2,4,6-Tris(bromomethyl)mesitylene Chemical Properties

Melting point:

187-189 °C (lit.)

Boiling point:

399.8±37.0 °C(Predicted)

Density 

1.759±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C12H15Br3/c1-7-10(4-13)8(2)12(6-15)9(3)11(7)5-14/h4-6H2,1-3H3

InChIKey

BHIFXIATEXVOQA-UHFFFAOYSA-N

SMILES

C1(CBr)=C(C)C(CBr)=C(C)C(CBr)=C1C

CAS DataBase Reference

21988-87-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

20/21/22-34

Safety Statements 

22-26-27-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

2903998090

MSDS

• Language:English Provider:SigmaAldrich

2,4,6-Tris(bromomethyl)mesitylene Usage And Synthesis

Uses

2,4,6-Tribromomethyltrimethylbenzene is used as an organic building block and a general reagent.

Synthesis

Under nitrogen atmosphere, 1,3,5-trimethylbenzene (0.7 mL, 5 mmol) was added to the reaction vial, followed by the sequential addition of acetic acid (2.6 mL) and 33% wt solution of hydrobromic acid acetic acid (3.5 mL). Next, paraformaldehyde (570 mg, 18.8 mmol, 3.7 equiv) was added. The reaction mixture was stirred at 95 °C. After 3 h, the solid was observed to start precipitating. Stirring of the reaction mixture was continued for 9 h, followed by cooling to room temperature. The reaction mixture was poured into ice water and the solid product was collected by filtration and dried. Recrystallization by mixed solvent recrystallization of dichloromethane and petroleum ether afforded the target compound 2,4,6-tribromomethyltrimethylbenzene as white needle-like crystals (1.99 g, 5 mmol, 99% yield).1H NMR (500 MHz, CDCl3) δ 4.61 (s, 6H), 2.50 (s, 9H).13C NMR (126 MHz, CDCl3) δ 137.84, 133.18, 29.93, 15.38.

References

[1] Journal of Organic Chemistry, 1993, vol. 58, # 5, p. 1262 - 1263
[2] Patent: WO2018/106112, 2018, A1. Location in patent: Page/Page column 70
[3] Synthesis, 1994, # 11, p. 1132 - 1132
[4] Organic Letters, 2009, vol. 11, # 11, p. 2229 - 2232
[5] Tetrahedron Letters, 2013, vol. 54, # 8, p. 771 - 774

2,4,6-Tris(bromomethyl)mesitylene(21988-87-4)Related Product Information

• Tricine
• 4-Bromomethylbenzoic acid
• Bromotrimethylsilane
• 5-Methyl-1H-benzotriazole
• Mesitylene
• 2-(Trifluoromethyl)benzoic acid
• 2-(Trifluoromethyl)benzaldehyde
• BUFFER SOLUTION PH = 6,00 (20 °C) (POTASSIUM DIHYDROGEN PHOSPHATE/SODIUM HYDROXIDE)
• 3-(Trifluoromethyl)benzaldehyde
• Tris(hydroxymethyl)aminomethane
• TRIMETHYL PHLOROGLUCINOL
• 3,5-Dimethylbenzyl bromide
• 2,5-DIMETHYLBENZYL BROMIDE
• 1,3,5-Tris(bromomethyl)benzene
• 2,4-DIMETHYLBENZYL BROMIDE
• 1-(BROMOMETHYL)-2,3-DIMETHYLBENZENE
• 4-Methylbenzyl bromide
• 4-Fluorobenzyl bromide