alpha,alpha'-Dibromo-p-xylene Chemical Properties

Melting point:

143-145 °C(lit.)

Boiling point:

245 °C(lit.)

Density 

2.012

refractive index 

1.614

Flash point:

155-158°C/14mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

dioxane: soluble1g/10 mL (hot)

form 

Crystalline Powder and Coarse Crystals

color 

White to beige

Water Solubility 

soluble, hydrolyses

Sensitive 

Lachrymatory

BRN 

1100019

CAS DataBase Reference

623-24-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1,4-bis(bromomethyl)-(623-24-5)

EPA Substance Registry System

1,4-Bis(bromomethyl)benzene (623-24-5)

Safety Information

Hazard Codes 

C

Risk Statements 

34-22

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3448 6.1/PG 2

WGK Germany 

3

F 

8-19-21

Hazard Note 

Corrosive/Lachrymatory

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:1,4-Bis(Bromomethyl)benzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

alpha,alpha'-Dibromo-p-xylene Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7055, 1994 DOI: 10.1016/0040-4039(94)88224-X

Synthesis

2.3.2.1 Synthesis of 1,4-bis(bromomethyl)benzene 4 In a 250 mL round bottom flask, p-xylene 1 (5 mL, 40.78 mmol) and 70 mL carbon tetrachloride were added as solvents. The flask was heated in an oil bath. Subsequently, N-bromosuccinimide (29.86 g, 167.80 mmol) and benzoyl peroxide (5.83 g, 24.08 mmol) were added sequentially to the flask. The reaction mixture was refluxed at 70 °C for 12 hours. Upon completion of the reaction, the solution was cooled to room temperature, at which point a solid imide precipitated, which was removed by filtration. The filtrate was distilled under reduced pressure to remove the solvent to give the light yellow solid product 1,4-bis(bromomethyl)benzene 4 in 90% yield with a melting point of 142-144 °C. The product was analyzed by FT-IR (KBr, cm^-1) showing 568 (C-Br stretching vibration), 1625 (C=C stretching vibration); 1H NMR (300 MHz, CDCl3) showing 4.28 (s, 4H, methylene proton), 7.18 (s, 4H, aromatic proton).

Purification Methods

Distil it under a vacuum and recrystallise it from EtOH, *benzene or chloroform. [Wenner Org Chem 17 527 1952, Beilstein 5 H 385, 5 I 187, 5 II 301, 5 III 859, 5 IV 970.]

References

[1] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6241 - 6244
[2] Tetrahedron Letters, 2005, vol. 46, # 41, p. 7047 - 7050
[3] Synthetic Communications, 2009, vol. 39, # 13, p. 2304 - 2309
[4] Journal of Molecular Catalysis A: Chemical, 2012, vol. 363-364, p. 81 - 89,9
[5] Polyhedron, 2012, vol. 47, # 1, p. 151 - 164

alpha,alpha'-Dibromo-p-xylene(623-24-5)Related Product Information

• Benzhydrylamine
• Diethylstilbestrol
• Decabromodiphenyl Ethane
• 4-Bromomethylbenzoic acid
• 1,3-Dibromo-5,5-dimethylhydantoin
• 1,2-Dibromopropane
• Benzyl bromide
• P-XYLENE
• 2,3,5,6-TETRAFLUORO-P-XYLENE
• Xylene
• 2,2-Bis(bromomethyl)propane-1,3-diol
• Musk xylene
• Benzene
• 1,4-BIS(BROMOMETHYL)NAPHTHALENE
• 4-BROMOMETHYL BENZOYL BROMIDE 96
• 1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE
• poly-p-xylene
• ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-P-XYLENE