4-broMo-1,2-bis(broMoMethyl)benzene

4-broMo-1,2-bis(broMoMethyl)benzene Property

storage temp. 

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

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C8H7Br3/c9-4-6-1-2-8(11)3-7(6)5-10/h1-3H,4-5H2

InChIKey

PJYGXPFKKAJUBG-UHFFFAOYSA-N

SMILES

C1(CBr)=CC=C(Br)C=C1CBr

Safety

RIDADR 

3261

HazardClass 

8

PackingGroup 

Ⅲ

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

4-broMo-1,2-bis(broMoMethyl)benzene Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-bromo-1,2-bis(bromomethyl)benzene from 4-bromo-1,2-xylene: To a 1000 mL round-bottomed flask were added 4-bromo-o xylene (0.0811 mol, 15.0 g), N-bromosuccinimide (NBS, 0.0426 mol, 7.580 g), 2,2'-azobisisisobutyronitrile (AIBN. 0.00405 mol, 0.6650 g) and 500 mL of carbon tetrachloride (CCl4). The reaction mixture was heated to reflux for 1 hour. Subsequently, NBS and AIBN were added in four additional portions.After completion of the reaction, the reaction mixture was filtered while hot to remove the precipitate and the filtrate was concentrated. The crude product was purified by hexane crystallization to give white crystals (23 g, 93% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.53 (d, 1H, ArH, J = 2.0 Hz), 7.44 (dd, 1H, ArH, J = 8.1 Hz, J = 2.0 Hz), 7.24 (d, 1H, ArH, J = 8.1 Hz), 4.60 (d, 4H, CH2, J = 4.2 Hz).

References

[1] Patent: WO2008/24435, 2008, A2. Location in patent: Page/Page column 98
[2] Journal of Organic Chemistry USSR (English Translation), 1985, p. 1418 - 1421
[3] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 7, p. 1556 - 1560
[4] Patent: WO2015/103508, 2015, A1. Location in patent: Page/Page column 102
[5] Journal of Organic Chemistry, 1979, vol. 44, # 9, p. 1519 - 1533