alpha,alpha'-Dibromo-p-xylene CAS 623-24-5

Introduction：Basic information about alpha,alpha'-Dibromo-p-xylene CAS 623-24-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

alpha,alpha'-Dibromo-p-xylene Basic information

• Product Name: alpha,alpha'-Dibromo-p-xylene
• Synonyms: 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-;P-XYLYLENE BROMIDE
• CAS: 623-24-5
• MF: C8H8Br2
• MW: 263.96
• EINECS: 210-781-1
• Product Categories: Aromatics;Miscellaneous Reagents;Aromatic Halides (substituted);Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 623-24-5.mol

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
• Fp: 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
• InChI: 1S/C8H8Br2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6H2
• InChIKey: RBZMSGOBSOCYHR-UHFFFAOYSA-N
• SMILES: BrCc1ccc(CBr)cc1
• 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: TSCA listed
• HazardClass: 8
• PackingGroup: III
• HS Code: 29039990
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
• Hazard Classifications: Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

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

106-42-3

623-24-5

2.3.2.1 Synthesis of 1,4-bis(bromomethyl)benzene 4In 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 Preparation Products And Raw materials

• Raw materials: Dichloromethane-->Carbon tetrachloride-->N-Bromosuccinimide-->Benzoyl peroxide-->Phosphorus tribromide-->P-XYLENE-->1,4-Benzenedimethanol-->NISTC502863-->Benzene, 1-(dibromomethyl)-4-methyl--->Bis(bromomethyl) ether
• Preparation Products: 1,4-Bis(imidazole-l-ylmethyl)benzene-->1,4-BENZENEDIMETHANETHIOL-->1,4-Phenylenediacetonitrile-->1,4-Bis(3-formylphenoxy)xylene