1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE

1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE Property

Melting point:

159-161 °C(lit.)

Boiling point:

326.93°C (rough estimate)

Density 

2.168

refractive index 

1.7040 (estimate)

storage temp. 

Refrigerator, under inert atmosphere

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)

form 

Crystalline Powder

color 

Off-white to light yellow

CAS DataBase Reference

15442-91-8(CAS DataBase Reference)

Safety

Hazard Codes 

C

Risk Statements 

34-36/37

Safety Statements 

26-27-28-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE Chemical Properties,Usage,Production

Chemical Properties

off-white to light yellow crystalline powder

Uses

1,2,4,5-Tetrakis(bromomethyl)benzene has been used in the synthesis of:

• tetrapodal imidazolium ligands as their PF₆^? salts
• 6,7-bis(bromomethyl)-2,11,18,21,24-pentaoxatetracyclo[23.4. 0.0^4,9.0¹²,¹⁷]nonacosa-1(25),4(9),5,7,12 (17),13,15,26,28-nonaene
• conformationally constrained cyclic α-amino acid derivatives
• thiacyclophanes
• dendrimeric organoplatinum complexes

Synthesis

General procedure for the synthesis of tetrabromotoluene from 1,2,4,5-tetramethylbenzene: 1,2,4,5-tetrakis(bromomethyl)benzene (2.8 g, 20 mmol) was prepared by reacting 1,2,4,5-tetramethylbenzene (2.8 g, 20 mmol) with N-bromosuccinimide (NBS, 14.4 g, 80 mmol) and benzoyl peroxide in 50 mL of tetrachloromethane (1c, 1 g, 5.9 mmol). The reaction mixture was heated at 77 °C for 50 min. After completion of the reaction, the precipitate was collected by filtration under reduced pressure and washed with hot tetrachloromethane. The filtrate was concentrated to a small volume and cooled to 4 °C. The crude product was filtered and purified by recrystallization from methanol. The reaction time was less than 1 hour to give a white solid product in 15% yield with a melting point of 159-160°C. The structure of the product was determined by 1H-NMR (CDCl3, δ: 7.37 ppm, 2H, a; 4.60 ppm, 8H, b), 13C-NMR (CDCl3, δ: 137.6 ppm, a; 133.6 ppm, h; 28.7 ppm, b), and FT-IR (KBr, νmax: 3026, 2980, 2933. 1504, 1456, 1210, 911, 797, 678, 598 cm-1) were characterized.

References

[1] Journal of the Chinese Chemical Society, 2002, vol. 49, # 1, p. 77 - 82
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 26, p. 4281 - 4286
[3] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 247, p. 23 - 30
[4] Heterocycles, 2015, vol. 90, # 1, p. 645 - 658
[5] Tetrahedron Letters, 2015, vol. 56, # 26, p. 3992 - 3995