| Identification | More | [Name]
alpha,alpha'-Dibromo-p-xylene | [CAS]
623-24-5 | [Synonyms]
1,4-BIS(BROMOMETHYL)BENZENE
A,A'-DIBROMO-P-XYLENE
AKOS BBS-00000840
ALPHA,ALPHA'-DIBROMO-1,4-XYLENE
ALPHA,ALPHA'-DIBROMO-4-XYLENE
ALPHA,ALPHA'-DIBROMO-P-XYLENE
LABOTEST-BB LT01772888
OMEGA,OMEGA'-DIBROMO-P-XYLENE
P-XYLENE DIBROMIDE
P-XYLIDENE DIBROMIDE
P-XYLYLENE BROMIDE
P-XYLYLENE DIBROMIDE
1,4-bis(bromomethyl)-benzen
1,4-Di(brommethyl)-benzen
1,4-Dibromomethylbenzene
p-(Bromomethyl)benzene
p-alpha,alpha'-Dibromoxylene
p-Bis(bromomethyl)benzene
p-Xylene, alpha,alpha'-dibromo-
Benzene, 1,4-bis(bromomethyl)- | [EINECS(EC#)]
210-781-1 | [Molecular Formula]
C8H8Br2 | [MDL Number]
MFCD00000182 | [Molecular Weight]
263.96 | [MOL File]
623-24-5.mol |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [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 |
| Hazard Information | Back Directory | [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 |
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