3,5-Dibromobenzyl bromide

3,5-Dibromobenzyl bromide Property

Melting point:

93-97 °C

Boiling point:

276.85°C (rough estimate)

Density 

2.1881 (estimate)

refractive index 

1.6340 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in toluene

form 

Powder

color 

White to beige-brownish

BRN 

3237827

InChI

InChI=1S/C7H5Br3/c8-4-5-1-6(9)3-7(10)2-5/h1-3H,4H2

InChIKey

PWTFRUXTAFBWBW-UHFFFAOYSA-N

SMILES

C1(Br)=CC(CBr)=CC(Br)=C1

CAS DataBase Reference

56908-88-4(CAS DataBase Reference)

Safety

Hazard Codes 

C-F,C,F

Risk Statements 

34-11

Safety Statements 

45-36/37/39-26

RIDADR 

1759

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

Precautionary statements

P234Keep only in original container.

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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.

P390Absorb spillage to prevent material damage.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

3,5-Dibromobenzyl bromide Chemical Properties,Usage,Production

Chemical Properties

white to beige-brownish powder

Uses

3,5-Dibromobenzyl bromide, is an important raw material and intermediateintermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

Under argon protection, (3,5-dibromophenyl)methanol (5.00 g, 0.021 mol) was dissolved in anhydrous tetrahydrofuran (250 mL), and the solution was cooled to 0 °C. Lithium aluminum hydride (1.62 g, 0.043 mol) was added slowly and in batches, followed by stirring the reaction mixture at room temperature overnight. Upon completion of the reaction, it was carefully quenched with water, ether (100 mL) was added and acidified with concentrated hydrochloric acid solution until the solid residue was completely dissolved. The reaction mixture was extracted with ether, the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give 4.31 g of the target product. The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3): δ 1.34 (s, 18H, tert-butyl hydrogen), 4.70 (s, 2H, benzyl hydrogen), 7.23 (d, 2H, J = 1.8 Hz, aromatic hydrogens), and 7.38 (t, 1H, J = 1.8 Hz, aromatic hydrogens). The crude alcohol (4.25 g) was dissolved in anhydrous dichloromethane (500 mL) and cooled at 0 °C. Triphenylphosphine (10.23 g, 0.039 mol) and carbon tetrabromide (12.93 g, 0.039 mol) were added sequentially, and the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction was quenched with water and extracted with dichloromethane. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was purified by fast column chromatography on silica gel using hexane as eluent to give 4.62 g (86% yield) of 1,3-dibromo-5-(bromomethyl)benzene.

References

[1] Chemistry - A European Journal, 2012, vol. 18, # 24, p. 7473 - 7485
[2] European Journal of Organic Chemistry, 2007, # 16, p. 2700 - 2712
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1215 - 1227
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237