicted)

Density 

1.910±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Heated), Hexanes (Slightly, Heated)

form 

Solid

color 

Pale Grey to Light Grey

InChI

InChI=1S/C9H9Br3/c1-4-7(10)5(2)9(12)6(3)8(4)11/h1-3H3

InChIKey

LTSSSVHTLGQZAQ-UHFFFAOYSA-N

SMILES

C1(Br)=C(C)C(Br)=C(C)C(Br)=C1C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1,3,5-TribroMo-2,4,6-TriMethyl-Benzene Chemical Properties,Usage,Production

Uses

1,3,5-Tribromo-2,4,6-Trimethylbenzene is a useful reagent for preparing highly durable superhydrophobic nanothorn arrays.

Synthesis

General procedure for the synthesis of 2,4,6-tribromo-1,3,5-trimethylbenzene from 1,3,5-trimethylbenzene: 1-methoxy-3,5-dimethylbenzene (100 mg, 0.73 mmol), N-bromosuccinimide (NBS, 260 mg, 1.46 mmol), and a stainless steel ball (5 mm in diameter) were placed in a 10 mL stainless steel grinding jar. The ball milling reaction was carried out and the reaction process was monitored by thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). Upon completion of the reaction, the reaction mixture was transferred to 30 mL of ethyl acetate and cooled at 0 °C. The product in the filtrate and the precipitated spent succinimide were separated by filtration through filter paper. The filtrate was concentrated under vacuum to give 250 mg (85% yield) of 2,4,6-tribromo-1,3,5-trimethylbenzene as a colorless powder. To test the efficiency of the large-scale reaction, a monobromination reaction was also carried out with 1.3 g of 1-methoxy-3,5-dimethylbenzene for 1 h. The product was isolated in 87% yield. During the reaction, the grinding equipment was suspended and a small amount of sample was removed from the reaction tank for TLC and 1H NMR analysis, after which the reaction was continued, and the time of this operation was not included in the total reaction time.

References

[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[2] Organic Letters, 2003, vol. 5, # 4, p. 549 - 552
[3] Tetrahedron Letters, 1997, vol. 38, # 20, p. 3499 - 3502
[4] Journal of Materials Chemistry A, 2017, vol. 5, # 18, p. 8292 - 8296
[5] Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 652 - 656